SCIENTIFIC ABSTRACT ARBUZOV, B.A. - ARBUZOV, B. A.

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• Publication Date: December 31, 1967
• Content Type: SCIENCEAB

ft-UZOV. 8.A. AcRdemician (Chem. Inst. 11n. A. Yp.
Arbuzov-# Kazan Affil. As US
_qR)
"MOthOds of Developing Organic Darivativos
organicheskikh proizvodnykh fosfora) Of Phosphorus" (Putl
razviti3la
Cbed$trY and Ilsell of organophosphoroul; compounds
(Whjujis j primenenive fogfrorganicheskikh sriYedneni-v
TIVAW of First Confe e, 8.io December 1955, Kazan,
PP4- pa lished by Kagm Affil. As USS11i 1957
117

A. V.; V.Ui10GP-4DQVA, V. L.; TGU~A---
U' %,nr1VWY T. G (Chair
o an c emistry and NII of Chemistry im. A. M. Butlerov of Kazan State
University im. V. I. Ullyanov-Lenin)
"Intermediate Products By the Arbuzov Rearrangement"
(Promezhutochnyye produkty
pri peregruppirovke Arbuzova)
Cher,dstry and Uses of Organaphosphorous Compounds
(Iatmiya i prineneniye fosfororganicheslu-1di srjjedneriy),
Trudy of First Conference, 8-10 December 3955, Kazan,
pp. Published by Kazan Affil. AS USSR, 1957
&X- 1-4-
Report discussed by: B.-Ya. Teytellbaum (Chem. Inst. im. Acad. A. Ye
Arbuzov, Kazan Aff.
AS USSR), M. I. Kabachnik (Inst. Elementary Organic Compounds AS
USSR~, and V. S.
Abramov (Kazan Chem. Technological Inst. lm. S. M. Kirov).
Fxperiments mentioned by
V. S. Abramov were conducted by A. I. Bollshakova.

ARBUZOV B. A.; VI;NCCFiAfjGVAy V. S. (Chem. ins,". it- il. I.I.
Butlerov. wiClier 4.1w Lnzan
Stat~-~'-1,iv-er'slt-.V Lm. V. I. Ullyanov-Lenin)
"Esters of Beta-Ketophosphinic Acids and Some of the Their
Properties" (Efiry
Beta-ketofosfinovykh kislot i nekotoryye ildi svoystva)
Chemistry and Uses of Organopbosphorous Campoundr.
(Khlmiya i primenenlye fosfororganicheskikh sayedneniy),
Trud~r of First Conference, 8-10 December 1955, Kazan,
pp. Pub.Ushed by Kazan Affil. AS USSR, 1957
jj~-/Wy
Report discussed by A. N. Pladovik (Chem. Inst. im. Acad. A. 'Ye.
Arbuzov, 'Kazan Affil.
AS USSR) and 14. 1. Kabachnik (Inst. Elem. Orgazt. Compounds AS
USSR, Moscow)

11 A
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iv

WRIMOT, N.N.; SRMGIN, A.G.; NUZHINq MoTs, prof., otv,
red.; NAZW.
K,T,, prof., ;ameetitell otv. red.; KASOANOTs.BeG.,
prof., red,;
AMZUZQY -I.A" a~adeinik, red.; ALITSOM, S.A.~-
. p prof., red.;
_AOV, N.A. red.; N A*Po, prof., red.; PISARIffe
j!V 9 p-rof-9 0
V.I.' prof.' red.; TIKHTINSKAYA, Ye,.I,'.,, prof'.,
red.; BARYSMKOV,
V.G.:-doto.: red.: KM~SNIXOVA, Ye.A., dots., red.;
KOLCBDV, N.VO*,
dots., red.; MMOZOV, D.G., dots., red.';'KHARITONOV,
A.P., dots.,
red.; TMIN, I.N., red.; SAKITOV, Yu.Tu., red.
[Investigations of wells dnd development of preventive
paraffin
control methods] Ionledovanie skavazhiny i razrabot~a
prevently-
nfth matodov"borlby s-parafinoim, K~zanl'195~. 108 pe
(Kazan.
Universitet. UcheMe zapiski,~ Vol. 127, ikoe'D.. (MIU
11:5)
1. Rekbor lazanskogo gosudarstve 'nnogo universitets,
(for Nazhin).
2. Prorektor po nauchnoy rabote Xazanskogo
gosudarstvennogo univir-
sitita (for Mar1mv )0L- 30 Frorektor po nchebnoy
rabote Kazanskogo
gosudarstvennogo universiteta (for Kashtanov)* 4.
Sekretar" part-
kom -razanskogo goondarstvennogo universiteta (for
Tudin).
(Oil wells) (Petroleum engineering)

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AUTHCRS:
Arbuzov B, A and Vinogradova, V. S. 62-1-8/21
TITLE:
Esters
of Beta-Ketophosphinic Acids (Beta-Ketophosphinates) Part 1.

Phosphonacetic Ester,, Phosphonacetu-ne and their Homologues (Efiry

beta-kBtofosfinovykh kislot, Soobshcheniye 1. Fosfonuksusnyy efir,

fosfonatseton i ikh gomologi)
PERIODICAL:
Izvestiya Akademii Nauk
SSSR, Otdoleniya Khimicheskikh Nauk, 1957,

No. 1. ppe 54-64
(U*S&S*R.)
ABSTRACT:
Date are presented on the synthesis of certain
substituted derivatives

of phosphonacetic ester, phosphonacetone and
its mathyl derivatives ard

the results obtained during the titration
of these compounds with bromine.

The three methods employed in the
synthesis of these compounds are : A,

reaction of
alpha-halogeno-carbonyl compounds with phosphorous acid

esters (the
A. Ye, Arbuzov regrouping); B, reaction of dialkylphosphites

with
alphs-halogeno-carborWl compounds (Michael's-Becker reaction);

and
C. alkylation of the metallic derivatives of beta-phosphoncarbonyl

compounds with alkyl halides. The constants and properties of the

compounds obtained by the three different methods were found to be

quite different. It was found that the amount of phosphoric ester
Card 113

62-1-.6/21
Esters of Beta-Ketophosphinic Acids (Beta-Katophosphinates) Part 1.
Phosphonacetic Ester, Phosphonacetone and their Homologues
obtainable depends upon the reaction temperature and nature of the
halide, high temperature aids the formation of katophosphinic acid
ester., lower temperature promotes formation of phosphoric ester.
The chloro-derivatives sometimes yield an unsatarated phosphoric
ester; the formation of unsaturated phosphoric acid esters explains
the abnormal case of unsaturation in the di-substituted compounds.
The enol content in the phosphonacetic and methylphosphonacetic
esters,
determined by the bromine titration method, is explained by the
presence
of hardly-separable small amounts of unsaturated phosphoric acid
ester.
Considerable enolization takes place in alkali media.
Card 2/3 Tables, graphs. There are 24 references, of which 10 are
Slavic.

62,.1-8/21
Esters of Beta-Ketophosphinic Acids (Beta-Ketophosphinates)
Part 1.
Phosphonacetic Ester, Phosphonacetone and their Homologms
ASSOCIATIDN: The Kazan' State University imeni V. 1.
Ullyanov-Lenin., Institute
of Chemistry imeni A. K. Butlerov.
PFMNTED BY:
SUBMr=: January 12., 1956
AVAILiMs Library of Oongress
Out 3/3

gg mm
g,~ ,,,i
rZq,

1. 44 20

e
T:
W.W.10 r1i

~ ~- 13u, Z C. V1~ , 4 ~ 30-8-8/37
AUTHOR: Arbuzov, B.A., Academician
TITLE: Th6 Annual Meeting of the British Society for Chemistry
((;odichnoye sobraniye Angliyskogo khimicheskogo obshchestva)
PERIODICAL: Vestnik Akademii Naulk SSSR, 1957, Vol. 27, Hr 7, PP-
57-59 (USSR)
ABSTRACTs By invitation of the above mentioned society the author
took
part in the annual meeting (9 - 12 April 1957) at Cambridge.
Three groups were at work. The themes worst "The Ethers of Phoav.
phoric Acid"; "The Reaction of Free Radicals in the Gaseous
State"I "Present-Day Notions of the Anorganic Chemistry of Nitro-
Cen". The theme "Ethers of Phosphoric Acid" was not just select-
ed by chance; the head of the symposium, Sir A.Todd, acquired
world-fame by hi,% work within the field of the synthesis of nu-
cleothydes. After an introductory address by Sii A. Todd, F.H.
Viestheimer (U.S.A.) spoke about the investigation of the solvo-
lysis of some phosphorus ethers. On this occasion he stressed
the fact that it is extremely easy to carry out the hydrolysis
of ethylene Glycole ether, which is t~a reason why the rapidity
of this reaction exceeds tl-j-- hydrolysis of dimethyl phosphorus
Card 1/2 ether by jo7 (107). In the USSR chemical research work
achieved

