SCIENTIFIC ABSTRACT MIKHAYLOV, B. M. - MIKHAYLOV, B. M.

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• Collection: Scientific Abstracts
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• Release Decision: RIF
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• Document Creation Date: November 2, 2016
• Document Release Date: July 13, 2001
• Sequence Number: 3
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

5, (70
A - T'
- C ~-rkiqyan, 1'.
TTL-. o%,cri, C-i-mr-7s 1---o1jy(.,novyy-_, rovc~in~nir,'
, 0 Co m -n ion
of Ar-rlpolvenv Eyllroc-~rlbons by ~'eaw,
-,-,n 'intez
arilpoliyenovykh u-1(-!.:,)-.-)r!o1. T)r:l culcolic),i -ictal'-iDrganich-sk-i.~h
F-'?Tl V F)S:3R. 01 !-Ianiyu ni-.u:
USSR)
.I in talc of
r. n ium,, rL L cRcfi 1, 2) 9,;~ r-
P-nl in;
,nvc~7tir~ated: benzy! .30-I'll-. 7- 1 C :,MDO ln~ 2 hC-rZ.,-
cinnamic alin~i.vlc, m-iethy'- nn, 7 1 n n
c e t c n-i n ' c i n n n 7n
phenyl.hexq.1 1 r-ne- :-on-2 s r,
inventigntion -,f syntl~eo_;-. 7~ -n
s !-,-rn tl~~.-3i7- 1 nCr-or,! ing I c
Ref The e-cporimental part s,- -,,3 it _es-ri- ir r
,>rd 1/' synihnsig of the individual substanri-. lh~, r - 7

polyune Compounds. Communication 1. 3ynthosis Af Cv/", ; - -,--,
Aryl po I.Vene Fydrocarbons by 'Ae an 3 of Organom,~till', i -: Compo Ira iS
for the preparation or the in', . v:- , :_1 !,,
the s'vnt)ipSi3 benzyl 7;Alum w 'i - ' 1.~c _ '0 - -1,: "-
in 1 v2- c)osition nnd methylcinriamic 1-ly(! e FL
un.gnturated krtone whicli i-.L.,j ;L
carbonyl gr-ui). Tho attach:v!r~. -J
acetonhont, locl- in th~,
l,ptonr. r- rt,,i ~:i th (x-T)icolY' t ~l i i;:- I n
lith,i~rn rpac*o ' i~ tl~ I)enz:,! i , cinnr7~_i'j
th- for- '.i-)n -,f* crkr')inr,'. :n corinertior
hydro-(:nati n cl' ti~- IF--tt9r, 11 --1 c, tale
hydroc-,irlonr: o 7f-,vr , n 7., for-is c~'
XV I I! I w ~ -,i in~,d . The fol' --
.P,. the comr-,un~
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/ I
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50)
1UTHOMr B. Me, Tutorakays, F. B. MV/62-39-6-29/36

TITLE: Derivatives of 1,5-Diboroayclooctane Cllroizvodnyye
.1 , 5-dibortaiklook-tana)
FMODICALt XzTestiya Akademii nauk SSSR. Otdeleniye khimichesldkb nauk, 1959,
Nr 6, pp 1127 - 1130 (USSR)
ABSTR&CTt In one of the author's earlier papers written in cooperation
with Shobegoleva (Ref lj,, he showed that the olefins with
triisobutylboron form substituted' borotrialkyls. In this
connection the reaction of triisobutylbcron and triallylboron was
investigated. It is asmmed that this reaction leads to the
formation of a e3yclic compoluad of the following compositionr
,'02 "~2 CS2
,
3- CH2 CH2 CH 2- B (1)
N CH2CH2 CH2/
In the reaction mentioned, polymers at first formed, itich, by the
aztJon of alcohols, transformed into 1,5-dialkoxy-1,5-diborooycloootme.
Tbos lattiwr Txaated with ettiylamine under formation of
Gard 1/2 1,5-di(ethylani:lne)-1,5-diborocyal,-wtane. In the experimental part

DerivatiTes of 1,5-Diborooy-.1o3otane SCV/62-59-6-29/36
the produotion of the different substances is described in
detail. III experiments were oarried out in a nitrogen
atmosphere. The physical constants of the different compounds
produced are giren, There are 3 Soviet references.
L'33OCTATICV t Insti-tut organichaskoy kh1mii im. U. D. Z/.Linskogo Ak:.,1emii
nauk SSSR (Institalva of Organic Chemiistry imeni IS. 'j. Zelinskiy
of the loademy af Scie~:-,ces, USSR;
SUBMITTEDt Deoembez I~ 1558
Card 2,/2

5 (3)
ARTHORS: Mikhaylov, B. M., Savellyeva, 1. S. ~C)V/6 2-5' - "' --21138
TITLE: On the Influence of Thioacetir Acid Dn kniles and Azobenzene
( 0 deyetvii tioukausnoy kisl.-)ty na anily i az-.benzc)l')
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1959, Nr 7, Pp 1304 - 1306 (USSR)
A13STRACT: Mikhaylov and Blokhina (Refs 1,2) showed in a previous papsT
that polycyclic and aromatically substituted ethjlere hy4rc-
carbons enter into a conjurrated. reaction with thioa2etic acid
in the presence of oxygen under formation of dithiloacetyl- )r
oxythioacetyl- hydrocarb,~n derivatives. The formatior pron~'ss
of these compounds is investigated in the present pa rer in the
case of the transformation of the azomethine compounds under
the influence of thicacetic acid ani in the preeence of mole-
cular oxygen. Benzophenone anile in thioacetic acid sol,.~t!~-n
vehemently absorbs oxygen. The reaction mixture is hoated and
changes its color. The reaction is fin-shed with the absorp-
tion of the equivalent quantity of oxygen. The authors otain-
ad: acetanilide, benzophanone, diacetyl-disulphila, and
Card 1/~ The reaction proceeds according to the following scheme:

On-the Influence of Thioacetic Acid on Aniles and sov/62-59-7-21,130
Azobenzene
(C 6H5)2 C-NC 6H5+ 3CH3COSH + 02. C6H5NECOCH 3+(C6H5)2CO +
+ (C11 3COS)2 + 3 + H20 (1). The affeot of benzophanone anii~ ir
thioacetic acid in the case of laiking of oxygen was Lnvestl-
gated in order to clarify the intermediate stages of the
ass. It was found that the intermediate compoundo a.-a acet~,n_'__
lids and thiobenzophenone (reaction scheme 2). The ruact!~-;n
process between acetopheaone anile and thioaoetic a-14 j
analogous. The mentioned change in color (during thL- rea.-tion,
into blue) proves thA formation of thlobenzophanone .is jl,-ter-
mediate product. Diacetyl-dioulphide, sulphide, and hy1:,(,Lt?!!
sulphide are produced from thioacetic acid during th~ i4?a-
tion. N-aoetyl-hydrazobanzene is formed in the cast-
of azobenzene with the threefold equivalent of
following 3cheme: C H,N-NC4R
according to the 6
C6H5 ITH-NC 6H5+ (CH 3COS)2 1- H2S (4).
1
COCH3
Card 2/3

On the Influence of Thioacetic Acid on Arlilos and SCV/62-5?-7-21/30
Azobenzene
The reactions are described in detail in the experimental pai,t.
There are 7 references, 2 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii im. N. D. ZelinskoGo Akademiinauk
SSSR (Institute of OrGanic Chemistry imeni It. D. Zolinskiy of
the Academy of Sciences, USS11)
SUBMITTZD: November 11, 1957
Card 3/3

50)
AUTHORS: Mikhaylov, B, M., Shchegoleva, T. A. SoV/62-59-8-8/42

TITLE: Boron-organic rompoundo. Communication 42- Alkylpyro-boro-
acetic Anhydrides
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1959, Nr 8, pp 1393-1396 (USSR)
ABSTRACT: It was shown in the present paper that the mixed anhydridpq
of fatty acids and n-propylpyro boric acid normally formed
under the influence of organic acid8 upon eqters of n-propyll-
chloro boric acid may be obtained much more easily by heating
alkyl boric acid with the anhydride of acetic acid over a
water bath. In this way it was possible to synthesize the
anhydrides of n-propylpyro-boroacetic acid (I), isopropyl-
pyro-boroacetic acid (II), and n-butylpyro-boroacetic acid
(III) as well as isobutylpyro-boroacetic acid (IV), with
yields ranging between 60 and 70% of the theoretical yields.
The compounds obtained were investigated as to their different
reactivities. It was shown that the anhydrides of alkylpyro-
boroacetic acid easily react with the eaters of alkyl boric
acid at 160-1650, forming the anhydrides of alkyl boiic acid,
Card 1/2 The anhydride of n-propylpyro boric acid forms a mixture of

Boron-organic Compounds. Communication 42: Alkylpyro- SOV/62-59-8-8/42
boroacetic Anhydrides
anhydrides of propyl and phenyl boric acids when heftted with
the esters of phenyl boric acid. The anhydride of n-propyl-
pyro boric acid forms anhydride of propyl boric acid also with
the esters of n-propylchloro boric acid. In the experimental
part the reaction method is described. There is 1 Soviet
reference.
ASSOCIATION: Institut organicheakoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR (Institute of organic Chemistry imeni N. D. Ze-
linskiy of the Academy of Sciences, USSR)
SUBMITTED: November 21, 1957
Card 2/2

50)
AUTHORSt Mikhaylovt B. 9., Fedotov, N. S. sov162-rq-8-24/42
TITLE: Complex Compounds of Diphenyl Boron Chloride With Primary Amines
and N-Substituted Derivatives of Diphanylamino Boron
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1959, Nr 8, PP 1482-1483 (USSR)
ABSTRACT: The present paper is a continuation of investigations made
concerning the reaction of diarylborochloride and amines (Ref 1).
The primary amines form, in contrast with the secondary amines,
complexes with the above compounds where two amino molecules are
to be found for each chloride molecule:
(C6H5)2 BCl + 2HNH2' (R6 H5)2 BC1.2RNH2
R being CH,-, C 2H5-9 i-C4H9
So far, these compounds had been unknown. Similar compounds
(alkylboron difluorides with two alcohol molecules) had been
obtained by Mikhaylov and Shchegoleva (Ref 3). The structure of
the molecules obtained here is considered either a hydrogen-bond
structure (II) or heteropolar (III). The saline character and the
Card 1/2 low volatility suggest (III). When the temperature is raised

Complex Compounds of Diphenyl Boron Chloride With sov/62-59-8-24/42
Primary Amines and N-Substituted Derivatives of Diphenylamino Boron
above the melting point, the molecule decomposes and forms
N-substituted diphenylamino boron (IV) and alkylamino chloride.
Compound (I)(R - CH 3) changes when left undisturbed into the
crystalline dimer which is probably of a cyclic structure M.
The existence of the complexes investigated and their thermal
transformation throw some light upon the r4action mechanism of
the substitu.;ion for the chlorine atoms at the amino group in
boron-organic halogenides. The experimental part describes in
detail the individual transformation reactions. There are
3 references, 2 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii im. N.D. Zelinskogo kkademil, nauk
SSSR (Institute of Organic Chemistry imeni N. D. Zelinskiy of the
Academy of Sciences, USSP)
SUBMITTEDs December 17, 1958
Card 212

SOV/b 1 -0 _.~-121,d
AUTHORS: Nikitina, A.N., Galanin, M.D., Ter-Sarkisyan, G.S. and
Mikhaylov, B.M.
-------------------------------- -
TITLE*, The Absorption and Luminescence Spect:a of Solutions of
Substituted Pclyenes (Spektry pogloshcheni7a i
lyuminestsentsiya rastvorov nekotorykh zameshchennykh
poliyenov)
PERIODICAL, Optika i Spektroskopiya, 1959, Vol 6, Nr 3, pp 354-66,~,
(USSR)
ABSTRACT: The authors investigated the electronic absorption spectra
of eighteen substituted butadienes and hexatrienes dissoived
in heptane as well as luminescence of solutions of these
substances in heptane and benzene. All the substances
studied were purified chromatographically using aluminium
oxide. The absorption spectra of solutions were measured
using a spectrophotometer SF-4. The luminescence spectra
in the visible region were meaaured by means of a spectro-
meter consisting of a monochromator UM-2 and a photo-
multiplier FEU-19. The results obtained are shown in TaDle
1. This table includes calculated values of the oscillator
Card 1/2 strengths of long-wavelength electronic transitions and the

SOV/ 01-6 -6-1212b
The Absorption and Luminescence Spectra of Solutions of Substituted
Folyenes
quantum yields of luminescence. The absorption spectra of
solutions of the substituted butadienes and hexatriones are
shown in Figs.1-8. It was found that the absorption
intensities and band positions depend on the degree of
departure from coplanarity of conjugated double bonds. it
was found also that the quantum yield of luminescence of somo
substances is higher In benzene solutions and in others It Is
higher in heptane solutions. Measurements of the excited-
state lifetime showed that decrease of the quantum yield of
1,1,4,4-tetraphonyl-butadlene-1,3 in a benzene solution Is
due primarily to quenching of the second type, while uhanges
of the excited-state lifetime of 1,6-diphenyl-hexatriena-l,',",b
cannot be explained by quenching (Table 2). There are 8
figures, 2 tables and 11 references, of which 2 are Soviet,
8 English and 1 Germar,
SUBMITTED: January 16, 1968
Card 2/2

5 (3)
A U B. M.
TITL:~: Organic Compounds of Boron
P1:210LICAL: Uspe"dii khimii, 1959, Vol ',0, r 1~',
j,8~1'2,,AUT: in this survey, work in the fivid of' oro. compoun.
published from 1956 to 1956, m(~, i-I --x', in 1"159 i.';
sumo.arized. Work on the inve~;tij:: tionf; %crf2r:.c~* cn ooroa
con, pounda without boron-carbon -,uc~ :-.z boric acic oi ;rz,,
its iuAdeo etc. is included. reluted to t,A~-
tonic were, for the major part, discuriocc~ in ,~ rcc.-.rtly
published paper (Ref 2) on the rcactir)r, of boron cl-lori(i-- :it'r
organic compounds. In thio paper, at "~ 1 of
boron trialkyls (:-~efa 1, 3, A to 39), b3-,-%,z
42 to 46) as well as their properties (- s 4,7-5", 13, 2,-)
are described. The physical pro-~articz, o-- :;yin..etric '-zh t' ~0
cor.-)oui-ida are r-iven in table 1, of z~tric onrs i.i
cu-,d 3. 'I'he second part of this paper in -:-.-oto(! to t.e o7.1
deriv,tivec of organoboron eompour!ds i%volviri_- ;-,onoc-LLbStit-:tk2--1
organoboric acids and their derivi,tiv- ~ efs 1, ~-3, 53 to
The physical properties of some ;-oi.ocul.z-,titutod crL-'~anoboric
Card 1/4 acids recovered are u=,iarized in tablo 4, of their anhyt'12-iLesv-111,

Orgenic Compounds of Boron
507/74-28-12-22/2~
in table 5, and of their eaters in table 6. Moreover,
disubstituted orgrnoboric acids and their derivatives are
treated. Methods of preparation used for disubstituted
organoboric acid esters (Refs 16, 28, 44, 54, 55, 97, 105-118),
their proFerties (Refs 87, 108 to 110, 119 to 122), mothuds of
preparation and properties of disubstituted organoboric acids
and their anhydrides (Refs 16, 40, 41, 44, 86, 108 to 110,
123 to 126) are described. The physical properties of
disubetituted organoboric acids are summarized in table 7, of
their anhj-drides in table 8, of ti-e esters of symmetric -.acids
in table 9, and of the eaters of asymmetric acids in table 10.
The third sootion deals v'with the I:aloderivativeB of or,3,-Iio-
boron compounds. Lethods of preparation used for halo-
derivatives of organoboric acids (Refs 1, 28, 37, 41, 4,',
96, 96, 99. 101, 102, 110, 112, 116, 119, 120, 127, 12P ':)
143) as vrell as their properties (aefa 14, 74, 95, 1011 Il'-),
112, 134, 137, 139 to 141, 144 to 146) axe described. T',.,,
ph,vaical properties of different types of haloderivativen :;f
orgenoboron compounds are given in tables 11 to 14. In t-,c
fourth aection, the thioderivatives of or~vviioboron cornpj,~-,-c are
Card 2/4 briefly discussed (Hefs 1, 16, 148 cc 151 . Properties oi.
.. Ll~

Drf.anic Compounds of Boron
esters of organic thioboric acids arc given in tables 15 ~_.d
16. In the fifth section of the paper, the nitrogen deriv.-tivc-,
of organoborozi compounds, i.e. borazoles (Refs 1, 16, 28, loo,
102, 132, 147 to 149), are troat6d by the author. Physicad.
properties of 112 MIR type or.-wioboron compounds are given
table 17, of RB( 'Ill?) 2type or.-ano~,oron compounds in teble
I
of the arino esters of RB_,OR. type organoboric acids in tai)ic 19,
`NR'
and of tri- and hexasubstituted borczole derivatives in table 20.
The lively interest in orgwioborori corAp(.,,-.ds is attributed to
both their theoretical importance for orgwiie c 'hemistry ~-nd to
their practical pon.,iibilities for ap-,"lication. For their
heating pover, boron hydridoo ~nid or-anoboron compounds zxc
high-grade propellants for jet en~-,ines. Polyboronorcanorilox-~..i2r,
and boron- cont aining organic pol~!.crs can be obtained fro:-.
organoboron compounds. Organoboron co;.,-,ounds are being used in
fluid scintillators to record neutrons (.1ef 175). They can be
of importance to biology and medicine also (Refs 69, 176). The
author repeatcl,11.; refers to his avrn papers, and cites the
Card 3/4

Orgwlic Co-pow-,('Is of JI-oron
- -12'~
names of the folloaing Soviet scientists: T. A. ,hc;:-i'~,:oluva,
L. 1. Zakharkin, 0. Yu. Okhlobystin, V. A. Vaver, 1'. :~~.
Aronavich, 11. S. P4dotov, Yu. N. Bubnov, A. F. Zh+la~:-., L. N.
Koclineva. There are tarilee and 176 references, C) oi which
are Soviet.
AS~;OCIATION: In-t organicheskoy khijaii im. N. L. Zelinsko-o 01 Sj5-
(Institute of Organic Chemistry ime i N. D. ~elinskiy,,,~.~ U6.3R)
Card 4/4

AUTHORS: Mikhaylov, P. _'hernova, N. SOV,7-'-29-1-471174
TITLE: On Dioxane- ind Diotane Benzene Complexes of the Lithium-
Aromatic Compoui.da (0 dioknanovykh i dioksancivo-benzollnykh
kom,plekcakh litiyaromaticheskikh noyedineniy)
PE R 1 " D I ~.' A-L Zhurnal obshchey 1,i7nii, 1 Vol 'Ir 1
pp C-22 - 228 (U3511?)
A!~STRACT: The autnors synthosized the (~()rnplex compounIs of lirhium
aryls with dioxane (Ref 1) to begin vith 1y mixing the
benzene solution of n,butyl lithium ~rith t,e lioxqre
solutions of axyl, bromi~le according to t.'e sche-ne
ArBr+n.-C4H9Li -~- ArLi+n.-C4H9 Br. The share of dioxane
in the compounds thus obt;iined was calculated by deter-
mining their metal content and in the case of deriv~,tives
of the solid hydrocarbons by deter-mining the hydrogen rhare.
In the case of investi,-ation of the dioxane complex of
3-pyrenyl lit*-,ium (Ref 2) n-it only the getal -tnd the hydro-
carbon conter~ were detirmined but also the dioxane itself.
In this conrection it wan f,)un! th,t thiv complex contitinn
Card 1/3 also anothc-r ijroc!i_,ct ipart from dioxane. Baqin.- upon this

On Dioxane- and Dioxane Benzene Complexes of the SOV/79-29-1-47/74
Lithium-Aromatic Compourde
observation also the earli(r obtained complex rompourAs
of lithium aryls were quantitatively investi.:Atpd with
respect to dioxane in which conTection it was found that
in some of them thk- riourt of lithium iryl -ind fiioxare
amounted to 72-n(,"-' of the complex -i,,Pi,:ht. Tnus, the cor-
cluFion wa.9 drawn tl..t 1,erzer-e whir-h eas used ris solvert
forms also part -)f the complox (Ref 2). T0-les I and 2
may serve aa illustration-- of this case. Sum-arizing, the
following investi:--ttion rc,:~ult-- -ir(, t- be --entio-ird: In
the case of action of bc.-zero -olution of n-butyl lithium
upon aryl brom-Aes in t'~e pr,~sence of lioxane, dioxaT:e-
benzene com;~Iexes of the lithium-aro-natic compounds of
the composition 2ArLi.2C 4Ha02- C(I H6are for-ned. These
complexes f~r-- ph-,.-i-;-l lit-ium, p-tolyl lit,Aum, o-to'. '11
lithium. p-r.loroph,,nyl lithium n,. 3-pvrenyl lithium.
9-phenanthryl lithium --in(] 9-anthryl lithium form ~orre~,~ord-
inr,ly Vie c-mplexpa ArLi.C H 01, nnd ArLi.2P- H 0 In
0 4 8 ' 4 8 2'
the case of action of th-a hexare nolution of n.-butyl
Card 2/13 lithium upon the aryl bromides in the pr,-,,,;enre of dioxane

On Dioxane- and Dioxane Benzene Complexes of the SOV/79-2i-1-47/74
Lithium-Aromatic Compounds
the complexes 2 ArLi-3C 4Ha02 or ArLi.2C 4H802 are obtained.
Thus the nature of the solvent exercises an influence upon
the composition of the dioxane complexes of the lithium-
aromatic compounds. Th,re are 3 tables and 13 r--fer-erces,
8 of which are Soviet.
ASSOCIATION: Institut eksperimentallnoy patologii i terapii ra?,a
(Institute of Experimer.tal Cancer Pathology and Therapy~
SUBMITTED: November 5, 19'17
Card 3/3

50) . so V/7 9-2~, -4 - 48,'77
AUTHORS: Mikhaylov, B. M., ArDnovicl--,, P. 11.
TITLE: Organo-borcn ComToun-,s 1Borcrgan.JC".e3kiye
XXXIV. Alkylphenylboron Chlorides (AIIkilfenJI'Iborkh.nri,iy
PERIODI CAL Zhurnal obshchey khimii, 19'~q, Vol 29, Nr 4, pp 12'41-1,--~~7
(USSR)
A.BSTRACT: The authors ~~ontinued the-ir w~,rk in the field i~f th~-
of organo-boron compounds of the fatty arDm~it-.c acf-.ec 'Ref
and synthesized, during th, -iircrk '113CUSJt~i ,,. this fir-
the isobutyl ester of etK~-Lpl,enyi ~cric Lic"'i "II)
formation of lithium ethylate with phen~! lb-c-r-c
7
C6H5B(OC 4H9 )2 * C9HFIL~-' --a- CgHr
B'0c'H :'I
I -> 1+ 9
~C2 H51
L- W
BOC 4H9 (II)
Card 1/ 3 C2 H5..>

SOV/79-29-4-4-8171
Organo-boron Compounds. XXXIV. Alkylphenylboror, C'-Ioriies
It was shown that the ethylphenyl di-isabutoxyboreniate of
lithium (I), which forms ir, the first stage, decomposes n'-t
only with HC1 but also with diluted hydrochloric a~'id. S'.1--h a
simplification is also possible in the synthesis of the eskers
of n-propylphenyl- and n-butylphenyl boric acid, since the
lithiumalkylphenyl di-isobutoxyboreniates, in contra3t with
the diphenyl di-isobutoxyboreniates of lithium (Ref 5), dp-
compose in one direction only with diluted h3~drochloric a,:id,
while the esters of alkylphenyl boric acids are formed simu-
taneously. The isobutyl esters of alkylphenyl boric acids are
equally stable in the hydrolysis as the alkyl esters of di-
alkyl- and diaryl boric acids (Refs 4,5,6). By reaction with
Pcl 5 the alkylphenylborates change into alkylpheny! boron
chlorides (76-83~6 yield). The reaction follows the scheme:
BOC H + PCI, BC1 + POCI iso-C H9r-i
4 9 4
C H C
6 5 6 5
Card 2/3

SOV/79-29-4-48/77
Organo-boron Compounds. XXXIV. Alkylphenylboron Chlorides
In this way the methylphenyl-, ethylphenyl-, n-pr,~py.phs-,,ryl-
and n-butylphenyl boron chlorides were prepared. There: Arf-
I table and 8 reference3, 6 of which are Soviet.
ASSOCIATION: Institut organicheakoy khimii Akademii nauk SSSR
of Organic Chemistry of the Academy of 3ciences USSR)
SUBMITTED: February 24, 1958
Card 3/3

50) SCV/79-29-4-4~177
AUTHORS, Mikhaylov, B. M., kronovich, P. M.
TITLE: 0rgano-boron Compounds (Bororganicheskiye soyedineniya).
XXXV. Alkylphenyl Boric Acids and Their Anhydrides (MV. Al-
kilfenilbornyye kisloty i ikh angidridy)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 4, pp 1257-1262
(USSR)
ABSTRACT: With the exception of a paper published by K. Tors3ell ~Ref 1),
in which the reaction conditions and constants of the synthe-
sized product were not given, alkylphenyl boric acids have ao
far not been described. As has been reported (Ref 2), the
authors did not succeed in r~-alizing the hydrolysis of the
Jsobutyl esters of alkylphenyl boric acids. During a further
attempt to obtain alkylphenyl boric acids through the influBnce
of water on alkylphenyl boron chlorides (Ref 2) it was found
that the nature of the alkyl radical exerts a great influence
on the behavior of these chlorides with reauect to water.
When reacting with water ethylphenyl boron chloride does not
form, as expected, ethylphenyl boric acid but only ethyl boric
Card 1/3 acid. Among the further negative cases only n-butylphenyi