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0

ob
tiWl

OV, B.A.; BOGONOSTSEVA, N.P.
Synthesis of some phosphosulfides and phosphooulfones,
Zhur. ob,
khim. 27 no.9:2360-2362 S 157. (MIRA 3-1:3)
I.Xhimicheskiy institut pri Irazanskom
gosudarststvennom universitete*
(Chemistry, Organic--Synthesis)
(Stafides)
(Sulfones)

ARBUZOV, B.A.. akademik; FRINOVSKATA, V.A.
Me of some cf-pinene derivatives and their isomer~lxation.
Dokl. AN SSSR 112 no,3:427-429 Ja '57- (MIRA 10:4)
1. Nauchno-losladovatellskiy khtmicheaki3r Institut im.
A.M. Butlerova pri Kazanskom gosudarstvennom universitete im.
V.I. Ullyanova-Lenina.
(Pinene) (Isomerization)

LWHOR:
ARBUZOV,B.A., PUZHENKOVA,1-V- a-)-6-23/59
TITLE:
Interacti
between Phosphorus Ethers and Alkyl Halides Studied

by means of
Physical -Chemical Analysis. (Izucheni~~ vzaimodeyetviya

efiroy
foaforistoy kisloty s galoidnymi alkilami metodami fiziki-

khimicheskogo analiza, Russian)
PERIODICALt
Doklady Akedemii Wauk
SSSR, 1957, Vol 113, Nr 6, pp 1269-1271

(U.S.S.R.)
ABSTRACTi
The
rearrangement mechanism by L.Ye.ARBUZOV has already been

studied
since 50 years. According to his opinion the rearrangement

of
phosphites into ethers of the alkylphosphin acids are an inter-

mediate stage, on which occasion an intermediate product of the

phosphonium type develops. This is experimentally proved for

aromatic phosphites. According to one opinion such intermediate

products collapse immediately and automatically. Some
soientistst

however, maintain that the rearrangement in question
can occur

according to another mechanism without affixing the
alkyl halide

to the phosphite. Here results are described which
were obtained

on the occasion of the investigation of ARBUSOY's
rearrangement ly

mein& of the physical-chemical analysis method.
The main task was

to show the possibility as to how the diagram
composition-property

can be used for the study of the problem of
the formation of an

intermediate product. The interaction between
triethylphosphite
Card 1/2

AUTHOR
AMUZOV, B.A. I FUMMA, A. V. 20-1-24/64
TITLE
Me
Inves,zigation of the Re.-Orouping according to Aae,

ARBUZOV by
the Thermographio-Method.

(Izuel,aidye peregruppirovki A.YE).
Arbuzova metodom termograf ii. -

Russian).
PERIODICAL
Doklady
Akademii Nauk SSSR 1957, Vol 114, Nr 1, pp 89-929p

(U.S.S.R.)
ABSTRACT
Arbuzov, who discovered the re-grouping of phosphorus
ethers, as

well as of the ethers of alkil phosphine aoide under
the in-

fluence of galoid alkiles assumed that regrouping takes
place

by the formation of the intermediate product by the coupling

of the galoid alkile to the trivalent phosphorus. For aromatic

phosphites the formation of the intermediate product by

separation
was proved. For aliphatic phosphites a separation

of the
intermediate products is not possible (apparently be-

cause they
do not keep). The results obtained by ARBUZOT when

investigating
re-grouping by the thermographic method are des-

oribed. By this
method it is possible, without difficulties,

to prove the
development of processes occurring as a result

of liberation and
absorption of heat. In order to check the

possibilities offered by
the thermographio method thermograms
CARD 1/2

AUTHORS: Arbuzov, B. A., Khfsaatullina, A. G. 62-2-6/28
TITLEs On the Structure of the Resin Acids of Turpentine From
Pinus Pithyusa in Pinus Insignis (0 sostave smolyanykh
kislot zhivitsy pinus pithyusa y pinus in3ignis).
PERIODICAL: Izvestiya AN SSSR Otdeler-ir- Khir,,icheskikh Nauk,
1958, TIr 2,
pp. 166-173 (USSR).
ABSTRACT: Numerous researchers for many decades dealt with the
structure
of the above-mentioned resin acids and their elimination. The
investigation of these acids, however, meets with great
difficulties due to theireasy variability. The property of
these acids to form mixed crystals also renders the investi-
gation very difficult. After a number of successfully employ-
ed methods the discovery was made that a small quantity of
resin acids, separate from each other, exists in the sap of
various Coniferae. A new acid, palustric acid (reference 4)
is now added to the already discovered ones. As Garris (re-
ference 5) already proved, abietic acid is the primary acid.
The elaboration of the quantitative methods of the determin-
ation of individual resin acids of turpentine showed that
Card 1/2 individual resin acids which were eliminated from the sap
(in
I

On the Structure of the Resin Acids of Turpentine From 62-2-6128

Pinus Pithyusa
in Pinus Insignis.

very small quantities) constitute
an important part of this

sap. For this reason it was of interest to
find out how the

resin acids are composed in a quantitative and
qualitative

respect. The present paper gives the results of this
research.

Thus the composition of the above-mentioned resin acids of

turpentine of P. Pith.Yusa was investigated. This composition

of the
crystallized and dissolved part of the resin acids of

turpentine is
similar. They contain: laevopimaric acid 8%)

abietinic acid 35,740,
neoabietinic acid 8%, isodextropimaric

acid and others 15~fo
respotively. In P. insignis: The resin

acids of turptntine contain
laevopimaric acid 35~;, abietinic

acid 6,5%, neoabietinic acid 14%
and dextropimaric acid 24%-

There are 7 figures, 2 tables, and 12
references, 5 of which

are Slavic.
ASSOCIATION;
State University imeni
V.I. Ullyanov-Lenin, Kazan' (Kazanak -iy

gosudarstvenxiyy
universitet imeni V.I.. Ullyanova-Lenina).~-
SUBMITTED:
October 16,
1956
AVAILABLE:
Library of Congress
Card 2/2
1. Resin acids-Analysis

AUTHORS., Arbmuz enskiy, Sol/62-58-6-9/37
'~'~Xizpolozh
Ms A.
TITLE: The Esters of Ethyl-Phosphinic Acid and Some of Its
Transformations (Efiry etilfoafinistoy kisloty i ikh
nekotoryye prevrashcheniya) Communication B. Mixed
Anhydrides of Dialkyl-Phosp4brid Acid, Ethyl-Phosphinio
Acid, and Diethyl-Phosphinic Acid (Soobahcheniye 8.
Smeshannyya angidridy dialkilfosforistoy, etilfoafinistoy
i dietilfoofinistoy kislot)
PERIODICALt Izvestiya Akademii nauk SSSRp Otdeleniye
khimicheskikh nauki
1958, Nr 6, PP- 706-712 (USSR)
ABSTRACTs Kosolapov and Watson (Uotson) (Ref 1) were the first to
obtain anhydrides of di-n.-propylic and di-n.-butyl phosphinic
acid as a result of the action of the chlorine anhydride of
dialkyl phosphinic acid upon the esters of'this acid,.Later,
the same authors (Ref 2) obtained anhydrides of dimethyl-'
and adiethyl phosphinic acid. In the present paper the authors
describe the method of obtaining mixed anhydrides of the type
Card 1/f (Et )2 P - 0 - P (OH )2 (R=C2"5 I C3H7-n; C3H7- 1)4

The Esters of Ethyl-Phosphinic Acid and Some of Its
SOV/62-58-6-9/37
Transformations. Communication 8. Mixed Anhydrides
of Dialkyl-Phosphoric Acid, Ethyl-Phosphinic Acid,
and Diethyl-Phosphinic Acid.
(C H P - 0 - P -"'-'C25- Under the action of alkyl
2 2 '-,02H5
halides brought to bear upon the mixed anhydrides
-tetraalkylhalidephosphonium is formed. Under the action of
sulphur the mixed anhydrides combine only with a sulphur
atom (and sulphur combines with phosphorus which contains
2 ethyl radicals). There are 2 tables and 3 references#
ASSOCIATIONt Khimicheskiy institut im. A. Ye. Arbuzova,
Kazanskogo
filiala AN SSSR (Chemical Institute imeni A. Ye. Arbusav
Kaza4 Branch,AS USSR)
SUBMITTED: December 21, 1956
Card 2/6