SOV/79-29-4-49,'77
Organo-boron Compounds. XXXV. Alkylphenyl Boric Acids and Their An~~,-irides
boron chloride reacts normally with water, and the ccrrespond-
ing acid in formed. The hydrolysis mechanism of alkylphenyl
'boron chlorides is apparently connected with the procx~s3es of
a complex formation, as usually observed in boron compounds
chemes (0. (2), and (3)]. Compound (1) fir3t affillates
e water'moiecule and forms the complex compound 411)
R
splits off HC1 and thus changes into (III). in ti-i a ;:rjcess
(II) splits off benzene, and (IV) is formed. These results cf
the hydrolysis with water show that benzene can only ~e pre-
vented froa.being split off by binding the hydrogen chloride
removed in the course of the reaction. Indeed, it was possible
to obtain the alkylphenyl boric acids by saponification of
the chlorides with an equimolecur&r umount of alkali 1,ye. '.;!,~en
distilled, the methyl-, ethyl-, and n-propylphenyl boric acids
split off water and form anhydrides. In this process n-hutyl-
phenyl boric acid disproportionates. Thus, by th- hidr~:-I~j3is
of alkylphenyl boron chlorides with water a mixt,,~re j'L i1kj",'L-
phenyl- and alkyl boric acid is formed. There are 41 tabips
and 5 references, 3 of which are Soviet.
Card 215

SOV/79-29-4-.49/77
Organo-boron Compounds. XXXV. Alkylphenyl Boric Acids and Their Anhydrides
ASSOCIATION: Institut organicheskay khimii Akademii nauk SSSR (Institute
of Organic Chemintry of the Academy of Sciences-USSR)
SUBMITTED: February 24, 1958
Card 3/3

501
AUTHORSt Mikhaylov, B. M., KoBtroma, T. V. SOV/79-29-5-15/75
TITEE: Organoboron Compounds (Bororganicheskiye soyedineriya).
36. Synthesis of Hexasubstituted Compounds of norazolo Prom Fa--~ers
of the Aryl-chloroborio Acid (36. Sintez geksaz-iireshcheni,-~,-n
borazola iz efirov arilkhlorbornykh kislot,'
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 5, pp 1477-1493 NSSTQ
ABSTRACT: In order to devise a method of synthesizing "bort~.z(;P' derivatives in
the present paper thermal transformations of some eaters of ;tryl-
ethyl-amino-boric acids as well as of aryl-phanyl-amino-boric acids
were investiga,..,4. By the influence of ethyl amine upon ~-.ters of
the aryl-chloroboric acid isobutyl eaters of the p-toluoi,o-ethyl-
amino-borio, o-toluenevethyl-amino-boric and atrnaphthyl-ethyl-arino-
borio uld were obtained. The opinion expressed in refererice I
regarding the transformation mechanism of the esterL: Lf the aryl-
ethyl-amino-boric acid into Oborazol" compounds and eaters of the
aryl-borio acid was revised. It was concluded that OborazolO
compounds are formed by separation of alcohol directly from amino
eaters (I). Further the alcohol reacts with the initial amino ester
thus forming the ester of aryl-boric acid and'ethyl-amine. Owing to
Card 114 this reaction ono half of the ester of the aryl-athyl-amino-boric

Organoboron Compounds. SOV/79-29-5-15/75
36. Spithesis of Hexasubatitutod Coupounds of "Borazoll From Eaters of the
Aryl-c&loroborio Acid
acid must be converted into the Oborazol* compound and the other
into the eater of the aryl-boric acid which really took place. This
reaction mechanism was confirmed by the ready transformation of
aryl-bis-(ethylamino)'boron (11) into B-triaryl-N-triethyl-borazol,
which took plaae in thepresence of small alcohol quantiti4s. The
experiment indicated that phenyl-bi a- (athylodno) - boron is transformed
into B-triphanyl-N-triethyl-borazal on heating up to 2600 in the
presence of small amounts of butyl alcohol. The yield is 85%.
Without alcohol its yield is only 17% (Ref 2). With aniline the
eaters of the aryl-chloro-borio acid yield the aniline hydrochloride
and eaters of aryl-phenyl-aminoboria acid which can, however, not be
prepared in a pure form. During distillation in vacuum at 15-20 mm
they are cleaved to give aniline, eaters of the &ryl-boric acid and
B-+.riaryl-11-triphenyl-bore,zole. In this way the hexaphenyl-borazol
was obtained from the ester of the phenyl-boric acid (30%) and the
?,tri-p,-td*I-&tfipheny1 borazol (39.4%) from the ester of the
p-tolVI-ohloroborio acid and aniline. The formation mechanism of
boraiol compounds from esters of the aryl-phenyl-aminoboric acid
Card 2/4 differs from the mechanism of the thermal transformation of eaters

Organoboron Compounds. SOV/79-29-5-15/75
36. Synthesis of Hexasubstituted Compounds of norazolO From Eaters of the
Aryl-atkloroborio Acid
of the aryl-athyl-aminoboric acid. In contrast with the latter they
are cleaved at about We symmetrically into esters of the a.-yl-
boric acid and aryl-bio(phenylamino)boron (VI) which are trarsformed
at 300-4000, after separation of aniline, to give hexaaryl-borazols.
In this way the phenyl-bia(phenylamino)boron (79.4%)' was obtained
from esters of the phenyl-phonylamino-boric acid and the p-tolyl-
bia(phonylamino4boron (83.6%) from the esters of the p-tolyl-
phenyl-aminoboric acid. In accordance with the mechanism mentioned
"borazol" compounds are formed from amino esters (V) in the same
yield (about, 30%) as on thermal decomposition of aryl-bie(phenylardno-)
boron. The phanyl-bis-(phenylamino-)boron is converted in the
presence of small amounts of butyl alcohol into hexaphenyl-borazols
in the same yield as without alcohols. All "borazol" derivatives
obtained possess a stability unusual for organoboron compounds with
respect to atmo~opheric -xygen and moisture. There are 2 Soviet
references.
ASSMIATIOSt Institut organicheskoy khimii Akaf-aii nauk WSR
card 3/4

Organoboron Compounds. SOV/79-29-5-15/75
36. Synthesis of Hexasubstituted Compounds of "Borazol" From Raters of the
Aryl-chloroboric Acid -
(Irstitate of Organic Chemistry of the Academy of Sciences, USSR)
SUMITTED: February 24, 1958
Card 4/4

5(3) S V,179-29-5-i6/75
AUTHORSs Mikhaylov, B. M., Blokhina, A. N., Kostroma, T. V.
TITLE: Organoboron Compounds (Bororganichoskiye soyedineniya). 37-SYn-
thesis of B-Triarylborazols From Aryl Boron Dichlorides (37.
Sintez B-triarilborazolov iz arilbordikhloridov)
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 5,
Pp 1483 - 1486 (M;R)
ABST---ACT: Reference I describes the reaction of phenylboron-dictiloride
with ammonia, where B-triphenyl borazel in formed. In the
present paper it was found that also other aryl-boron dichlorides
react with ammonia in a similar way. The samples required for
the investiL:-ation were prepared by means of reaction of aryl-
boric acid eaters with phosphcrus pentachloride, p-chloro-
phenyl-boron dichloride and p-brrmo-phorLyl-boroi-lichl3ri(le. ',.n
introduction of ammonia into benzone solution of aryl.-bk-r n-
dichliride its ammoniate is formed at room temperature. On
heating its benzene su3pension in t~.e water bath P-A on con-
tinued introduction of ammonia the ammoniate is 'rurZrrmed into
ammonium chloride and B-triaryl-borazol. I:.i this vayB-tri-p-
Card 1/2 tolyl-borazol, B-tri-p-chloroplieyi,,,l-bornzol arid B-tri-r)-bromo-

Organoboron Compounds. 37. Synthesis of B-Triarylborazole S~ V/75-2~~-',,-l -, 75
From Aryl Boron Dichlorides
phenyl-borazol were obtained in yields of 65 - 91-,,'.. 2',e .cti~)n
mechanism probably consists o: a traiiLiformation of tl-,4,,
boron dichloride initiallL fo=erl (1) ixito
boron (II). The molecules of th.:~ latter condense -.-.,ith c1(,
other and form triaryl-borizol. The B-triaryl-borazols i-:v
extre,rely stable with reopect to atmG,,~pheric moioture oxy-
gen as compared with other orE:anoboron comPounds. The pl:~-r.~-I-
boron-dichloride yields con.-lox compounds witll. triet?.yl-an-Jz:(,.
There are 3 references, 2 of wl.ich are Soviet.
ASSUCIATNN: Institut oruanic~,eskny khimii Akader.-Iii nauk (Instilt:te
of Organic Chemistry of tLe Acad(-my of Sciences,7,':.,'I-
SUM=-LD: February 24, 1958
Card 2/2

50)
AUTHORS: Mikhaylov, B. M., Ter-Sarkisyan, G. S. SOY/79-29-5-50/75
TITLE: Polyene Compounds (Poliyenovyye soyedineniya).
VII. Condensation of Vinyl -Ethyl-Ether With the Acetals of
Aromatic Aldehydes and Ketones (Kondensatsiya viniletilovogo
efira a astetalyami aromaticheskikh alldegidov i ketonov)
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 5, pp 1642-1648
(USSR)
ABSTRACT: As a first example in the series of aliphatic-aromatic ketones
the authors investigated the reaction between diethyl ketal of
acetophenone and the vinyl-ethyl-ether. This reaction is much
more complicated than the one between adetale of aromatic
aldehydes and a,p-unsaturated ethers. The following was
iaolated from the mixture: 3-phenyl-1,1,3-triethoxy butane,
5-phenyl-1,1,5-triethozy hexene-2, T-phanyl-1,1,7-triethoxy
octadiene-2,4,9-phenyl.-1,1,9-triethoxy-docatriene-2,4,6 and
diethyl acetal of acetal aldehyde. The structure of 3-phenyl-
1,1,3-triethoxy butane was proven by saponification with
diluted hydrochloric acid to 3-phenyl-3-ethoxy-butanal-1 and,,
Card 1/2 under heavier conditions, to P-methyl cinnamaldehyde.

Polyene Compounds. VII. Condensation of Vinyl-Ethyl- SOV/79-29-5-50/75
Ether With the Acetals of Aromatic Aldehydes and Ketones
In order to determine the position of the ethoxy group in
5-phenyl-1,1,5-triethoxy hexene-2, the diethyl acetal of
P-methyl cinnamaldehyde was entered into reactioL id1hvinyl ethyl
ether and 5-phenyl-1,1,3-triethoxy hexene-4 was obtained
therefrom. Both hexene derivatiVes (hexcne-2, hexene-4)
were hydrolyzed and the aldehyde obtained was identified by
its 2,4-dinitrophenyl hydrazone. Moreover, hexene-2-derivative
was obtained by direct synthesis from acetophenone acezal and
1-ethoxy butadiene-1,3. Both higher condensatior products
were not investigated more closely. The experimental
describes the reactions carried out and gives the physical
and analytical data of the initial substanoes as well as of
the compounds obtained. There are 8 references, 1 of which
is Soviet.
ASSOCIATION: Institut organicheskoy khimii Akademii nauk SSSR (Institute
of Organic Chemistry of the Academy of Sciences of the USSR)
SUBMITTED: April 15, 1958
Card 2/2

50)
AUTHORS: Mikhaylov, B. M., Bubnov, Yu. N. SOV/79-29-5-51/75
TITLE: Boron Organic Compounds (Bororganicheakiye soyedineniya).
XXXVIII. The Reaction of Boron Trialkyls With Sulphur.
Synthesis of Esters of the Dialkyl-Thio-Boric Acids
(XXXVIII.Reaktai.ya bortrialkilov s seroy. Sintez efirov
dialkiltiotornykh kislot)
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 5~PP 1648-1650
(USSR)
ABSTRACT: The authors investigated the problem, to what extent there
is a parallel between the reaction of boron trialkyle with
sulphur and with oxygen. Experiments showed that tri-n.-
propyl boron and tri-nrbutyl boron with sulphur on heating
UP to 1450 supply the corresponding di-e6ters of thioboric
acid: R 3B + 3 ---* R2BSR. In analogy with the reaction with
oxygen trialkyl boron probably forms first a molecular
compound with sulphur, which then enters reaction with a
second molecule of trialkyl boron: R 3B + Sn - R3BIC- S n
Card 1/3 ' Publications hitherto
B 96 : S
B a 2R
+ R
BSR + S
R
n-2
n
2
3
3

Boron Organic Compounds. XXXVIII, The Reaction of SOV/79-29-5-51/75
Boron Trialkyle With Sulphur. Synthesis of Esters of the Dialkyl-Thio-
Boric Acids
revealed only the methyl ester of dimethyl thioboric acid,
which however was obtained from the reaction between methyl
mercaptan and tetramethyl diborane or dimethyl boron bromide
(Refs 2,3). Esters of dialkyl thioboric acids are uneffected
by temperature changes and very reactive. In water they
hydrolyze to dialkyl boric acids; under the effect of alcohols
they form esters of dialkyl boric acids. Thus, methyl ester
of di-n propyl*boric acid was obtained from the n.-propyl ester
of di-n:-propyl thioboric acid and methyl alcohol. Esters of
dialkyl thioboric acids react with amines under formation of
dialkyl boramine substituted at the nitrogen. In this way, the
authors obtained di-n.-propyl loobutyl amino boron and di-n.-
butyl phenyl amino boron. The experimental contains the
exact description.of the reactions mentioned as well as the
analytical and physical data of the substances obtained.
There are 3 referencas.
Card 2/3

Borbn Organic Compounds. XXXVIII. The Reaction of SOV/79-29-5-51/75
Boron Trialkyle With Sulphur. Synthesis of Estero of the
Dialkyl-Thio-Borio Acids
ASSOCIATION: Institut organicheskoy khimii Akademii nauk SSSR (Institute
of Organic Chemintry of the Academy of Sciences of the USSR)
SUBMITTED: April 9, 1958
Card 3/3

5 ( 34
AUTHORS: Mikhaylov, B. M., Povarov, L. 5. SOV/79-29-6-66/72
TIME: Polyene-Compounds (Poliyenovyye soyedineniyu). VIII. Reactions
of Some Acetals With Unsaturated Ethers (VIII. Reaktaii
nekotorykh ateetaley a nepredellnymi efirami)
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 6, pp 2079 - 2083
(USSR)
ABSTRACT: It was recently discovered, that acetals can react with ethers,
which have conjugated double bonds, and form products, which
are bound to the diene in position 1,4 (Refs 1-6). These reac-
tions have been used in the present study for the synthesis of
some derivatives of aldehydes of the terpene series. It was
proved, that citral acetal (1) reacts smoothly in presence of
zinc (II) chloride with the compound (II), forming acetal (M
and acetal (IV) according to Bcheme 1. The compound (III) is a
derivative of farnesol, and (IV) a derivative of di-terpene
aldehyde. The reaction of the a, 0-unsaturated ethers with ace-
tale was used for the synthesis of acetal (VIII ). The acetal
VI) has been condensed in presence of zinc (11) chloride with
V), forming (VII). This compound has been co'n7erted by conden-
~
Card 1/2 sation with vinyl ethyl ether into acetal of the 3,5 di-ethoxy-

Polyene -Compounds. VIII. Reactions of Some Acetalip SOV/79-29-6-66/72
With Unsaturated Ethers
3,7-di-mothyloctane-6-ol-7 (VIII). This final product is the
acetal of di-ethoxy citronellal(scheme 2). The authors obtain-
ed the initial product (II) by the effect of catalytic quanti-
ties of the n-toluol sulphonic acid in quinoline upon butane
(IX). This method could also be used for the synthesis of the
I-ethoxy butadiene-1,3 from 1,1,3-tri-ethoxy butane. The com-
pounds (X and(XI) were obtained by condensation of the com-
pound (IX~ with vinyl ethyl ether (scheme 3). There are 7 ref-
erences, 5 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii Akademii nauk SSSR (Institute
of Organic Chemistry of the Academy of Sciences, USSR)
SUBMITTED: July 22, 1958
Card 212

5 (3)
AUTHORS: Mikhaylov, B. It., Fedotov, N. S. SGV/7)-2)-7-3C/,~3
TITLE: Organoboron Compounds (Bororganicheskiye soyedineniya). 7XXV-1.
Asymmetrical Diaryl Boric Acids and Their Derivatives (xxxv-1.
Nesimmetrichnyye diarilbornyye kisloty i ikh proizvodnyye)
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 7, FI) 2244 -- 2248
(USSR)
ABSTRACT: One part of the diaryl boric acids form com-,lex C0,21POUnds aith
water of the type Ar 2B'_-OH
'~-OH2
(A) the other part contains no
water, it has, however, the effect of Lewis acias in aqueous
solutions, i.e. with bases they form the same si-Its (B) as the
acids of the hydrate form (A). The authoro continued their in-
vestigation of the complex formation in the series of aromat--'c
boron compounds and synthesized some unsymmetrical diaryl boric
acids, their eaters, and acid chlorides, and investiGated their
capability of complex formation. The Isobutyl eatero of unsyn-
metrical diaryl boric acids (V) were synthesized by tlie rc-ar-
Card 1/3 tion of the correspondink; GriCnard rea[;(3nts tYc

/9 1;
Organoboron Compounds XXXVI . Asymmetrical Diaryl SCV/7~-2'~_7 -3C,
Boric Acids and Their Derivatives
eater of phenyl boric acid (Scheme 1). In this case the iso-
butyl esters of phenyl-p-tolyl-, phenjl-p-bromophenyl-, and
phenyl-a-naphthyl boric acid were obtained. These esters form
stable complex compounds (G) with ammonia. The isobutyl esters
of phenyl-p-tolyl- and phenyl-a-naphthyl boric acid were trans-
formed with PCI5 into the chlorides, phenyl-p-tolyl boron
chloride and phenyl-a-naphthyl boron chloride (ScLeme 2). "he
diaryl boron chlorides form the followinE solid complex com-
pounds with dioxane (1:1): phenyl-p-tolyl boron chloride-,
phenyl-a-naphthyl boron chloride- as well as diphenyl boron
chloride and di-a-naphthyl 'boron chloride dioxanate (Ref 4)
(Scheme 3), which were synthesized already earlier. In the
hydrolysis of the phenyl-a-naphthyl- and phenyl-p-tolyl borcn
chloride, the phenyl-a-naphthyl- and phenyl-p-tolyl boric acid
are formed which contain no complex water (Scheme 4). The lat-
ter acid is extremely unstable and decomposes accordinC to
scheme 5. There are 5 Soviet references.
Card 2/3

Organoboron Compounds. MVI. Asymmetrical Diaryl SOV/79-23-7-3C/83
Boric Acids and Their Derivatives
ASSOCIATION: Institut organicheskoy khimii Akademii nauk SSSR (Institute
of Dreanic Chemistry of the Academy of Sciences, USSR)
SUBMITTED: Juie 18, 1958
Card 3/3

5 0) JOY/ 19-2 5
AUTHURS: Vaver, V. A.
TITLE- urganoboron Compounds (bororganicheskiye uoyedinuniya).
XXXVII. Lithium Salts of the Diaryl Boric Acids an,' TI.eir
Uomplex Compounds with vioxane tXXXVII. Litiyevyye soli
aiarilbornykh kislot I ikh komplekBnyje sojedineniya .3 diolcaanom)
PERIODICAL: Zhurnal obshchey khimii, IV59, lol 29, Nr 1, ;:p 22,jd-21'),),' kUzi3ri)
ABSTRACT- In continuation of earlier investigations the authors show
that diaryl boric acids react like protonic acids in annydroui
media. Unexpectedly they obtainea the lithium salt of di-x-
-naphthyl boric acid ~t-C luH/)2 oOLi kil an tne main product in
the reaction of phenyl lithium with qi--z-naphtny1 r)or4C acid.
'rhis salt is formed even more iasily from n.-bUtyl 1"'thium and
di-a-naphthyl boric acid in )enzene solution k3cheme 2). 'rne
reaction of n.-butyl lithium with di-o-tolyl boric acid k3cheme 5A
which leads to the formation of a mixture rrom the lithium 3alts
of di-o-tolyl- and o-tolyl butyl boric acid, is much more
complicated. Their formation is exnlainea by the decomposition
of compound kill), in contrast to k1l), under the separation of
Card 1/3 butane and toluene. With diox~,ne in abnolutely anny1rous ether

Organoboron Uompounds. AXXVII. Lithium aults of' .5uv/ 19-~?I- 1- 51/,135
the Maryl Boric Acids and Their Uomplex GomFounds ivith Dioxane
it' was possible to separate t'rom thi3 3alt mixture the -ure
lithium salt of the di-o-tolyi boric acid in the form of its
complex compound with dioxane. The lithium 3alt of o-toiyl-
hutyl I-,oric acid could not be separated,iti pr-,~qen-~e, nowever,
was found to lie probably due to the resultant per cent content
Of boron kRet's 40). in order to prevent the lormatiun of calto
of aryl bUtyl boric acidi, only o-toiyi or p-ioiyi lithium were
used in the experiments tor obtaining the lithium salts of
ni-o-tolyl- and di-p-tOlyl boric acid. rrie nece~i.,ary inlividual
or:,anoilthium compounds were obtained by th,~ reaction of n.-
-butyl litnium with aryl bromides in benzene dioxane solution
and In the form of their crystalline dioxanates (Ref 6). The
p-tolyl lithium was synthesized from n.-butyl lithium and
tri-p-tolyl antimony (Ref 6). By this method the lithium salt
of di-p-tolyl boric acid and the dioxanate of the lithium salt
of the di-o-tolyl boric acid were obtained. TI.e dioxanate3 Of
the lithium salts of the diaryl boric aciqs may be 3.-;itheqizf--d
,!irectly by the reaction of lithium compounds Nitl~ the dioxarates
Card 2/5 of tht- diaryl boric acids (e. g. compound (V) accurdin,~ to

Organoboron Compounds. XXXVII. Lithium Salts of 3O7/(q-2V-7-31/b3
the Diaryl Boric Acids and Their Complex Compounds With Dioxane
scheme 5). There are 7 references, 6 of wt,ich are 3oviet.
A3SOCIATION: Institut organicheskay Khimii Akademii nauk SSjR (Institute
of Organic Chemistry of the Academy of Sciences, USJR)
SUBMITTM June 26, 145d
Card 3/3

5M SOV/79-29-8-22/81
AUTHORS: Mikhaylov, 4. M., Ter-Sarkisyan, G. S.
TITLE: Polyene Compounds. IX. Condensation of Acetals of Furyl-, Cin-
namic- and Furyl-acrylic Aldehyde With Unsaturated Ether3
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 8, pp 2560-2565
(USSR)
ABSTRACT: In addition to previous papers (Refs 1,2), the present paper
deals with the condensation of the diethyl acetals of the abc,:e-
mentioned aldehydes with the vinyl ethyl ether and I-ethoxy-
butadiene-1,3. The reaction of these diethyl acetals with a,-V
unsaturated ethers takes place readily in the presence of the
acetic acid -alution of zinc chloride, and yields the ccrrespon--
ing ethoxy derivatives of the aromatic and furane series wl,lct
by boiling with acetic acid (Ref 3), are easily transformed
into the unsatura.'ed aldehydes. The reactions of the diethy-'
acetals of the above-mentioned aldehydes with vj.nyl ethyl ether
gave, in fair yields, the condensation products of acetal,
mostly with one molecule of vinyl ethyl ether already at equi-
molar ratios of the reagents. Thus, the diethyl acetal of the
Card 1/~_ cinnamic aldehyde reacts with this ether under formatiDn of

qov/79-29-8-22/81
Polyene Compounds. IX. Condensation of Acetals of Puryl-pCinnamic- and Fur-11-
acrylic Aldehyde With Unsaturs~~ed Ethers
compound (I) which is transformed, by boiling with glacial
acetic acid, to give (II) in good yield. This method is of
preparative importance, and better than the previous conden-
sation according to reference 4 (Scheme 1). Compound (III) can
be obtained as easily, which is transformed by boiling with
acetic acid into the acrolein (IV) which had formerly been syn-
thesized from furfurole and acetic anhydride (Ref 5) (Scheme 2).
The reaction of compound (V) with vinyl ethyl ether gives (VI),
and further, with acetic acid, pentadienal (VII) (Scheme 3).
On reaction of the double quantity of diethyl acetal of the
cinnamic aldehyde with 1-ethoxy-butadiene-1p3v compound (Vil'.).
resulted which further gives compound (IX) by boiling with
acetic acid (Scheme 4). Further compounds of this kind (X)-
(XIII) were synthesized for the first time (Schemes 5,6,7).
There are 7 references, 2 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii kkademii nauk SSSR (Institute
of Organic Chemistry of the Academy of Sciences, USSR)
Card 211-

50Y SOV/79-29-9-67/76
AUTHORS: Mikhaylov B M Aronovich, P. M.
TITLE: Organoboron Compounds. X LV. Reaction of Butyl Esters of
Boric Acid and Boronorganic Acids With kromatic Amines
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Ur 9, pp 3124-3129
(USSR)
ABSTRACT: The present investigation was made to explain the capability
of alkoxy groups of the esters of boric acid and their deriva-
tivee of being replaced by amino groups. Experiments proved
that these esters react with aromatic amines at their boil-
ing point. The reaction takes place under the formation of
the corresponding amino derivatives in the following manner:
+ 3C
H
OR
H
+ 3 RNE
B(OC
0 B(NHR)
)
2
3
4
9
9
3
4
RIB(Oc 4 H9)2 + 2 RNH2 ===� R1 B(U'TR)2 + 2C4YH
R1 BOC H + RITH R'2BNHR + C4 H 9OR
2 4 9 2 e---
Herefrom it follows that these are reversible reactions. The
transformation of the eater into the amine can only be achieved
Card 1/3 by eliminating the alcohol from the reactant. The alcoholysis

SOV/79-29-9-67/76
Organoboron Compounds. XLV. Reaction of Butyl Eaters of Boric Acid and
Boronorganic Acids With Aromatic Amines
of the amino derivatives takes place much zore rapidly than
the substitution of the amino groups for the alkoxyl as
exemplified by t4he reaction of phenyl di--(phenylamino)-boron
(IMC H ) j . When the alcohol is separated from the
[(C6115B 6 5 2
reactant by distillation, the above-.mentioned reactions take
place only if amines are used that have a higher boiling point
than the alcohol formed in the reaction. In the present paper
the reactions of the isobutyl eaters of borio, n.-propyl, phenyl,
and diphenyl boric acid as well as of the nrbutyl eaters of
n.-butyl, and di-n:-butyl boric acid with aniline and p-toluidine
are described. Hereby only those prolucts "ere obtained in
which all alkoxy groups were full substituted, which could
be explained by stage (1) and (II~ of the reaction. The resultR
obtained prove that the substitution rate of the aryl amino
groups for the alkoxy groups in the esters of boric, phenyl
boric, and diphenyl boric acid is inverse to the rate of hydro-
lysis of the sam6 eaters (Refs 7, 8). The follovin6 compounds
were synthesized in this way: tri-(p-tolylamino)--boron, phenyl
Card 2/3 di-(phenylamino)-boron, phenyl di-(p--tolylamino)-boron, n--propyl