50)
AUTHORS: Arb Zoroastrova, V. M. SOV/62-58-11-9/26
TITLE: 'Festers of Pho'sphoric and Thiophosphoric Acids
Containing
Heterocyclic Radicals (Efiry fosfornoy i tiofosfornoy kislot,
soderzhashchiye geterotsiklicheskiye radikaly)
Communication I. Compounds Containing Pyrimidine and Imido-
methyl Uracil Radicals (Soobshcheniye 1. Soyedineniya s
pirimidinov-ym i imidometiluratsilovym radikalami)
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheskikh nauk,
1958, Nr 11, pp 1331-1339 (USSR)
ABSTRACT: In the present paper the authors'synthesized a
number of
eaters of the phosphoric and thiophosphoric acids with
pyrimidine and imidouracil radicals. The physical properties
of~the obtained products are given (Table 1). Compounds Nr 1
and 2 are high-boiling, viscous, oily liquids easily soluble
in the ordinary organic solvents and difficultly soluble in
water. Compound Nr 2 was described by Shvetsova-Shilovskaya,
Mellnikov, and Gral33v (Ref 2). Compound Nr 4 was obtained in
liquid as well as also in crystalline state. The other com-
pounds containing the pyrimidine radical, are low-melting
Card 1/3 solids. Products Nr 3, 49- 5 were obtained in good
yields from

Esters of Phosphoric and Thiophosphoric Acids
SOV/62-56-11-9/26
Containing Heterocyclic Radicals.
Communication I. Compounds Containing Pyrimidine and
Imidomethyl Uracil Radicals
the Na-salt of 2-phenyl-4-methyl-6-oxypyrimidine. Under the
selected conditions no compound with the imidouracil radical
could be obtained from Na-salt. They were produced by the
interaction of Ag-salt and the acid chloride of dialkyl phos-
phoric acid in dry toluene or xylol in a yield of from 51.6
to
~57-8 %. These compounds are low-melting crystalline solids.
They are easily soluble in organic solvents, less easily
soluble in water. It is a characteristic feature of all com-
pounds that in compounds with an ethyl radical solubility in
water is better than in compounds with normal and isobutyl
radicals. The authors tried to obtain n-butyl ester (Nr 7)
according to the method described (Ref 2). On this occasion,
however, a product was separated which according to its ana-
lysis corresponded to the acid imidomethyl uracil butyl
ester.
Individual synthesized esters were saponified. In the course
of saponification with hydrochloric acid (1-.1) usually
initial pyrimidines or imidomethyl uracil could be separated.
Card 2/3 Some of the synthesized compounds were examined by
M. A.

Esters of Phosphoric and Thiophosphoric Acids
SOV/62-58-11-9/26
Containing Heterocyclic Radicals.
Communication I. Ccmpounds Containing Pyrimidine and
Imidomethyl Uracil Radicals
Kudrina at the Kazanskiy filial Akademii nauk SSSR (Kazan,
Branch of the Academy of Sciences USSR) with respect to
their insecticide properties on Calandra granaria L. and to
toxic properties on mice. The results are shown (Table 2).
There are 2 tables and 4 references, 1 of which is Soviet.
ASSOCIATION: Khimicheskiy institut im. A. M. Butlerova
Kazanskogo
gosudarstvennogo universiteta im. V. 1. Ullyanova-Lenina
(Chemical Institute imeni A. M. Butlerov , Kazan' State
University imeni V. I. Ullyanov-Lenin)
SUBMITTED: March 21, 1957
Card 3/3

50)
AUTHORS: Arbuzov, B.A., Ukhvatova, E.N. SOV/62-58-11-22/26
TITLE.
On the Reaction of Trialkyl Phosphites With Nitrosyl Chloride
and Nitroxyl Chloride (0 reaktsii trialkilfosfitov s khloristym
nitrozilom i khloristym. nitrilom)
PERIODICAL: Izvestiya Akademii natxk SSSR. Otdeleniye
khimicheskikh nauk,1958,
Nr "t PP 1395 - 1396 (USSR)
ABSTRACT: In this brief paper the authors report on the
ascertainment that
in an interaction between trialkyl phosphites and nitrosyl
chloride
and nitroxyl chloride mainly an oxidation of trialkyl phosphites
into corresponding phosphates takes place. In the case of the re-
action of triethyl phosphite with nitroxyl chloride apart from
triethyl phosphate also a smaller quantity of a fraction was pre-
cipitated which corresponds to the tetraethyl pyrophosphate both
according to the constants and the analysis. In the case of
nitro-
syl chloride a similar.fraction was precipitated, which contained
smaller quantities of phosphorus, though. In the case of higher
homologs of phosphites the authors did not succeed in
precipitating
pyrophosphates, since the distillation of high-boiling reaction
products leads to their decomposition. There are 4 references,1
of
which is Soviet.
az~

BOY/20-121-1-28/55
AUTHORS: Arbuzov, B. A., Member, Academy of Sciences, USSR,
Isayeval Z. G.
TITLE; On the Reduction of the,63-Carene Oxide (0 vosstanovlenii
okisi,63_karena)
PERIODICALt Doklady Akademii nauk SSSR, 195B, Vol. 121, Nr 1, pp.
105-106
(USSR)
ABSTRACT: It is known that the oxide mentioned in the title may be
reduced
to an alcohol (C 10H18 0). When the authors investigated the
hydration of this oxide they found that two further products
with the same formula are produced from ik'. The first alcohol
is apparently identical with the 1-caranol of Kuozyuski and
Chabudzinski (Kuchinslziy and Khabudzinskiy) (Ref 2). An !,.lcohol
which was obtained by the authors from reduction of the 1-car-
anone-3 (purified twice -with p-nitrobenzoate and the acid
phthalic ether) has constants which are very close to the al-
cohol produced by the authors (purified by 3,5-dinitrobenzoate).
The two alcohols differ only by the melting point of the acid
Card 1/3 phthalic ether. In consequence of the oxidation of the

Gh the Reduction of the &3-Carene Oxide SOV/20-121-1-28/55
,A3-oxide-hydration product by chrome anhydride in acetic acid
a ketone C 10H16 0 was obtained which yields semioarbazide
(melting point 201 - 2020) in a quantitative yield. This ketone
is according to its constants and its melting temperature
identical with the I-caranone-3 (Ref 2) which is an isomeriza-
tion product of the,43-carene-oxide by sodium in benzene. The
aame ketone was obtained by the authors (in a low yield) from
the dehydration reaction of the P-carene-glycol by p-toluene-
sulfochloride in pyridine. In orderto be able to give a final
identification of the initially mentioned prodict, the authors
produced it by the action of sodium upon the A -carene-oxide in
benzene. From the alcohol reactions 3t5--linitrobenzoate of the
1-caranol-3 (from alcohol) and an acid phthalic ether were ob-
tained.'Since these two compounds did not show a temperature
depression of mixed samples with corresponding derivatives of
the&3-carene-oxide hydration product one of the products of the
catalytic hydration of the last mentioned oxide is bound to be
1-caranol-3. A further alcohol existed in the reaction products;
it turned out ot be oaranol-4, could, however, not be isolated.
Card 2/3 It might be one of the 4 possible stereoisomers of
caranol-3.

Q~~
On the Reduction of the A,-Carene Oxide SOY/20-121-1-28/55
The reduction of the A3-carene-oxide with LiLlH4yielded
caranol-4 (Ref 2). There are 8 referunces, 1 of which is
Soviet.
SUBUTTED: April 17, 1958
I. Terpenes--Chemical properties 2. Organic oxides--Reduction
3, Alcohols--Synthesis
Card 3/3

AUTHORS: ArbuaRy4-2"., Member, Academy of BOV/2o-121-4-19/54
Sciences, USSR, Vinogradova, V. S., Polezhayeva, N. A.
TITLE: On the Structure of the Products of the Interaction
Between
Some a-Haloid Ketones of the Carbocyclio Series and Tri-
ethyl Phosphite and Sodium Diethyl Phosphite (0 stroyenii
produf;tov Tzaimodoystviya nekotorykh a-galoidoketonov karbo-
taiklichookogo ryada a trietilfosfitom i dietilfoaforistym
natriyem)
PERIODICAL: Doklady Akademii nauk S53R, 1958, Vol- 121, Nr 4,
pp. 641 - 643 (USSR)
ABSTRACT: In the course of the past years the authors found that
the reaction of regrouping according to Arbuzov of tri-
ethyl phosphite with a halide ketones proceeds in a very
complicated way in the production of P-ketophosphinic aoid
others. Apart I'from the mentioned ethers mixed phosphoric
ethers are formed (Ref 2). Thus the investigation of the
first mentioned ethers was rendered more difficult and some
deviations of their chemical and physical properties were
Card I explainedt,(Ref 3)- It proved true that the reaction
according