SOV/79-29-9-.67/76
Organoboron Compounds. XLY. Reaction of Butyl Eaters of Boric Acid and
BoroAorganic Acids With Aromatic Amines
di-(phenylamino)-boron, nrbutyl di~phenylamino)-boron, di-
pbenyl-(phenylamino)-boron, and di-n,-butyl-(phenylamlac)-boron.
The reaction rate of aniline with the eaters inoreases in
the series of the asters of boric acid in accordance with
the gradation scheme boric acid eater 4 eater of phanyl boric
acid < eater of diphanyl boric acid. There are 2 figures,
1 table, and 12 references, 7 of which are Soviet.
ASSOCIATION; Institut organichesko~r khimii Akademii nauk SSSR
(Institute of Organic Chemistry of the Academy of Sciences,
USSR)
SUBMITTED: July 10, 1958
Card 3/3

5(5) SOV/79-29-9-68/76
-WTHORS: Mikhaylov B. M. Shchegoleva, T. A.
- 7~~~~
TITLE: Organoboron Compounds. XLVI. Dialkyl Boric Acids and Their
Derivatives
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Ur 9, pp 3130-3135
(USSR)
ABSTRACT: Alkylborates may serve for the synthesis of symmetrical and
unsymmetrical dialkyl borates. The butyl eaters of di-n,-butyl-
and n~propyl-n,-butyl boric acid were synthesized by reaction
of n,-butyl lithium or n4-propyl lithium with the nbutyl eater
of n,-butyl boric acid (Ref 11). Based on this method nbutyl-
ethyl-n,butyl borate and n,butyl-ethyl-npropyl borate were
obtained here according to the scheme:
RB(OC4H9)2 + C2H5Li ~, C2H5RBOU4H9 + C4H9OM,
where R - C 4H9, n.-C3H7* The synthesis of dialkyl boratea
on the basis of alkyl borates can also be practiced with
organo-magnesium compounds. Thus, a 45% yield of n,-butyl-di-
n.-propyl borate was obtained by reaction of n.-propyl mag-
Card r3 nesium bromide with n.-butyl-n.-propyl borate:

SOV/79-29-9-68/76
Organoboron Compounds. XLVI. Dialkyl Boric Acids and Their Derivatives
n.-C3H7B(OC 4H9)2 + n.-C3H7MgBr 0 (n.-C3H7)2BOC 4H9* The
dialkyl boric acids resulted from saponification of dialkyl
borates. The stability of dialkyl borates to hydrolyzing
agents is conditioned by the nature of the arrangement
of esters(for examples see references 8, 10). In this regard,
n.-butyl dialkyl borates are much more stable than glycol
esters (Refs 12, 13). The reaction of n.-butyl-di-n.-butyl
borate with a 10% caustic soda solution with subsequent
acidification is shown by scheme 1. Butyl alcohol is also
completely eliminated together with water in the concentration
of a salt solution (1) gently izeated and distilled in vacuum.
The crystalline residue is a sodium salt of di-n.-butylborenium
acid (II) in analytically pure state. The reaction process
of the formation of salt (II) in explained by scheme (2).
Di-n.-butyl boric acid (Scheme 5) results from acidification
of salt (II) after an intermediate stage of acid (7). Di-n.-
propyl boric acid and n.-propyl-n.-butyl boric acid are
colorless liquids tending to pass over into the corresponding
Card 213 anhydrides when they are heated. There are 14 references,

SOV/79-29-9-68/'76
Organoboron Compounds. XLVI. Dialkyl Boric Acids and Their Derivativea
4 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii Akademll nauk SSSR
(Institute of Organic Chemlstry of the Academy of Sciences,
USSR)
SUBMITTED: July 10, 1958
Card 3/3

5(2,5) SOV/2o-126-3-32/69
AUTHORSs Mikhaylov, B. M., Vaver, V. A., Bubnov, Yu. 11.
TITLEi Organoboron Compounds (Bororganicheakiye sayedineniya). Reactions
Between Boron Trialkyls and Compounds Containing Mobile Hydro-
gen (Reaktaii bortrialkilov s soyedineniyami, soderzhashchimi
podvizhnyy vodorod)
PERIODICALt Doklady Akademii nauk SSSR, 1959, Vol 126, Nr 3,
pp 575 - 578 (USSR)
ABSTRACTs The ability of aliphatic boron compounds to undergo the reactions
mentioned in the subtitle is very little investigated (Refs 1-6).
Triallyl boron possesses, however, an extraordinary sensitivity
to the reagents mentioned in the subtitle. It reacts with water,
alcohols and amines, even at room temperature. One or two allyl
radicals are replaced by corresponding groups. For these reasons,
the subject mentioned in the subtitle was of considerable inter-
est. The influence of the nature of initial substances on the
rupturing process of the boron-carbon compound could be
established. The authors studied the reactions between tri-n-
propyl-, tri-isopropyl-tri-n-butyl, tri-isobutyl- and tri-iso-
Card 1/3 amyl-boron on one hand, and water, alcohol, phenol, amines and

Organoboron Compounds. Reactions Between Boron Trialkyls SOV/'2o-126-3-32/69
and Compounds Containing Mobile Hydrogen
mercaptans on the other hand. It has been found that higher
boron trialkylB react energetically with watsr at 160-170.
Dialkyl boric acids 'I) are formed which are isolated in the
distillation as acid anhydrides with yields of 65-71% (Tuble 1).
The reaction is accompanied by the formation of olefine hydro-
carbons and hydrogen as well as saturated hydrocarbons (see
Scheme). The occurring relative hydrocarbon- and hydrogen
quantities depend on the test conditions. Boron trialkyls re-
act under the same conditions with aliphatic alcohols or with
phenol. Thus, they form alkyl or phenyl ester of the dialkyl
boric acids (II) with yields of 65-80%, as well as saturated
and olefine hydrocarbons and hydrogen. These reactions, as well
as those of the aliphatic and aromatic amines (III), finally
thuse of the mercaptans (IV), proceed in stageit they run
through a stage of complex compounds of boron trialkyls and
oxygen-, nitrogen- and sulphur-addenda (V). These compounds
(V)(1) undurgo two kinds of trtinsformationst a) the complexes
decompose into saturated hydrocarbons and corresponding oWuDboroi,
compounds (VI)(2). It seems here that a proton is removed from
Card 2/3 the heterogeneously bound atom, and the alkyl group is split

Organoboron Compounds. Reactions Between Bo2on Trialkyls BOV/2o-126-3-32/69
and Compounds Containing Mobile Hydrogen
off as an anion from the boron atom. b) Olefine hydrocarbon
and hydrogen are eliminated and formed (VI) according to
scheme (3). This process is most distinctly marked at the
interaction of the boron trialkyls with water, alcohob and
amines. The transformation of complexes (V) according to scheme
(3) is also possible w.th the formation of dialkyl boranes (VII)
which then separate a h.)drogen molecule. The above reactions are
simple and easy methods of producing the mentioned compounds.
There are 1 table and 10 references, 2 of which are Soviet.
ASSOCIATIONs Institut organicheskoy khimii im. N. D. Zelinskogo Akademii nauk
SSSR (Institute of Organic Chemistry imeni N. D. Zelinskiy
of the Academy of Sciences, USSR)
PRESEFTED. February 9, 1959, by B. A. Kazanskiy, Academician
SUBMITTEDs February 9, 1959
Card 3/3

5(2,3) SOV/2o-127-3-25/71
ii-THORS3 Mikhaylov, B. M., Bubnov, Yu. B.
TITLEt Dialkylthioboric Acids and Borocyandialkyls
PERIODIC&Lt Doklady Akademii nauk SSSR, 1959, Vol 127, Nr 3,
Pp 571 - 574 (USSR)
ABSTRACTt The esters of the acids mentioned in the title which the
authors developed by the influence of sulphur (Ref 1) or
n-butyl-mercaptan (Ref 2) on borotrialkyls, are very reactive.
Their reactivity exceeds that of their oxygen analogues. In
the course of further investigations it was proved that thio-
esters not only react with amines, but also with H 25 and HCN.
If thioester, heated to 14o-18o 0 permeates H2S/the acids
mentioned in the title andmercaptan will develop and can be
distilled according to theiL development. This is the way
the authors produced di-n-butyl-, di-n-propyl- and di-isoamyl-
thioboric acid from the n-butyl esters of the mentioned acids.
These are the first representatives of this type of organic
boric compounds. The properties and further transformations
Card 1j'3 of thio acids are descri-,Pd. N-butyl-esters of the acids

Lialkylthioboric Acids and Borocyandialicyla ScV-,2o-127-!-25/ /."I
mentioned in the title, react with HCN at low temperstjre
or with slight heating, and prodice the alk,71s (111, ~Lentioned
in the title. They are nitriles of unknown dialkyl-borin-
carboxylic acids. If the ethereal solutions of ri-bitylestcr
of Di-n-blityl-boric acid is mixed with HCN, heating occars.
A jellied precipitation develops which at first is colorless,
This indicates the formation of' complex compounds (11) ir. 1~he
first stage of the reaction. They soon change again Fr,c, Ole
cryoscopic molecular weignt, determined by means of benL~-.tl,
one can see that they are associated up to a certain Pxtent
A description is given of the physical prop-rties of the above
mentioned substances produced in this connection. Borocyqndi-
alkyls react with alcohols, if heated. At the same time estors
of dialkylthioboric acids and HCN develop. Crystalline ccmplex
compounds (IV), inconstant if exposed to air, at~velDp undi-r
the inflience of amines on the mentioned radicals Finally
the authors mention the known cyanogen derivatives of the
quadrivalent negative boron (Ref 4) and denote that the boro-
cyandialkyls, as well as their complex compounds, together
with amines, are the first representatives of the complex
Card 2/3 organic compounds of trivalent boron, containing a cyanogen

Dialkylthioboric Acids and Borocyandialkyls SOV/2o-127-5-25/71
group. There are 5 references, 5 of which art Soviet.
kSSOCIkTIONi Institut organicheakoy khimii im. N. D. Zelinskogo kkademii
nauk SSSR (Institute of Organic Chemistry imeni N. D. Zelins-
kiy of the Academy of Sciences, USSR)
PRESENTED: April 3, 1959, by B. A. Kazanskiy, Academician
SUBMIKED3 March 51, 1959
Card 3/3

5 (2, SOV/20-17-5-25/58
AUTMORSt Mikhaylov, B. M., Kozminnkaya, T. K., D-dot-jV, ::. S.,Do!-.khov, V. A.

TITLE. EE:~Prn of Cr~anot!~iobo,`c A--ids -~z_! Sc,,mr -,f 7h(,~ r ~rrinof-nat! n,;

?7-21(-DICAL: 1 2 - f
D,) k I ady Ah ado m i i nauk SS SR, 1 ')'7 -t 7~-, 1 7, :'r 5, 1,1: 2
( U Ssa)
AB S7 U C T S i n tl.( c- z -.,3o a 1
to Ine Very .1" ay 'it, I b~-tl f", ),4- n x n F;
C,r Various cor;.iourl,~n tl..(' alit'horr, ;.erp .r.
tfle production of t1.(-- aci,ls mentioned in the title and in tl,eir
behaviour. The known aliphatic monosubstituted and the aromatic
substituted esters of the thioboric acids are enumerated
(Refs 3-5) and their prrdict!-)n j,-,e,h,,dP, arf~ :.rji-,tiine~'A. 7h-
authors found t'-at ji_lu,it.~,j f
acids (1`,ef 1) ai-,j -Y. `Uu it, tlr.
ELIkyl lic'Inril,'S -1111
. By the sar.,e ester -,f the APnyll
fsee Scheme
i
,
%
thioboric acid (II) aas Diph,_-.,:y1 1,cron ,hlorfl~,- trA
di-01- -naphtlnyl -boron r-Lct in oimil,tr ,-1.Y sith n-butyl
mercaptan and fo--m ri-butyl e7~t--rE- r)f -Ii,,henyl thi,)Itoric acil
Card 1/3 (Ill. Ar = C 6H,'j and of Ji-c~,-rtaj:h thyl thioboric rcid

Est~ars of Organothioboric Acids and Some of SO 1.7/20-127-5 -251/56
Their Transformations
(Ill. Ar = c6-C 10 117). All esters produced are hijhly reactive.
This permits their transformation into other orEanoboric
compounds. By the action of ethvlene diamine the mentioned esters
are smoothly transformed into cyclic compounds, under "he
separation of n-butyl-mercaptan i.e. into 2-allcyl~2-boron-l,~-
diazolidine (IV). in the action of ammonia on the eoters of
alkyl- and aryl thioboric acids at low temperatures thr, trio
latter vrere traiisformed into the correspondirg 'Uoron trialk,~l-
and boron triaryl borazoles ~V). The rea-~tion between the ester
and the phenyl thioboric acid and diethyl &mine takes place in
one direction under the formation of phenyl-di(diethyl amino)boron
with a yield of 80%.1 whereas the amino compound (VI) is produced
from the phenyl boron di-,hloride only in a 1 ep yield (21ef 0).
Under the action of n-butyl eater of diphenyl thioboric acid
is transformed into diphenyl butyl amino boron (VII) in the
action of n-butyl amine in a 800% yield. The esters of
Card 2/3