On the Structure of the Products of tho Interaction
SOV/2o-121-4-19/54
Between Some a-Haloid Ketones of the Carbocyolic Series and
Triethyl
Phosphite and Sodium Diethyl Phosphite
to Mikhaelia-Bekker In the case of the interaction between
sodium diethyl phosphite and a-haloid ketones proceeds also
in a complicated way and that it also leads to the formation
of epoxy phosphinio acid others apart from the expected
ithers (Ref 4)- In this paper the structure mentioned in the
title is shown. The ketones are: a-chloro-cyclohexanone,
a-ahloro-a-methyl cyolohexanone, a-chloro-eyelopentanone
and ethers of bromine pyruvio acid. The investigation of the
product of interaction between a-ohloro-cyclohexanone and
sodium diethyl phosphite revealed (in contrast to Ref 6)
that it is neither an unsaturated ether of phosphoric acid
nor a phosphonium cyclohexanone ether. Its spectrum of
combination light dispersion does not contain the frequency
of the carbonyl group. These and other data show that this
product has the structure of a diethyl ether of epoxy cyclo-
hexane phosphinio &aid. This assumption was proved by the
synthesis carried out by the authors (Ref 4). Thus it was
proved that the last mentioned ether was concerned and no
Card 2 a-phosphonium. cyclohexanone. Somehow surprising was the

On the Structure of the P 'roducts of the Interaction
SOV/20-121-4-19/54
Between Some a-Haloid Ketones of the Carbocyclic Series and
Triethyl
Phosphite and Sodium Diethyl Phosphite
similarity between'the constants and the spectra of the
combination light dispersion of the products of the two
phosphites mentioned in the title acting upon a-chloro-
a-methylcyclohexanone. The mentioned findings show the
complicated process taken by this reaction. It leads to
the formation of unsaturated phosphoric acid ethers, ethers
of epoxy phosphinic acidsj in some casesq however, even
of.p-keto,phosphinic ethers (Ref 4); this depends on the
nature of the haloidl, the conditions of reaction and the
substituting alkyl radicalsj There are 5 references, 5 of
which are Soviet.
ASSOCIATION: Nauchno-issledovateltskiy khimicheskiy institut
im.A.M.
Butlerova pri Kazanskom gosudarstvennom universitete im.
V.I.Ullyanova-Lenina (Scientific Chemical Research Institute
imeni A.M.Butlerov, State University
imeni-V.I.Ullyanov-Lenin,
Card 3/ Kazan')

SOV/2o-122-1-19/44
A*JTJfORS: Arbuzov, B.A., Member, AS USSR, jeayeva, Z.G.
TITLE; Reaction Products of a-Pinene Oxide and 4~L 3Carene
oxide
With3Acetic Anhydride (0 produktakh reaktsii oki3ey a-pinena
i Z~L _karena s u~Jusnym an&idridom)
PERIODICAL: Doklady Adademii nauk SSSR, 1958, Vol.122, Nr 1,
PP- 73-7~
(USSR)
ABSTRACT: The authors continued their research on this subject
as well
as on the same reaction of the camphene oxide. It could be
proved that the reaction of these bicyclic terpene oxides pro-
ceeds on a complicated way. Mixtures of products are formed~
and an isous3ization of the oxides takes place. The present
paper
is intended to clear the structure of the acetates which have
been produced from the above oxides. As previously reported
(Ref 3), the yield of the acetate C J2H1802 with a-pinene oxide
does not surpass 30 whereas in t e case ofL'~13carene oxide
it remains below 22 The authors have performed the first
reaction in the presence of NaHCO 3, in order to conduct the
formation of the acetates C 1 H18 02mainly in the direction of
the suggested scheme. The laiter salt' bindsthe acetate ions
Card l/ and r6ducesthe formation of acetate-diols to a minimum.

Rea -Pinene Oxide and SOV/2o-122-1-19/44
Products of a
Carene Oxide With Acetic Anhydride
By this, it was proved that the a-pinene oxide couid.~b4
recovered unchanged to 40 %; the isomerization of th6' oxide
to a "campholene" aldehyde occurrddto a much lower extent.
Instead of the expected acetate, however, an alcohol C JjHj60
(yield 28 %) was isolated which is identical with the _rans-
carveol (Ref 4). By oxidation of this alcohol by means of
chromium anhydride in acetic acid, carvone was obtained. Accord-
ing to the statements of reference 3 the boiling point of the
acetate from a-pinene oxide is found in a broad temperature
range. By repeated fractionation, apart from "campholene"
aldehyde and sobrerol acetate 3 further substances with the
same empirical formula C12H1.0 with a total yield of 31 %
were isolated: 1) A product WiL lower boiling point (79 -
800/3mm) and with a double-bond in the molecule. By its saponi-
fication with 7 % NaOH solution in alcohol-water an alcohol
with a ring consisting of 4 links was produced, which rather
might be identical with a pinocarveol(II) or still more with
the-trans-pinocarveol (Ref 7). 2) A somewhat higher boiling
(87 87,50/3mm) product C H 0 with two double-bonds. By
saponification with lo %liad Solution in alcohol-water an
Card 2/4 alcohol similar to the trans-carveol resulted.

Reaction Products of a-Pinene Oxide and 30V/20-122-1-19/44
,(N,3 Carene Oxide With Acetic Anhydride
3) The boiling point of the third product C 12H1802 was still
higher (89-89,50/3 mm). The investigation of the latter is
continued.. The reaction of the & 3 carene with acetic anhydride'
does not proceed smoothly. The products of reaction consist of2
1) The hydrocarbon fractions (3,5A) and 2) the products con-
taining carbonyl (VO). They will further be -investigated. There
are 11 references, 4 of which are Soviet,
ASSOCIATION: Khimi.cheskiy institut im. A, M. Butlerova pri
Kazanskom,
gosudarstvennom universitete im. V. 1. Ullyanova-Lenina
(Chembbry Institute imeni A. M, Butlerov of the Kazan'
State university imeni V. I. Ullyanov-Lenin)
SUBMITTED; May 7, 1956
Card 31~

50) MM I BOOIC MMMTMION SOV/2148
Arbuzov., Boris Aleksandrovich., AcadaOcian
Poefororgonicheskiye soyedineniya,
(Orgenic.Phoopboras.comj?ounds), m6scov., 1zd-vo
"Zzaw"O" 1939*. (Series: Vses67UznQYe O"OshchestvO po raspros-
tranenl~m politicheWdkb A zamabm7kh ==iy,, Serlya 1Xj, 1959P v7P-
37,,000 copies printed,
Sponsoring Agency: Vaeso yuznoye obshchestvo po rasprostrananiyu
politicheakfIcb
I nomebykh amly.
Ed.: I. B. Faynbo3mj Tech. Ed.1 ye. V. savchenko.
PURPOSEi The booklet Is Intended for the Vnerel reader#'
COVEME: The booklet discusses the progress of chemical
investigations of
organic cOmpOundse The anthor gives essential information on the
use of
these compounds in agricult=e (insecticides), in medicine (for
treatment
of glancomat paralysis),, and in the manufacture of plastic
materials
Card 1/2

M
50) SOV/62-59-1-7/38
AUTHORS: Arbuzov, B. A., Vinogradova, V. S., Polezhayeva, N. A.
TITLE: Esters of O-Ketophosphinic Acids (EfirY ~-ketofosfinovykh
kislot) Communication III. On the Structure of Products
Resulting From Interaction Between Certain Halogen Ketones
With Triethyl Phosphite and Sodium Diethyl Phosphite (Soob-
shcheniye 3. 0 stroyenii produktov vzaimodeystviya nekotorykh
galoidoketonov a trietilfoafitom i dietilfosforistym natriyem)
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheskikh nauk,
1959j Nr 1, pp 41 - 49 (USSR)
ABSTRACT: In the preceding papers (Refs 1-3) the authors found
that
the esters of P-ketophosphinic acid synthesized in various
ways differ considerably as to their physical constants
as well as to their behavior towards dinitro-phenyl hydra-
zine. The differences are particularly evident in ultra-
violet spectra. The causes for these differences, however,
have not yet been made clear. In order to obtain preparations
as pure as possible the authors of this paper distilled pre-
parations earlier obtained as well as new ones in rectifica-
Card 1/3 tion columns with an efficiency of 17 theoretical
plates.