Es'~-rs of Orcanothioboric Acids and Sorre -,f %V/20-1 27-5- ?5 /5P
Their Transformations
diphenyl thioboric and
ammonia at low temperatures.
boron (V111. Ar = C 6H5
amino-boror (VIII. Ar
5 of which are Soviet.
di-oe--t-iil,htliyl-tl-,iob(iric acid react with
In this connection diphenyl qui!-,:
see 7,che-ne) are formed )r di-Oc-1,apht'hil-
= OC-~,' 110 ii7). Ther, rirk-- 9 r~ferercca,
ASSOCIATION: Institut organicheskoy '-hi:1i 1,.D. Akadei~ii, r~au?
SSSR (Institute of Organlr.- -hemistry imeni 11, D. Zel~ ns',-,iy -)' the
Academy of Sciences, USS.'~)
PRESENTED: April 209 1959t by B. A. Kazans-iy,, k-.ad-mi-~ian
STTBMI 4'TED: April 10, 1959
Card 3/3

%100
AUTHORSa Mikh B. M*, Vaver, V. A.
2, =_
TITLEs
-
AOrganoboron Compounds- 56.
From Metaborates and Their
Acid Eaters e\
81554
S/062/60/000/05/OVOr~-'
B004/BO66
Synthesis of Trlalkylborone~
Conversion Into Dialkyl Boric
PERIODICALs Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh
nauk, 1960, No. 5, PP- 852-856
TRXTs A thorough investigation of the reaction of trimeric metaborate
with Grignard reagent in vacuo at low temperature and in the presence of
water excess revealed that the formation of dialkyl boric acid eaters
takes place via the intermediate stage of trialkylborons. At 9 - 9.5 M
Grignard reagent 70 - 80~ trialkylboron was obtained, i.e.% triisopropyl-
boron, tri-n-butylboron, and triisoamylboron. To check the assumption
that the eaters of the dialkyl boric acids are formed only by reaction
of trialkylborons with alcohol, the afore-mentioned trialkylborons wero
allowed to react with cyclohexyl-, aec.-octyl- and isoamyl alcohol, and
the follnwing compounds were obtain*ds eec.-octyl ester of the di-iijo
rnr4 1/~

81554
Organoboron Compounds- 56. Synthesis of Trialkyl- S/o62/60/000/05/0';/On8
borons From Metaborates and Their Conversion B000066
Into Dialkyl Boric Acid Esters
propyl boric acid, cyclohexyl aster of the diisopropyl boric acid, iLjC'
amyl ester of the dl-n-butyl boric acid, phenyl eater of the diisoamyl
boric acid. The data of these compounds are given in a table. The authore
discuss the course of the reaction between trialkylborons and alcohols
and give the following reaction equationst
R B + R I OH R B,..O"H , (Formation of a complex compound (1)). This com-
3 3 ~R ,H
pound decomposes according to equation MI R 3B4-0-, RI ----~R2BORI + RE, or
reacts according to equation (2) to form the complex (II)s
R Bt-O,' H -) R B40"H , + olefin. The complex (II) decomposes according
3 R9 2 R O/h
to equation (3), It 2Mir \R1 )R 2BORI + H2- The rate of the reactions (1,
and (2) - (3) d9pende on the nature of the trialkylboron and alcohol
applied. In the case of eec.-octyl alcohol and triioopropylboron the
ratio of the two reaction rates is 1 j 2.5. The reaction with cyclo.-
hexanol takes place according to equations (2) and (3), whereas in th-
reection -f tri-n-butylboron with iaoamyl alcohol both reL-ctYvL ~r-
Card 2/3

81554
Organoboron Compounds. 96, Symthesis of Trial-crl- S/o62/6o/000/05/0x/r,-
borons From Metaborates and Their Conversion B004/BO66
Into Dialkyl Boric Acid Esters
with equal rate. As may be seen from the preparation of the ph*nyl ester
(at 170 - 1600C), the reaction is possible also with phenols. There are
1 table and 6 referencess 4 Soviet, 2 German, and 2 American.
ASSOCIATIONs Institut organicheskoy khimii im. N. D. Zelinakogo Akaderril-
nauk SSSR (Institute of Organic Chemistry imeni N. D.
Z*linakiy of GO Academy of Sciences# USSR)
SUBMITTEDs Novembftr 3, 1958
Card 3/3

PATARDY, L.B.
;I .. Cyclization of athoxyfarnesenic acid* Izv-AN SSSR Otd.ichin.
nauk no-5;935-936 Ky 160. (MIRA 13:6)
1. Iastitut organicheskW khimii im. N.D. Zelinskogo Akademli
nauk SSSRs
(Tarnesenic acid) (Cyclization)

MLKHATWV, B.H.; SAVEL'YEVA. I.S.
Structure of the bromide GjOHjjBr, formed when bromine reacts
with 2-phonyl-2-butanol or 2-phanyl-2-butene. Isv.Al SSMLOtd.
khim.nauk. no.6:1049-1052 Tl 160. (M" 13:7)
1. Iastitut organicheakoy khlmll Lmeni N.D.Zelinakogo
Akademil nauk SSSR.
(Butene) (Butanol)

s/o62 '6o/Goo/007/0', '~/O' X-X
B0047BO64
AUTHORS: Mikhaylov, B. M_ and Ter-bark.syan, G S.
TITLE: Polyene Compounds. Communication I' Asymmetr,.cal
1,6-Diaryl-substituted Hexatrienes 1,3,5
PERIODICAL:Izvestiya Akademii nauk SSSR Otdpleniye khim,-cheskikh
nauk, 1960, No 7, pp 1267 - 1271
TEXT: In a previous paper the authors have described a simple
method of synthesizing 5-phenyl pentadieri-2,4-al-'. from the diacetal
of cinnamic acidiland vinyl ethyl etherl Thus, this aldehyde became
easily accessible to various synt I especial'y to the synthpsis
of asymmetrical 1,6-disubstituted hexatriene-1,',1,') der:.vat4ves In
the present paper, the authors report on the syntheses carried out
with 5-phenyl pentadien-2,4-al-- ') 1,6-dipherq', hexatriene-.5.') 'kA)
a) by means of the Grignard reagent obtaincd from magnesiam ar.J
benzyl chloride The reaction is carried out in absolute cther
(yield: 26 Al b) with benzyl sodium in toluene (yield: ',! '%)I
Card '13

Polyene Compounds Communication 1. 3/'062/60/000/007/0-3/01-(/'XX
Asymmetrical 1,6-Diaryi-subst-,tuted .9004//BO64
Hexatripnes-1,3,5
c) with phenyl a::eli:: acid in acetanhydride .n thp Fresencz- of 'ilharg-
ani boiling in nitrogen atmospher,- y-,ld: 34 '% 2) :-pheny-.-6
(a-naphthyl)-hexatriene-'.3 '~ (B) with a-naphthy' aetic R-id ,r.
aceta.'dehyde and '-n the presence of :1tha-ge; y eli: 2C 4% Contrary
to A, this compound luminesse3 strongly both -,n crystall,.zpd an'.
dissolved state 3) 1-phenyl-6-(g-phenanthryl)-hexatriene--,3 ~ (C)
by u-,eF-.-3 of the Grignazi reagAnt from Mg and 0-:h'.c:--) methy!
phens.r.threne in c-ther, Thi8 :cmpound 4) :-pheny-
hydroxy 6-(p-b-'phenyl)-h,~xadipne-1.5 (D) by means ~f thp Grignar!
reagent from Mg and 4-pheny! benzy' '7hloride in abscl-te ether
5) 1 pheny!-E-(p-bipheryl)-hcxatr4.ene-',3,~) (E) by boiling cf D -~n
glacial acetic acid 6) I-phenyl-6-(2 pyrid 1-h~xatriene-',3 '~ F)
with a-ploolyl-lithium in absolute ether 7~ 1 pheny1-5 hydr.-x'y-6
(2 quinolyl) hexadiene-2.4 (G) with 4u-inaldyl-lithum -.ri Pth,,,.-
8) ',-Phenyl-6-(2-quinolyl)-hexatriene 1,3 ~) H) by bc-,Iing ~f " -n
acptic acid. Thp introduct.,-n of hetervcyc'.,.z substi-i"n-,3 (E ard G)
leads to a weaker lumine5senc~ In a lat-r pap,r th- a;;th,:7-s w.:'
repcrt on the opti-al properti~,s cf these -,ompl-,inds
Card 2/3

Polyene Compounds, Communication
,/60/000 '00-/C - 3/0
Asymmetrica' ',6-Diaryl-substitutil D004/BO64
Hexatrienps-1.3,5
There are 9 references: 3 Soviet , I US and ~ Swiss
ASSOCIATION: Institut organicheskoy khlmii im N D Zelinskogo
Akademli nauk SSSR
(Institute of Organic Chemistry imeni N D ZelInsk:y
of the Academy of Sciences USSR)
SUBMITTED: December 27, .0~8
Card 3/3

3106 0/000/07/07/007
BO I 5PBOV54
AUTHORS: Mikhaylov, B. M., Shchegoleva, T. A., Blokhina, A. N.
TITLE: Reaction of Tetra-n-butyl Mercapto Diborane With
ULsaturated Compounds .I
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1960, No. 7, PP. 1307-1309
TEXT: The olefin hydrocarbons (hexene-1, octene-1, styrene) react with
tetra-n-butyl mercapto diborane at 70-800C in the preseme of pyridine
under formation of the n-butyl eaters of alkyl thioboric acids. The
reaction between tetra-n-butyl mercapto diborane and propylene or iso-
butylene proceeds in a complicated way. On heating tetra-n-butyl mercapto
diboraneo;ith propylene in the presence of pyridine in an autoclave
at 70-80 and 5-15 atm, the n-butyl eater of n-propyl thioboric acid
as well as the n-butyl eater of di-n-propyl thioboric acid and tri-n-
butyl thioborate are formed. Tetra-n-butyl mercapto diboraL, reacts
with isobutylene in a similar way; a mixture consisting of the eaters of
isobutyl thioborio- and diiaobutyl thioborio acid as well as tri-n-butyl
Card 1/2 ile

82103
Reaction of Tetra-n-butyl Mercapto Diborane With S/06 CO/000/07,107/007
Unsaturated Compounds BC15YB054
thioborate are formed. The formation of the eaters of dialkyl thioboric
acids and of thioborate is explained by the fact that tetra-n-butyl
mercapto diborane symmetrizes to thioborate and di-n-butyl mercapto di-
borane, and the latter reacts with the olefins under formation of the
corresponding eaters of dialkyl thiobario acids. There are 3 Soviet
references.
ASSOCIATION: Institut organicheekoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR
(Institute of Organic Chemistu imeni N. D. Zelinskiy of
the Academy of Sciences, USS
SUBMITTED: December 24, 1959
Card 2/2

S/062/60/000/008/017/033/xx
BO13/BO55
AUTHOR:
TITLE: Covalent Carbon Radii and the Question of Conjugation
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdsleniye khimioheskikh nauk,
1960, No. 8, pp. 1379-1386
TEM In the present paper the author deals with the concept of resonance
and the role of carbon orbital hybridization in the shortening of inter-
atomio distances, a question of great interest in theoretical organic
chemistry~ The considerable number of interatomic distances determined
precisely up to the present enabled the present investigation* Exact
measurements of interatomic distances were possible due to the develop-
ment of microwave spectroscopy. A review of th*published experimental
data showed that the covalent carbon radii in th~BP2 and sp states are
0-73 and 0*69 A.reepectively. It was shown that hyperconjugation of the
first order (a, % conjugation) does not exist. The shortening of a single
oarbon-carbon bond adjacent to a multiple bond is not due to the electron
shift assumed in the hyperconjugation mechanism (resonance), but to an
Card 1/2

Covalent Carbon Radii and the Question of 3/062/60/000/008/017/033/XX
Conjugation BO13/BO55
orbital effect, i.e., a contraction of the covalent carbon radii due to
an increase in bonding 9 orbitals. It was also found that in molecules
with alternating multiple bonds a n-olootron shift, and thus an equaliza-
tion of bond lengths, does not take place. The mosomerio (oonjugation)
effect (atatic effect of i,n conjugation) postulated by the concept of
r6sonanoo does not occur in this typo of molecule. The contraction of
single bonds in molecules with alternating multiple bonds is due to the
orbital effect. All data given or* *aktn from publications. Mention is
made of M. F. Mamotenko, V. M. Tatovskiy, M. I. Batuyev. There are
1 figure, 2 tables, and 30 references: 5 Soviet, 17 US, 4 British, 2
Belgian, I Canadian, and I Danish.
ASSOCIATIONi Institut organiohaskoy khimii Im. ff. D. Zolinskogo Akadsmii
nauk 5SSR (Institute of Organic Ch:mistry imeni H. D.
Zolirtskiy of the Academy of Sciono a USSR)
SUBMITTED: Maroh 6, 1959
Card 2/2