Esters of P-KetophoBphinic Acids. Communication III.
SOV/62-59-1-7/38
On the Structure of Products Resulting From Interaction
Between Certain
Halogen Ketones With Triethyl Phosphite and Sodium Diethyl
Phosphit,
The constants of the pure preparations are given in table
Ultraviolet absorption spectra were recorded by means of
the spectrometer SF-4 in methyl alcohol solution. Raman
spectra were recorded by means of the three-prism spectro-
graph ISP-51. The investigations carried out have shown
the following data: on the effect of triethyl phosphite
on chloro and bromo acetone (beside isopropyl ester of the
diethyl phosphoric acid) as well as on bromoethyl ketone
eaters of corresponding P-ketophosphinic acids are formed.
Products of potassium derivatives of phosphonium acetone
and methyl-phosphonium acetone, which were synthesized by
methylation with methyl iodide, possess the structure of
esters of the P-Icetophosphinic acid. On the effect of
sodium diethyl phosphite on chloro and bromo acetone as
well as on bromo-a-bromo-ethyl ketone esters of the epoxy
phosphinic acid are formed. Their strncture was confirmed
by a synthesis carried out in another way and by Raman
spectra. Contrary to Kreutzkamp's and K&yser's data, not
Card 2/3 the unsaturated isopropyl ester of phosphoric acid
is

Esters of p-Ketophosphinic Acids. Communic:',inil III. J 0 V / 6
2 - 5 9 - 1 - 7
On the Structure of Products Resulting Fr-~ : 1,,!.~!racttlinn
Between Cet-tain
Halogen,Ketonen With Triethyl Phosphite anfli 3o;!.~iun
Di-1-11-~yl Pho,-,j)1iitc
produced on the effect of. oiet!.yl phosphite on chloro
.and bromo acetone, but thc cstI7~r of' (--poxy-propyl
phoophinic acid as well as 1,"I.-,. .honiiii-! :~(iotono. Tlia
11rodlirt-
syntheoized by the interaction of mcthyl-y-chloro-propyl
ketone with sodium diallkyl plio!~phitc Vie "'tructurv.
of the ester of 1-methyl-to-'~.i,Liliydrofur.-i-,i
phonphinic-1-acid,
There are 1 figure, 2 zmil 13 referenceo, 6 of
which are Soviet.
ASSOCIATION:% Nauchno-isaledovatellskiy ir~itllmt in. A. "'k.
Butlerova
KazanskoLro gosudarstvenno.-o iiniversitct-i im. V~ i,
Ulljanov~,,-
Lenina (Scientific Reaearch It,.,Litutc i-ir~ni A. 114.
Bnt.1Q1-ov
of the Kazan' State Univpr,,-,~ "--,r imeni V. 1. Ullyanov-Lonin)
SUBMITTED: May 11, 1957
Card 3/3

Esters of #-Ketophosphinic Acids. Communication 4-
SOV162-59-2-13140
Infrared Spectra of Reaction-Products of*(-Halogen
Ketones With Triethyl Phosphite and Sodium Diethyl Phosphite
The spectra were obtained on the double beam infrared
speatrophotometer which had been constructed on the basis of
the monoahromator IKS-11 in the works FIAN (Ref 3). The
preparations were supplied by V. S. Vinogradova. The
investigation of the infrared spectra of reaction products of
bromo-acetone, methyl-vC-bromo-ethyl ketone and bromo-mothyl-
ethyl ketone with triethyl, phosphite confirmed their
structure
to be that of esters of the fl-ketophosphinic acids (absorp-
tion band 5.84-5-85,m of the carbonyl group). The spectra of
products of bromo-acetone and methyl-ok-bromo-ethyl ketone
with sodium diethyl phosphite have shown that they possess
the structure of esters of the epoxy phosphinic acids. This
is shown by the missing absorption band of the carbonyl group
and the presence of an absorptifn band 11.80, li.98,A being
characteristic of the epoxyl group. Conclusions as to the
presence of enolization could not be drawn for the esters
investigated on the basis of their infrared spectra. There
Card 2/3 are 8 figures and 6 referenaes, 4 of which are
Soviet.

Esters of*P-Ketophosphinic Acids. Communication 4-
SOV/62-59-2-13/40
Infrared Spectra of Reaction Products of04-Halogen
Ketones With Trietkwl Phosphite and Sodium Diethyl Phosphite
ASSOCIATIONt Fizicheskiy institut im. P. N. Lebedeva Akademii
nauk SSSR
(Physics Institute imeni P. N. Lebodev of the Academy of
Sciences, USSR) Hauchno-issiedovatellskiy institut im.
A. M..Butlerova Kazanskogo gosudarstvennogo universiteta im.
V. I. Ultyanova-Lenina (Scientific Research institute imeni
Ai.M& Butlerov of the Kazan' State University imeni V. I.
Ullyanov-Lenin)
.SUBIZITTED: May 11, 1957
Card 3/3

.50)
SOV/30-59-3-23 1 161
AUTHORS:
Arbuzov, B* A*) Academician,
Xiprianov, A. I., Academictan of

.the A!1Yr_S8R
TITLE,
Congress on
Ch~mics%l Engineering (Kongress po promyshleri.noy

khimii)
PERIODICAL:
Vestnik.Akademii nauk SSSR, 1959, Nr 3, pp 82-85
(USSR)
ABSTRACT:.
The XXXI International Congress took place in
LiAge, Belgium

from September 7 to 12~ 1958- It was attended by
more than

1000 chemists and engineers of various countries. The
Soviet

delegation was represented by B. A. Arbuzov, G. A.
Razuvayev,

K. A. Kocheahkovi A. 1. Kiprianov, S. 1. Zav'yalov,
and a

number of scientists and engineers of scientific branch
re-

search institutes and enterprises of the chemical industry.

The discussions covered the whole range of chemical
engineering,

from atomic -metallurgy to pharmaceutical products.
The Soviet

chemists deliirered'the following reports: V. A.
Kargin and

M. No Shteding reported on the inhibiting properties
of

stabiliieral K. A. Kocheshkov spoke of the effect of r'-

radiation on the synthesis of orgpo-metallic stabilizers and

catalysts for plastics; B* A. Arbuzov reported on the re-
Card
1/2
generation of carene and pinene oxides; A. 1. Kiprianov and

T
1r,11A.- . .......

5 (3)
.AUTHORS: Arbuzov, Be A., Zoroastrovaq Ve Me SOV/62-59-6-14/36
TITLE: The Esters of the Phosphoric- and Thiophosphoric Acidq Which
Contain Heterocyclic Radicals (Efiry fosfornoy i tiofosfornoy
kislot , soderzhashchiye geterotsiklicheskiye radikaly).
Communication 2. Alkylation of Some Heterocyclic Compounds by
Means of the Derivatives of the Phosphoric- and Phosphorous
Acid (Soobshcheniye 2a Alkilirovaniye nekotorykh geterotsik-
licheskikh eoyedineniy proizvodnymi fosfornoy i fosforistoy
kislot)
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh
naukt
1959, Nr 6, pp 1037 - 1040 (USSR)
ABSTRACT: In a previous paper (Ref 1) the authors described a
series of
eaters of phosphoric and thiophosphoric acid with pyrimi-
dine and imidomethyliiracil radicals. The compounds obtained
proved to be biologically highly active. The present paper is
a continuation of the first one. The authors wanted to obtain
esters of the phosphoric acids with heterocyclic radicals
(thiacine, benzoxazole~ and benzothiazole), and to investigate
their properties. Besides the substances expected by the in-
Card 1 fluence of dialkylphosphoric acid chloride upon the potassium

The Esters of the Phosphoric- and Thiophosphoric Acid,
Which Contain Heterocyclic Radicals. Communication 2.
Alkylation of Some Heterocyclic Compounds by Means of
the Phosphoric- and Phosphorous Acid
SOV/62-59-6-14/36
the Derivatives of
salts of 49696-trimethyl-6H-193-thiazine-2-thiol (I), 2-mer-
captobenzoxazole (II) and 2-morcaptobenzothiazole (III)v also
alkylation products were produced of thiol. In the
experiment-
al part the following reactions are described; 1) K-salts of
(I) with acid chloride of aiethyl phosphoric acidi2) K-salts
of (I) with acid chloride of the di-isobutyl phosphoric acidl
3) K-salta of (II) with acid chloride of the
Aiethylphoaphoric
aoidl 6) K-salts of (III) with acid chloride of the diethyl
phosphoric acid. Alkylation products of thiol were in good
yield obtained by reaction of trialkylphosphites on the di-
sulphides of the above mentioned heterocyclic compounds; 4)
Disulphide of benzoxazole with triethylphosphite; 5) 2-ben-
zoxazole sulphenylchloride with triethylphosphitei 7) disul-
phide of benzo thiazole with triethylphosphitel 8) disulphide
of benzo thiazole with the ethylester of the ethyleneglycol
phosphoric acid. There are 5 references, 3 of which are
Soviet.
Card 9,

5 (3)
AUTHORS: Isayeva, Z. G., Arbuzov, B. A. SOV/62-59-6-16/36
TITLE: On thi Reduction of the Oxides of a-Pinene and of the Oxi
es
of 6 -Carene (0 vosstanovienii okisi a-pinena i okisi
karena)
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheskikh naukp
1959, Nr 6, pp 1049 - 1057 (USSR)
ABSTRACT: The reduction of the oxides mentioned in the title by
lithium
and aluminum hydride was not possible, what is proved by pub-
lications (Refs 1-17)- In the present investigation the oxides
could be reduced by hydrogen in the presence of Renay -nickel
under sharp conditions. a-pinene was reduced at 135-175 0 and
a pressure of from 60-100 atmospheres,,63-carene at 175 _200 0
and a pressure of from 50-80 atmospheres. The red-detion of a-
pinene leads to the formation of 2 alcohols of the composition
CioH16 0. The hydration reaction was accompanied by an isomeri-
zation of the a-pinene under formation of a ketone of the same
composition, which-is similar to the thermal isomerization and
the oxidation productsof the alcohol C 10H18 0. The ketone ob-
Card 1/3 tained by the thermal isomerization of a-pinene oxide
may be