871,20-

'
,71,
12
123(6
,
S "0
1
3

D
7 O ,
220q. 2"
0(4
BO 1
AUTEORSt Mikhaylov, B. M. -ind Fi-J rl-,v, N. S
TITLE: Organoboron Comp(.1,ndzi C ommuni-hti,3n 18 Thp Effe- r-)f
Amines and Ammonia Upon Diaryl Boron Chlcrides
PERIODICAL: Izvestiya A kademii ra-jk. SSSR. Ollieleniy- k~
nauk, 1960, No 9, pp
TEXT: The authors investigated ore-anot:cron crimpound3 ani --r"
amines and ammonia upon diaryl bcron chlorides Ani:lnp, 'he prmHly
aromatic amine, reacts with diphenyl boron chloriI6 in thf- same manner an
secondary alophatic amines, and forms diphenyl phenyl amine boron a*. r-1-.n
temperature. The aromatic radical bound to bcron exerts also a string
influence upon the react'~vity of diary. bcron -hl-,ril-s Di- CK -naphthyl
boron chloride was found to be converted intr, c--)rre-sponeii ng N-subs t 4 1 uted
derivatives of di-o(-naphthyl am1ne borrn both under the action of primary
aliphatic and aromatic amines, and secondary aliphatic aminea at room
temperature. Thus, the following compounds were obtained: li-,Dl naph*hyl
methyl amine boron, di--o(-naphthyl isobutyl arnine brron. dl o( naphthyl
Card 1/3

87120
- j
Organoboron Compounds. Communicati-,r. ": Tt:~- 3 '06 2 '6 /C
Effect of Amines and Am-onla 7pon Diaryl B~7r')r. BO,',z//BO64
Chlorides
phenyl ami ne bo ron, and d i na p k. t, hy I I i P t hy f r TY-f- r
diphenyl boron chloride and di
differs compleLely. When bubbling ammonia at "aw teMpe.-atUr-e 'ILr'-~t-~.
benzene solution of di-cg-naphthyl toron chloride, 11-u-naphthy. aw,'rr-
forms readily. Diphenyl boron chloride forms a qtable complex with amm(r..-~
(Ref. 2). A complete analysis showed that 'it is the diammoniate of -ii-
phenyl boron chloride, which probably has a heteropolar structure. Tho
ammonium salt of diphenyl boreni,im acidt '(C6H5)2B(OH)2i 1qH4' formg durinv,
the hydrolysis of this complex N-substituted derivatives of diphc-nyl amln-~-
boron and of di-o4-naphthyl amine borcn xhiblt a dfferent 3t~ibility I
water. The stability depends bcth on the nature of the aromatic radicdIs
bound to the boron atom and on the character of thr, radicals in the amin-
group. Diphenyl phenyl amine boron and di o-naphthy! phPny! amin4-
are easily hydrolyzed by atmospheric humidity. wLile di-o( nafh~yl J:H*hy!
amine boron does not even change wher h(--Ated with water at '00 C f, r ' h
Ii-cA-naphthyl amine boron, di--LA-naph+hyl mcthyl am.,nP boron, anl (11 0~
-.qphthyl isobutyl amine boron do not changt- under the actl(,n rf whter at
.ard 2,'3

Organoboron Compounds. C,~mmu!iiciit 11)n T h-
Effect of Aminen and Ammonia T~j,- rj
Chlorides
73 f) Z
"Br) 4
room temperature for ont, hour; tt,-y v a-, r
1000C under the formation of the respe~,tlve amin;, tnd 'hf, di--/-napt.'~.Y'
boric acid. The latter decomposes into naphth~tllenf, fini --narhthyl ~or-.-
acid. The authors think that the compounds i~re mr-i-H stable to water !han
hexamethyl borazole which is hydrolized with water q' r-,,ir, t0mperFtfurf~.
Thus, the authors conclude that the relative stability of horaz-~'le and i-,
derivatives to hydrolizing agentq is not only chara-teristic of cy,71ic
compounds with boron - nitroger t-.-nds. b,-~t al.-3 of scme nitr,;,,er -ompounds
or boron with an open rhiir. Thor,, Fir- zj Z ) 'I ~ ~ ~ * t 1. 1 ' ~, P - M 'I "
ASSOCIATION: Inntitut ortnn1cho.-;k,,y khimii ir. M 1) Zelir~ikqo- Ak,ti-rn.
n .,A u k.13 '~ S F r. s t i , ) I , -, F a n C 7 r J M" n ~ 'I D
Z e I k 2 t h,-- 1,
S U BM I TT E D: Ma r
Card 3/3

S /0 6 2 '63 /', ~ --~''_ ' ', ,
B0271/BO64
AUTRORS: B and Kiselev, V. G.
TITLE: Radiation-chemical Transformations of Organic Substances.
Communication 4. Oxidation of Ethylene by Oxygen Under the
Action of Fast Moving Electrons
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh
nauk, 1960, No. 9, pp. 1619-1628
TEXT: The authors studied the oxidation of ethylene by oxygen in the
gaseous phase under the action of a beam of fast moving electroas. The
following problems were clarified: effect of the radiation time, ratio of
the initial gases, temperature and material of the reaction vessel.
Experiments on the effect of the total dose upon the oxidation process
were carried out with ethylene - oxygen mixtures. The ratio was 1 : 1.
Further conditions: room temperature, Initial pressure equal to the
atmospheric pressure, the vessel - an aluminum chamber. The time of
radiation was between 5 and 45 minutes, the radiation doses were
0.2-1023 - 1.7- 1023 ev. Figs. 1-4 list the experimental results It is
Card 1/4

Radiation-chemical Transformations of Oreanic S/C)6 1
Substances. Communication 4. Oxidation of B023YB064
Ethylene by Oxygen Under the Action of Fast
Moving Electrons
shown that ethylene reacts quicker than oxygen at the menti)ned dones
The difference increases at a reduction of the total dose rhis phqnc-
menon may be explained by the fact that in the initial period of the
reaction, the acetylene and carbon monoxide yields increase due to the
catalytic effect of the chamber walls, Glycolaldehyde, formic acid,
carbon monoxide, acetylene, and organic peroxides (hydrogen peroxide
in a very low yield) are the chief products of oxidation. The formalle-
hyde yield is 0.15 molecules/ICG ev The dependence of the oxidation
process on the interrelation of the initial gases was inve~~tigrited in *K-
same chamber and under the same conditions. Time of exposuret 11 m1nites,
dose: 0-55 - 1023 ev- Figs 5-6 show that the reaction rate of ethylene
with oxygen strongly depends ,n the intprrelation of the gases in the
initial mixture. This dependence is great(jr in the case ~f ethyli~-n'~~ Thc,
experimental results showed that the redur*.on of tho~- ethylene contain'
in the initial mixture leads tc an almost complete x-:dati!Dn r~f e*?.vleL-
On the other hand an increase of 'he ~,thylene content increases '.~ -~r_
version of oxygen. An inverse !,,,pendPnco ~x!.,3ts n the radiatton- I I
Card 2/4

S,10~ I 1,~ /,-,c - f-, r , - - - -
Radiation-chemical Tranpform-aticrs cf Or,-arlc 2/t~/
Z-~Astances. Communication 4. Oxidation olp ?0231?'.C')4
Ethylene by Oxyger Under the Action of Fast
I
oving Electrons
M
yields. The following data show that at small concentrations, formic acid
and carbon monoxide are the chief reaction products. To study the effect
of the walls of the reaction vessels upon the ethylene oxidation under
the action of fast moving electrons, experiments were carried out in
steel-, and brass chambers. Table 1 giveo the experimental resulto. it can
be seen herefrom that the ethylene oxidation in glass-, san-i
aluminum chambers takes approximately the same course. A consid -ablr
decrease of the peroxide and glycolaldehyde yield and an ircrease f the
yield in higher acids, carbon monoxide, formaldehyde, and butylene was
noticed in the brass chamber. Brass acts upon the primary oxidation
products and changes the direction of the secondary reaction2. The tempcma-
ture effect upon the process of ethylene oxidation was studied in an
aluminum chamber on mixtures 10 in the temperature range of -40 - +900,
in a glass chamber the temperature range was -4p - +200, at an exposure
time of 15 minutes. Tables 2 and 3 give the results of these inve~.itra-
tiona. In general, the dependence of the ethylene oxidation under the
action of fast moving electrons on temperature is no' great. Finall:.,, 1he
Card 3/4

Radiation-chemical Transformations of Crganic S/062/6O/0CO/0C?/01'/C2!
Substances. Communication 4. Oxidation of B023/)BO64
Ethylene by Oxygen Under the Action of Fast
Yovinf- Electrons
authors suggest a reaction mechanism which bases on the formation and
further conversions of ethylene peroxide (see'Scheme). The authors thank
V. S. Bogdanov for his assistance in the research work. There are 8
figures, 3 tables, and 14 references: 5 Soviet, 5 us, 1 Czechoslovakian,
2 British, and 1 German.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR (Institute of Organic Chemistry imeni N. D.
Zelinskiy of the Academy of Sciences USSR)
SUBMITTED: March 2, 1959
C-SH4 - c4HA*
C,H+ C'H402
r'li'O' -- H001,C110
(:,H,O, 2HCOOH
q1_1401 C~11- 2CH,CHO
C,H~ +0, - 2CO + 2H,
Card 4/4 C2H4+ + 202 - 2C0 + 2H,0

8h859
BOI 5YBo64
AUTHORS: Mikhaylov, B. M. and Bubnov, Yu. N.
TITLE: Catalytic Effect of MercaptanesiUpon the Conversion of
Boron Trialkyl Under the Action of Ammonia, kmines,
and Alcohols I
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeieniye khimicheskikh
nauk, 1960, No. 10, pp. 1672 - 1873
TEXT: The smooth course of reaction between thioesters and ammonia :.l-
lows to synthesize any dialkyl (amino) boron compounds (R 2BNH2 ) from
boron trialkyls, with mercaptane being used in quanti~lies that cause
catalytic effects. On introducing ammonia into normal boron tributyl or
triisoamyl boron to which approximately 1/25 equivalent of normal butyl
mercaptane had been added, normal dibutyl (amino) boron and diisoamyl
(amino) boron were obtained in yields of 70-75%:
S/06 60/000/0!0/013/018
Card 1/3

84859
Catalytic Effect of Mercaptanee Upon the S1062.V601000101010131C)18
Conversion of Boron Trialkyls Under the B015/Bo64
Action of Ammonia, Amines, and Alcohols
R3B + RISH 0 R2~SRI + RH (R - n-C4H 9' i-C5Hii~ R, - n-C a H9)
1 41
R2BNH 2 + RISH i B 2BSR',NH3 The thioester formed by the first
reaction regenerates mercaptane when reacting with ammonia; subsequently
mercaptane reacts with boron trialkyl, and this process is repeated un-
til boron trialkyl is entirely consumed . Thus, it is also possible to
synthesize N-substituted dialkyl (amino) boron compounds and eaters of
dialkyl boric acids. By adding diethyl &mine ton-tripropyl boron (with
n-propyl mercaptane), n-dipropyl (diethyl amino) boron Is obtained in a
yield of 92%:
(n-C H ) B + (C H NH n-C3H7SH I (n-C H ) BN(C H + C H
3 7 3 2 02 2 3 7 2 2 5)2 3 8
The authors of the present paper state that in th synthesis of n-di-
butyl (amino) boron carried out by Wiberg et al. lef-3). Booth and
Kraus ( 'Ref-4), as well as Evers et al. (Ref,5). not this substance is
concerned, since the properties of n-dibutyl (amino) boron synthesized
Card 2/3

8059
Catalytic Effect of Mercaptanes Upon the S/06 60/000/010/013/0!8
Conversion of Boron Trialkyls Under the BO15YB064
Action of Ammonia, Amines, and Alcohols
by the authors were other than those given by the afore-mentioned re-
searchers. The difficultly accessible methyl esters R 2BOCH3 were ob-
tained by the reaction
n-C 3H7SH
(n-C3H7)3 B + CH3OH - 0 (n --C3H7)2 BOCH3+ C3H8 By heating the
mixture of n-dipropyl (amino) boron with dimethyl amine, it was possible
to synthesize n-d.ipropyl (diethyl amino) boron. The Individual syntheses
are described. There are 6 referpnces; 3 Soviet, 2 US, and ' German
ASSOCIATION: Institut organicheskoy khimil im. N D. Zelinskogo
Akademli nauk SSSR (Institute of Organic Chemistry ;meni--
N~ D. Zelinskiy of the Academy of Sciences US
SUBMITTED: March 1, 1960
Card 3/3

84861
S /06 2/6 o/ooo /o 1 o/o 1 5 /o, a
B01 5/Bo64
AUTHORS: Mikhaylov, B._M. and Bubnov, Yu,, N,_
TITLE: Chelatelkeetyl Aoetonates of Dialkyl Boric Acidsr~
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh
nauk, 1960, No. 1OP PP~ 1883 - 1885
TEXT: In continuation of previous papers, the present article deals
with the conversion of n-tripropyl- and tributyl boron, of the n-butyl
ester of n-dibutyl thioboric acid, and of the methyl ester of n-di-
propyl boric acid under the action of acety! acetone. Three methDds of
synthesizing dialkyl boric acid acetyl acetonates (II) are described.
0-C., CH3
R B CH (II)
2 K, O-C "I
ICH3
(R - n-C 3H7' n-C4H9)
Card 1/3