S#62-59-6-16/36
Oxides ofA&3-Carene
reduced by lithiumaluminum hydride to CjOH180 in 2 isomer al-
cohols which, however, are not identical with the alcohols ob-
tained by reduction of a-pinene oxide on Renay-nickel. Reduc-
tion of a-pinene oxide: H
OR(II)
Pinokampheol (II) and pinanol (I) are produced. The reduction
of pinokamphon produced from hyssop oil on lithiumaluminum hy-
dride also leads to an alcohol of the composition C10"180, which
differs from the aforementioned one. The A3-carene oxide is re-
duced on Renay-nickel to an alcohol of the composition C1 01801
which isomerizes into a ketone ClOH160 when being heated. The
different reductions are described in detail in the experiment-
Card 2/3 al part. A table gives the results of the thermal
isomerization
On the Reduction of the Oxides of a-Pinene and of the

On the Reduction of the Oxides of a-Pinene and of the
SOV162-59-6-16136
Oxides of A3-Carene
of a-pinene. There are I table and 12 references, I of which
is
Soviet.
LSSOCILTION: Nauchno-iouledovatellskiy institut im. A. M.
Butlerova Kazan-
11kogo gosudaretvennogo universiteta im. V. 1.
Ullyanova-Lenina
(Scientific Research Institute imeni A. M. Butlerov of the
Kazan' State University imeni V. 1. Ullyanov-Lenin)
SUBMITTM)-. August 15, 1957
Card 3/3

50) SOV/62-59-9-10/40
AUTHORS: Arbuzov, B. A., Zoroastrova, V. M., Saykina, M. K.
TITLE: Thermographic Studies of the Isomerization Reaction-of the
Glycol Phosphorous Acid Eaters, Containing a Six-membered Ring,
Under the Action of Alkyl Halides
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh
nauk,
1959, Nr 9, pp 1579-1584 (USSR)
ABSTRACT: The authors had carried out previous investigations
similar to
those mentioned in the title, in which they proved that the
isomerization reaction proceeds in two phases. They also suc-
ceeded in finding information on the influence of the radical
structure exerted on the capacity of the esters to isomerize
(Arbuzov and Razumova, Ref 2). In the present paper the in-
vestigations are continued with the reaction of the esters of
trimethylene glycol- (I) and a-methyl trimethylene phosphorous
acid (II) with alkyl halides. The methods of investigation were
similar to those of reference 1. A pyrometer of the PK-52-type
was used and butylphthalate was taken as standard. Table 1
contains the physical constants of the compounds investigated.
Card 1/3 Only one phase could be observed on the thermograms of the
metlWl-

SOV/62-59-9-10/40
Thermographic Studies of the Isomerization Reaction of the
Glycol Phosphorous
Acid Eaters, Containing a Six-membered Ring, Under the Action
of Alkyl Halides
ethyl- and n-propyl esters of compounds (II) and the methyl-
and benzyl esters.of (1). The experimental data are shown on
table 2 and figures 1-7- Herefrom the following could be con-
eluded: the isomerization process of alkyl glycol esters with
six-membered rings occurs under participation of the alkyl
radical without destruction of the ring according to the
scheme already earlier assumed by Arbuzov; a simultaneous
forma-
tion of the esters of alkyl phosphinic acid takes place. The
isomerization of the phenyl eater of (I) occurred unexpectedly
also in one phase only, a ring opening was, however, observed
in the analysis of the reaction products. A mixture of phenyl-
y-iodine propyl ester of methyl phosphinic acid forms when
metbyl iodide aote upon the phenyl eater of 1. In the
isomeriza-
tion reaction of the ethyl eater of pyrocatechol phosphorous
acid with ethylbromide again or-ly an exothermic effect was ob-
served. A cyclic pyroaatechol ester of ethylphosphinic acid was
formed, which is in accordance with the results of Arbuzov and
Valitova (Ref 9). The ester radicals were therefore found to
Card 213 exert an influence on isomerization. There are 7
figures,

sovl62-59-9-10140
Thermographic Studies of the Isomerization Reaction of the
Glycol Phosphorous
Acid Esters, Containing a Six-membered Ring, Under the Action
of Alkyl Halides
3 tables, and 9 references, 7 of which are Soviet.
ASSOCIATION: Nauchno-insledovatellskiy institut khimii im. A.
M. Butlerova
Kazanskogo Gosudarstvennogo uniyersiteta im. V. I. Ullyanova-
Lenina (Scientific Research Institute of Chemistry imeni
A. M. Butlerov of the Kazan' State University imeni V. 1.
Ullyanov-Lenin)
SUBMITTED: January 9, 1958
Card 3/3

5.3400
AUTHORS:
TITLEt
PERIODICAL:
77067
sov/62-59-12-li./43
Arbuzov, B. A., Ehismatullina, A. 0.
Diels-Alder Synthesis With Levopimaric Acid
Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh
nauk, 1959, Nr 12, pp 2126-2129 (USSR)
ABSTRAM Crude resin acids of the galipot, Pinus inaritima, con-
taining 40% levopirnaric acid, were condensed with
acrolein, acrylonitrile, vinyl acetate, and methyl
acrylate, in dry ether under carbon dioxide at
40-600, in sealed tubes. The obtained products were
purified as cyclohexylamine or diacetoneamine salts:
00"
C 1, 0011 OOH 001i
Ht
+ 1II-R Oft
H, ti,
R = DID, CN, DCOCH, C0001'.
Card 1/3

Diels-Alder Synthesis With Levopimaric 77067
Acid sov/62-59-12-ii/43
Card 2/3
It was not determined whether the products had
structure (II) or (III). The acrolein adduct, re-
generated from the amine salt with boric acid,
had mp 50-620J ICLID = +37-50 (all rotation measurements
were made In ethanol); it formed a semicarbazone
0
MP 216-2180, [Ct]D = -8.7 . The0acrylonitrile adduct,
similarly obtained, had mp 80-90 1 [CL]D = -12-50.
The vinyl acetate adduct, after regeneration, had
mp 67-830, [CLID = -260, neutralization equivalent,
103 (calculated, 103). The methyl acrylate adduct,
after repeated recrystallization from aqueous ethanol,
had mp 134-1380. The results of elemental analysis, in
all cases., were in good agreement with calculated
percentages. There are 2 figures; and 7 references,
3 Soviet, 2 Swiss, 1 German, 1 U.S. The U.S. ref-
erence is: 0. C. Harris, J. Am. Chem. Soc., 11, 3671
(1948).

Diels-Alder Synthesis With Levopimaric 77067
Acid sov/62-59-12-11/43
ASSOCIATION: V. I. Ullyanov-Lenin Kazan State University
(Kazanskiy
gosudarstvennyy universitet imeni V. I. Ullyanova-
Lenina)
SUBMITTED: April 24, 1958
Card 3/3

5.3400
77068

sov/62-59-12-12/43
AUTHORS:
B. A Konovalov, A. I.
TITLE:
The
Diels-Alder Synthesis. Communication 1. The Spectro-

photometric
Study of the Diels-Alder Synthesis
PERIODICAL:
Izvestiya Akademii
nauk, SSSR. Otdeleniye khimicheskikh

rauk, 1959, Nr 12, pp 2130-2134
(USSR)
.4STRACT.
The purpose of this work was to test the assumption
that

D. A. reagents (dienes and dienophiles) may reversibly

form
molecular compounds, which may then react irrevers-

ibly. The
absorption spectra of the molecular compounds

are determined by an
intermolecular charge transfer and

should be found in the visible or
the ultraviolet region

of the spectrum. The absorption of chloroform
solutions

was measured on a SF-4 spectrophotometuer. Concentrations

optimum optical density values (1 cm cell)
giving the

were used in the order of 0.001 M in maleic anhydride).
(

The following conclusions were made on the basis of
Card 1/2
spectral
investigations: Formation of molecular compounds

I-lay -- ~L-t i el'e

AUTHORS:
Arbuzov, 13. A.v Ukhvatova, E. W. SOV/79-29-2-30/71
TITLE:
Synthesis...of..the.Esters.of Some.Phosphinic Acids and
Phosphoric