84861
Chelate Acetyl AcetonaLes of Dialkyl Boric S/06 6o/ooo/o,0/015/018
Acids BOI 5YBo64
After a short period of induction (apparently necessary to enolize
acetyl acetone and to form borenium acid), a vigorous exothermic reac
tion sets in, in the first stage of which the anion of borenium 6.(-'id
splits off the radical R in the form of an anion which, together with
a proton, forms a saturated hydrocarbon and is converted into acetonate
(II). The acetyl acetonate of n dibutyl boric acid was also obtained by
heating the n-butyl ester of n-dibutyl thioboric acid and acetyl ace-
tone. In the third method of synthesis, an esterification was carried
out by heating the mixture of the methyl ester of n-dipropyl boric a~ld
and acetyl acetone; thus, the acetyl acetonate of n-dipropyl boric a-id
was obtained. The resulting acetyl acetonates, golden-green. easily
mobile liquids, were stable in dry air, The spectrum of the a,:etyl ace-
tonate of n-dipropyl boric acid dissolved in M 4 is given in Fig.
and shows the bands of the C-C double bond and the complexly bound
carbonyl group of the chelate P dicarbonyl compounds, The spectra were
taken by B. V. Lopatin on an OK(-'4 (IKS-14) spectrophotometer, There
are 1 figure and 11 references. 5 Soviet, 2 German, and 4 British
Card 2/3

8061
Chelate Acetyl Acetonates of Dialkyl Boric s/o62/60/000/010/015/018
Acids B015/BO64
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo
Akademii nauk SSSR (Institute of Organic Chemistry
imeni N. D. Zelinskiy of the Academy of Sciences USSR)
SUBMITTEL: March 11, 1960
L'I
Card 3/3

L4 9 2- D
'ORS: Mikhaylov,
1T1-1r.VM+VPF
.IT~V Synthesis
?DIODICAL: Izvestiya
1)60, No.
86n.8
S/06216011000101 0/02 9/0 x 1 11XX
B004/BO60
B. M, and Ter-3arkisyan, G. S.
kwiran"M
of Mercaptals
Akademii nauk SSSR. Otdeleniye khimicheskik)i nauk,
10, pp. 1886-1887
'.,'i,XT: The re3ently much investigated reaction of aldehyde acetals with vinyl
ethers meets with difficulties in some cases, because of the complicated
chardcter of synthesis cf corresponding acetals. In the stud under -on-
y
the authors intended to simplify their task by using easily
RCH(SC 11 ) -
btainable mercaptals, 2 5 2- instead of acetals. The following re
action is described: A mixture of ethyl mercaptan with ZnCl 2 and Ila2SO4
i3 cooled down te 0 -20C, and aldehyde is added dropwise. The temperature
not exc,~ed 0 C. After being allowed to stand in a refrigerator 'or
h, the uji.cture is poured into 1(.,(j water, the separating oil ia f!X.
..dcti.d with ether, washed with 10% lye, and subsequently with water, dried
k,var Na so ~ni distilled in vacuum. Under these mill conditions, Jiet~:yl
-ard 112 2 4

Sy-rthes'-~ of Mercaptals
86728
3/062/60/000/01 31'0z~/o Zl,'XY
BO-04,,'BO~O
mercaptals of cinnamaldehyde, 5-phenyl pentadien-2,4-al,
citral, benzaldehyde, and furfurole were obtained in good
A report ia to follow concerning the condensation of these
a,p-unsaturated ethers. L. S. Povarov is mentioned. There
10 references: 5 Soviet, 2 US, 1 Japanese, arid 2 Swiss.
ASSOCIATION: Institut organicheskoy khimii im
nauk SSSR
(Institute of Organic Chemistry
Academy of Sciences USSR)
SU13MITTED: March 21, 1~60
citral, P-c '~Clo-
yields (',~.1-77-5%;
mercaptals with
are I table ani
N. D. Zelingkogo Akademi
imeni N. D. Zelinskiy of ti-le
Y
V
Card 212

ooTLY
3 '062/(~010,1
O/C 10/0 ~D,'j X
B004/7-9060
u2s: M i K h ay 1 o V 2 -J~--- 11 an JTer-Sarkisyan, S. S.
Condensation of Mercaptals With Vinyl Ethyl Ether
Izvestiya Akademii nauk SSSR. OtJeleniye khimichesKilt',. nauk,
1960, No. 10, pp. 1888-1891
TEXT: In a previous paper (Ref. 2), the authors synthesized liethyl mer-
ca:-t,,Als of benzaldehyde, cinnamaldehy(le, and P-cyclocitral. The article tinder
consideration deals with the condensation of these compounds %ith vinyl
ethyl ether. The reaction took place with merca,,-tal in the presence of BF,
-jtlaerUte or ZnCl2 solution in ethyl acetate as a catalyst, addition by
Jrops of vinyl ether w1thout allowing temperature to rige, mixing with ether,
and d ist 11 lation of the ethor extract in vacuum. The fol low ing achome I S
:~i ver; : _--OC H
-:(SC H5 + -,H - CHOC H --P RCH~SC H )CH CH R "I);
2 2 2 5 2 5 2 1'-- SC H,
10- CTI= CH- Cq~ H 3 2
~-trd 112 0--ZH 3 (111).

867V
llcndensation of blercaptals With Vinyl Ethyl Ether S/-062/60/O,)0 01")"'C"a"031
-9004/2-0(0
The pre~-~nce of the mercaptal group was proved by a sublImate 'Ref.
ing with glacial acetic acid effects the conversion of synthesized compounds
into unsaturatel aldehydes. Cinnamaldehyde was obtained from 1-ethoxy-1,3-
di-(ethyl mercapto)-3-phonyl propane (I), while 5-phenyl pentadien-2,4-al
was obtained from 1-ethoxy-1,3-di-(ettlyl mercapto)-5-phenyl pentene-4 (II).
Saponification of (I) in the presence of 2,4-dinitro phenyl hydrazone
(2,4 DNP11) gave 2,4-DUPH of 3-phenyl-3-othyl mercapto propanal, which, n.~i
boiling with alcoholic 11C1, was converted into 2,4-DNPH of cinnamaldehyde
The ethyl mercapto group, not the ethoxj group, is separated on further -- 11-~
action of (I) with vinyl ethyl ether to form 1,3-diethoxy-1,5-di-(ethyl me!-
capto)-5-phenyl pentane. The structure of this compound was proved a) ij
reaction with sublimate (proof of the mer'capto group); b) reaction alth
DNPH: formation of 2,4-DNPH of 5-phenyl-5-ethyl mogrcapto penten-2-al, whi(-h
was converted into 2,4-DNPH of 5-phenyl pentadien-2,4-al. There are I
and 7 references: 5 Soviet, I US, and 1 French.
ASSOCIATION: Institut organicheakoy khimii im. 11. D. Zelinskogo Akademi,.
nauk SSSR (Institute of Organic Chemistry imeni N. D. Zelinskij
of the Academy of Sciences USSR)
SUBMITTED: March 23, 1960
Card 212

HINHAYWV, B.H.; POTAROV, L.S.
- -
Reactions of 1,3-diozolanes withc~,Ilf-unsaturated ethers. 1xv. AN
SSSR Otd. Wm. nauk no.10:1903-1904 0 160. (MIRA 13:10)
1. Institut organicheakov khimii im. N.D. Zelinskogo Akademii nauk
SSSR.
(Dioxolane)

MIKHATWV, B-.,M..; 'IUTDRSXAYA. Y.B.
Action of ethyl marcaptan on trillylborine. Izv- Ali SSSIL.Otd.
khIm. nauk no.11:2068 N 160. (HIRA 13:11)
1. Institut orgunicheakoy khimii im.N.,J.Zelinakogo tN SSS"R.
(Borine) (Nthanethiol)

r
B 0 1 ri , 4
AUTHORSz M.ikhayl(:v, B. M. ari-j K(,zm-n:!kaya. T. K.
TITLE: Synthesis ~,f R Tr'.alkyl Ff--,n Allky: Tn-. ri
Estera
PERIODICAL: Izvestiya Akidemii na~-.k SSSR k! ~e~.
ra _i k N 12 p p 4 - - 2 24 Fi
TEXT~ The auth~,rs briefly report r.r. a ,3 t u .1 y r) f t h n
esters .~f alkyl thir,~bnri~ acids with ammon-E& The
r,~,om temperature to gJ.v" B-tria'kyl in t0-136~
f ra t reac I i c.~n s t age , -Ami nr t h' -es t t- r i -- f- rrred wh h I iv rn 1~ re,; -,,r'-qJ I
condenses to bcrazole. The ised n-b,ityl es+eri -f n-propyl and r, 1-ii~yl
thicbcric a(,' d were sync hesizol by thp act ion rf n b-,;!yl m; r--3L[ t -~r, tc~
ccrresponding alkyl bor-.r. ibrrmides (R,~f I ) . D-, -n - bi; t yl -s ! F- r - f I S
propyl thiob,,ric acid was obtained for the firs, time, als, by thf~ a-111-r
of n-butyl mercaptan on isoprr~pyl b,!rr)n d"brom4de- Thr- Iatler w,,.Tl
synthesized from lsoprrpyl hrri- arhylriJe, and hor~,n tribrnm.4de by ~1,;-
mr-*hr)d described in Ref ' B-trialkyl derivativ,45 of ta~razrje,
Card 112

Synthesis of B-Trialkyl B-',raz--les Fr--m S/'-)'
Alkyl Thiobor'c EstE-rs
B-+r4methyl boraz,:Ae (Rpf r.,! R r'alkyl 1- ',R.,f w-r-
formerly obtain,?d by hr-ating ~he r. I n g r- - r. I i K L 7 Ir r
In -in a u t - c I ave a' 51, 0 '- A 0' C A i1 ;- ~7 YV t , ~ , '. .-
-.rganohorcn compoundE n a dry nitr( k.7, n m 9 d i u m Thc-rr- rof-r~~!-. .-I
5 Scviet and 1 German,
ASSOCIATION: Ins*i*ut rgani-heskr -,- k r. : m T N. L Z,~ n ~~'K, gr A k
na-ik SSSR (Institu~,~ -f
ly .f thp A-,lv~ y -,f "SSR,
N, D, Zelnsk~
SUBMITTED- May r) f'O
Card 2/21

S/074/6O/C,2',)/C,0bj'CC I /t-Cl
B01 5/B054
AUTHOR: Mikhaylov, B. M.
TITLE: Borazol and Its Derivatives
P"MIODICAL: Uopekhi khimii, 1960, Vol. 2~, No. 81 pp. 972 - 994'
TEXT: The present article gives a complete survey of publications no
the chemistry of borazol with special consideration of periodicals of
1958 and 195). All essential m~!thods of synthesizing bordzol and it,~
derivatives are indicated and discussed. The article is divided int(,
three sections. The first section deals with the methods of aynthesj--,-,~
the borazol ring: 1) Synthesis from diborane and its alkyl derivativf-a,
2) synthesis from boron trialkylej 3) synthesis of borazol derivati--;~
by means of boron trichloridei 4) synthesis with the use of ammo.iivf
salts and lithium boron hydride; 5) synthesis of borazol derivatives
means of N-substituted derivatives of amino boron dichloride; 6) sp-
theeis of borazol derivativea from alkyl- or aryl boron dichlorides;
7) synthesis from i-eubstituted derivatives of alkyl- or aryl (diainfl,
boronj 8) aynthesis from esters of aryl chloroboric acids; 9)
,ard 1/2

Borazol and Its Derivatives S/07 601029100810,,11(_,_'
BC1 5Y2054
from eaters of organothioboric acids; 10) synthesis from tetra-alkyl-
mercapto diboranes. The second section deals with transform%tions of
functional borazol derivatives: 1) Synthesis of borazol and Its deTivrj
tives from B-chloro derivatives of borazol; 2) synthesis of borazol
derivatives from its N-alkyl- and N-aryl-substituted derivatives. Th.~
second section also indicates the most important properties of boraZrj'
and its derivatives which allow conclusions to be drawn as to thp tran-
sition from one derivative to the other. At the end of the present
paper, the chemical and physical properties of borazol and its deriva-
tives are indicated (Tables 1-5), and discussed in the third section.
The following names are mentioned in the paper: A. F. Zhieach,
L. N. Kochneva, V. 1. Mikheyeva, V. Yu. hiarkina, T. V. Kostroma,
P. M. Aronovich, T. K. Kozminskaya, N. S. Fedotov, V. A. Dorokhov,
T. A. :~. cl,Q;,ci(~vn- 21-re are 5 tables and 71 references; 13 Scv!F--t
13 German, 3) JI: , !-.1 (. ritinh ,
ASSOCIATION: ln-t khiuii All SSSR im. N.D. Z,.~linsknjzu
(Institute of ~)rlanic Chemistry of the AS USSR imeni
Card 2/2

MIKHATWV, B.H.; TER-SARKISYAII, G.S.
Pol7ene compounds. Part 12; Ccndensation of 5-phen7l-2,4-pentadional
with arylacetic acids. Zhur.ob.khim. 30 no.8:2521-2524 Ag 160.
(KIU 13 - 8)
1. InBtitut organicheskoy khimii Akademii nauk SSSR.
(Acetic acid) (Pentadienal)