Acid (Sintez efirov nekotorykh fosfinovykh i
fosfornoy kislot)
PERIODICAL:
Zhurnal obBhchey khimiij 1959, Vol
29, Nr 2, PP 503-507 (USSR)
ABSTRACT:
According to an American
patent (Ref 1) dioxolanes are readily

cleft by the action of
acyl chlorides into the acyl derivatives

of oxyhalogen others

CH2-0,,~
-
-0
CH Cl
l
C
H C
O

-
--
-C
.
CH + CH Coc
CH
O
H2
1 2 3 3 2 2
--O--'
CH

2

It was not confirmed that also other halogen anhydrides
break

the dioxolane ring (as shown e.g. in scheme 2). The
uncomplicat-.

ed synthesis of P-acetoxyethyl chloro-methyl ether
induced the

authors to use this ether also for the synthesis of
phosphi-

nates. It results from the experiment that the complete
esters

of phosphorus acid readily react with P-acetoxyethyl
chloro-

methyl ether (Scheme 3). The constants of the esters
obtained

are listed in the table. Many thiophosphoric'esters
proved to
Card 1
be insecticides, yet the authors did not succeed
in obtaining

Synthesis of the Eaters of Some Phosphinic Acids and
SOV/79-29-2-30/71
Phosphoric Acid
esters of thiophosphoric acid with a P-acetoxy ethoxy-methyl
radical in pure state. The esters of phosphoric and thio-
phosphoric.acid with heterocyclic radicals as insecticides are
of great interest (Ref 2). Therefore, the authors i synthe.sized
phosphates with thiazole and thiodiazole radicals. On the action
of chloric anhydride of diethyl phosphoric acid o* the sodium
salt of 4-methyl-2-oxy thiazole the authors obtained a mixed
ester of phosphoric acid in good yield (Scheme 4). By the re-
action of the chloric anhydride of di6thyl phosphoric acid
with 4-methyl-2-amino thiazole the corresponding substituted
amide was obtained (Scheme 5). The accessibility of 2,5-di-
mercapto thio-3,4-diazole (Ref 4) induced the authors to cause
it to react with the chloric anhydride of diethyl phosphoric
acid according to scheme 6. According to the results of analy-
sis this formation is probable. There are 1 table and 5 refer-
ences, 3 of which are Soviet.
"e,
lk~
Card 2/

50)
SOV/79-29 -8 -36/81
AUTHORS:
Arbuzov, B. A., Bogonoatseva, N.
P.
TITLEi
Syntheses on Me Basis of Ethyl-oxy-methyl-phosphinic
Acid
PERIOD1CAL:
Zhurnal obshchey khimii, 1959, Vol 29, Nr 8, pp
2617-2622 (USSR)
ABSTRACT:
The authors investigated the
reactiorsof the compound

(C2H50)2POCH2 ONa(I) most useful for
this purpose, with the acid

chloride of the diethyl-phosphoric
acid, the ethyl ester of the

chloroacetic and chlorocarboxylic
acid, the chlorohydrin of ethy-

lene glycol, silicon
tetrachloride, phosphorus trichloride,phos-

gene and thionyl
chloride. The first four reactions proceeded

normally. With the
acid chloride of the diethyl phosphoric acid,

the diethyl
phosphate of the ethyl-oxy-methyl-phosphinate was

obtained
according to scheme 1. With ethyl-chloroacetate, the

reaction
yielded the a-diethyl-phosphono-al-carbetlioxy-dimethyl

ester
(Scheme 2). With ethyl -ohlorocarbonat e, the composition

approaches the ethyl-etlioxy-methyl phosphinate (C 2H 50)2 POCH2
OC2H5

(Ref 2) under evolution of carbon dioxide, and diethyl
carbonate

separates out (Scheme 3). With the chlorohydrin of
ethylene

glycol, the ethyl-oxy-methyl phosphinate was obtained
(confirmed
Card 1/2
by the analysis). The reaction with SICI
and PC1
gave no de-

4
3

Syntheses on the Basis of Ethyl-oxy-methyl-phosphinic Acid
SOV/79-29-8-306/81
finite products, with the exception of ethyl-oxy-methyl phosphi-
nate. The reaction with phosgene yielded a liquid product which
neither corresponds with compound (II) nor (III), but is more
closely allied to (II) (Scheme 4). In the reaction with thionyl
chloride, the following compounds were separated: diethyl sulfite,
triethyl phosphate, ethyl-oxy-methyl phosphinate, and two more
products which correspond with the formulas C 6H2o07P2 and
C6H1406P2- To the first liquid product, stracture (IV) could
possibly be assigned; the second crystalline product corresponds
with structure (V). The structure of compound (V) was confirmed
by its synthesis by means of ring closure from two molecules
of ethyl-oxy-methyl phosphinate, or of its acetate on heating
with sodium alcoholate. There are 5 references, 2 of which are
Soviet.
ASSOCIATION: Nauchno-issledovatellskiy khimicheskiy institut pri
Kazanskom
gosadarstvennom universitet (Scientific Chemical Research Insti-
tute, Kazan' State University)
SUBMITTED: June 9, 1956
Card 2/2

50) SOV/79-29-8-61/81
AUTHORS. Viltehinskaya, A. R., Arbuzoyj_l.__A. ,
TIAE: Diene Synthesis of Alloooimene With Asymmetric Dienophils
PERIODICAL: Zhurnal obshchey khimii, 19599 Vol 29, Nr 8g pp
2718-2723 (USSR)
ABSTRACT: It was proved by the authors (Ref 1~ and at the same time
by
other research workers (Refs 2, 3) ihat the diene synthesis of
alloocimene with the anhydride of maleio acid takes place at the
carbon.atoms 41,7 (Scheme 1). In the case of asymmetric dienophils
the affiliation to the atoms 4,7 can yield two isomers (II) and
(III) for alloooimene (-Scheme 2). No definite data are to be
found in publications as to whether this synthesis yields (II) or
(III) or a mixture of both (Refs 29 4). In order to determine the
structure of the products of the diene synthesis of alloocimene
with asymmetric dienophils with regard to the question whether the
results are (II) or (III), the synthesis of alloocimene with
acrolein, methyl acrylate, and the nitrile of acrylic acid was
carried out and their structures were determined. The structure
of the product of alloocimene and aorQlein obtained earlier by
B. A. Atbuzov (Ref 5) was determined by dehydrogenation over the
Card 1/3 palladium catalyst. The result was a crystalline compound
which

.),-ene Synthesis of Alloocimene With Asymmetric
SOV/79-29-8-61/81
i. )ienophils
according to its melting point and that of its picrate as well
as its ultraviolet speotrump proved to be the 2,3,6-trimothyl-
naphthalene (Pig). This formation proves that the structure
of the adduction of alloooimene with aoroiein is (II,X-CRO)
(Scheme 3). The reaction of alloocimene with the methylaorylate
yielded an adduct with an 81,5% yield. The structure of the
esters as compound (II) (X-COOCH 3) was proved according to
scheme 4- In the dehydrogenation of the adduct over the
palladium catalyst the eater IV) was obtained, and when (IV)
was saponified the free acid R) resulted. Its oxidation
yielded the pyromellitic acid which was identified in the form
of its esters (VI)(Ref 10). Compound (VII) resulted from the
dehydrogenation of the adduct of alloocimene with
methylacrylate
by means of sulphur and sodium sulphite. The nitrile of acrylic
acid smoothly reacts with alloocimene. The structure of the
resulting adduct as adifipound (II) (X=CN) was proved
according to
scheme 5. Thus the affiliation of the dienophil takes place in
the case of the above diene syntheses with a formation of the
Card 2/3

Diene Synthesis of Alloocimene With Asymmetric
SOV/79-29-8-61/81
Dienophils
adduct (II). The formation of adduct (III) in other cases
is,
however, not impossible. There are I figure and 13
references,
6 of which are Soviet.
ASSOCIATIONt Nauch*ao-iseledovatellskiy khimicheskiy
institut pri Kazanskom
gosudarstvennom universiteteaidKazanakiy gosuda-rstvennyy
meditsinskily institut (scientific Research institute of
Chemistry at the Kazan' State University and Kazant State
Medical Institute)
SUBMITTED: June 16# 195a
Card 3/3

5'. ~2, 3)
I

.oWTHORS.-
V/20-127-6-20/51
so

lvin66 rova, G. Mot Perfillyeval I. A.
TITLE:
Addition of
Phonylphosphin6 to Unsaturated Compounds
PERIODICAL:
Doklady
Akademii nauk SSSR, 1959P Vol*127, Nr 6, pp 1217-1220

(USSR)
ABSTRACT:
After a survey of publications (Refs.1-4). the authors
indicate

brief results of their-inveAig~ationb made in recent
years on the

addition mentioned in the title: they intenaed to
obtain

bifunctional, phosphorus-containing compands, It has
become

evident that phanylphosphinev in the presence of a
catalyst and

on heatingg oan be easily added to the acrylics and
methaorylic-

acid esters. Be'sides the addition productst small
quantities of

oxides of the cor'responding-phOBphines-are
produced by Dxidation

of the tertiary phosphines forming. The
addition of pheiylphospbine

to allyl alcohol proceeds under the
influence of cataly6ts which

produce free radicals (of the
dinitryl-azo-bis-isobutyrio.aoidp

see Equation). Table I shows
the compounds obtained and their

constants. For obtaining various
derivatives, the authors

repeated the experiments by Mann (Ref
3). Here, A-oyano-ethyl-
Card 1/2
phenylphosphinep
di-(P-cya~io-athyl)-phenylphoErphiney~ and the oxide

Adtfition of Phenylphosphine to.Uneaturated Compounds
SOT/20-127-6-20/51
of the latter, were Isolated. By a reduction of the di-(A-cyano-
ethyl)-pbenylpliosphine by means of lithium aluminum hVdriae,
di-(A-amino-propyl)-phenylphosphine was produed.. The tertiary!
phosphines obtained are-easily oxidized by the atmospheric oxygen
(as derivatives of trivalent phosphorus) into the corresponding
phosphine oxidoe, and can also add sulpbur. Table 2 shows
constants of the 3 last-mentioned compounds obtained. rinally,
the authors carried out the interaction reactions of ~henyl-
phosphine with acroleing methacrylic acid, ejhylene okide, and
allyl bromide. There are 2 tables and 5 references*
ASSOCIATION: Institut organicheskoy khim:Li Kazanskogo filiala
Akademii nauk
SSSR (Institute of organic Chemistry of the Kazan' Br.Anch of the
Academy of Sciences, USSR)
SUBMITTEDt JUne 59 1959
Card 2/2

5~3)
A THORS: Arbuzov, B. A.f Academician, SOV/20-128-1-21/58
~ia~ao~a,~.' S.t Polezhayeva, N. A.
V Ino
TITLE:- Diethyl Ester of Cyclohexanone-2-Phosphini- Acid
PERIODICAL: Doklady Akad.emii nauk SSSR, 1959, Vol 128, Nr 1, PP
81-84
(USSR)
ABSTRACT: Tn the present paper the authors synthesized the diethyl
ester of cyclohexanone-2-phosphinic acid on the basis of
a,dl-dibromo oyclohexanone. By reaction of triethyl phosphite
upon a,al-dibromo cyclohexanone the diethyl phosphinic ester
of the enol form of oyclohexanone-2-phosphinic ester (III) was
obtained with the following constants: boiling point
172.5 - 1730/2.5 mm; d20 1-1885; n20 1.4652. This compound
0 0
was converted into the diethyl ester of cyclohexamone-2-phos-
phJjnic acid by means of ethyl alcohol. The molecular refract-
ion of oyolohexanone phosphinic ester1s placed between the
values which were computed for the ketone- (IV) (57.06) and
for the enol form M (58-1l)- Figure I shows its ultraviolet
absorption spectra in aqueous solution (curve 1) in methyl
Card 1/2 alcohol solirLion (curve 2) and in isooctane (curve 3).
Figure 2

Di;bthyl Eater of Cyclohexanone-2-Phosphinic Acid
SOV/20-128-1-21/58
gives the ultraviolet absorption spectrum in methyl alcohol
solution with content of sodium methylate. With the example
of the dietbyl eater of cyclohexanone-2-phosphinic acid it
was demonstrated that a ketoenol tautomerism may occur in
phosphinic esters containing a group of ketones in P-position
within the hydrocarbon radical present in phosphorus. There
are 2 figures and 8 references, 3 of which are Soviet.
ASSOCIATION: Nauchno-isaledovateliskiy institut im. A. M.
Butlerova.
Kazanskogo gosudarstvennogo universiteta im. V. I. Ullyanova-
Lenina (Scientific Research Institute imeni A. M. Butlerov
of the Kazan State University imeni V. I. Ullyanov-lenin)
SUBMITTED: June 5, 1959
Card 2/2

ROBINZON, Telizaveta Abelevw. Prinimal uchastiya
BOGORODSKAU , K.I..
nauchnyy sotrudnik. AgM_V.,_D*A
.-., nkademik, otv.red.;
NUESSEROV. K*G., red,izd-va; DORWINA, I.H.,
takhn.red.
[Petroleum in the Tatar A.S.S.R.] Nefti Tatarskoi
ASSR. Izd.2.,
perer. i dop. Moskva. Izd-vo Akad.nauk SSSR, 1960.
273 p.
(MIRA 13:8)
1. Sektor geologii neftyanykh mestorozhdaniy
Kazakhstanskogo
filisla Akademii nauk SM (for BogorodBkoya).
(Tatar A.S.S.R.-Petroleum)

5.54o6
78o66

sov/62-6o-1-12/357
AUTHORS:
Arbuzov, B. A., Ko-novalov,
A. 1.

TITLE:
Diels-Alder Synthesis. Communication 2. The Spectro-

photometric Study of the Diels-Alder Synthesis of

p-Benzoquinone
and CL-Naphthoquinone
PERIODICAL:
Izvestiya Akademit nauk.
Otdelenlye khtmicheslcikh

nauk, 1960, Nr 1, pp 68-72 (USSR)
ABSTRACT:
Spectrophotometric studies indicate that in the reactions

of p-benzpquinone with cyclopentadiene, Isoprene, and

piperilene,
the formation of monoadducts as well as

bis-adducts is pre-ceded by
formation of intermediates.

In the case of isoprene and piperilene,
the reaction,

at room tempprature, stops at the stage of the mono-

molecular complex of the mono-adduct with the diene.

The reaction
of CL ap~hthoquinone Involves an intermediate.

In solutions of
CL-laphthoquinone In isoprene and piper-

ilene there is no
absorption Indicating the presence

of any intermediate complex.
This can be explained
Card 1/2
by the assumption that the rate of
conversion of the
C

AUTHOR: ArbuzovL-B. -AiAcademician S/030J60/000/03/033/044
q BO15/B0O7
TITLE: The Chemistry of Organophosphorue Compounds and Their Use
PERIODICAL: Vestnik Akademii nauk SSSR, 1960p Nr 3s PP 103 - 105
(USSR)
TEXT: The Second Conference on the Chemistry and Use of
Organophosphorus Com-
poundewas held in Kazan' from November 26 to December 1, 1959- It
was attended
by more than 400 chemists, physiologiatep physicians,
entomologists, and
agronomists. Altogetherg 122 lectures were delivered. B. A.
lrbuzov spoke about
the development of the chemistry of organophosphorus oompounds-in
the past five
years. X. I. Kabachnik dealt with the influence exerted by
molecular structure
and reactivity. Ye. L. Gefter discussed the use of
organophosphorus compounds
in the industry of high-polymer compounds. X. Ya. Mikhellson, E.
V. Zeymall,
and N. K. Pruyentov spoke about the chemical mecRanism of the
interaction be-
tween organop-H-55-p-Forus compounds and cholineoterases. Problems
of the tauto-
merism of organophosphorus compounds were discussed by T. A.
lastryukoval
S. T. Ioffet V. S. Vinogradov , and V. A. Gilyarov. A. V.
Kirsanov, N. N. Nell-
Rikov, I. F. Lutsenkop A* N. Pudovik, G. Kh. Kamay, B. A.
'Arbuzov, V. S. Abramovj
and A. I. Razumov spoke about; synthetic research concerning the
preparation of
organic derivatives of varioiis, types. The lectures held by V. V.
Korshak,
M. 1. Kabachnik, T._Ya. XedvedO, G. Kh. Kamay, Ye. V. Kuznetsov,
Gals Vinokurovap
Card 1,13

The Chemistry of Organophosphorus Compounds and Their
S/030J60/000/03/033/044
Use B015/BO07
G. S. Kolesnikovp P. I. Saning A, I. Kreahkovs M. G. Voronkovq L.
A. Kroraohey
S.I. Sergiyevsk!Lya, L. Kh. Protsenkop and N. P. Grechkin were
devoted to prob-
lems of the synthesis of organophosphorus compounds which are
capable of poly-
merization and polycondensation. V. A. Yakovlev, Yu. S. KoRan. I.
A. Prankova
G. F. RzhevskMS, 1. V. Zaikonnikovay and L. S. 1fonskay reported
on the re-
search of the interaction between the chemical structure and
biological activity
of organophosphorus compounds. ff. K# Fruyeatovq V. N. Asekritovaq
~. V.
Mozhukhina, 1. M. Rakhmatulling and V. X. Sirotkin spoke about the
influence
exercised by organophosphorus (iompounds upon nervous-muscular
transmission. The
lectures delivered by V. M. Kraanovaq Z. M._Osipova, and G. I.
Timi.nskaZa dealt
with.the use of organophosphorus compounds for treating glaucoma.
L. V. Chugunova
and N. A. Korchagina explained the use of such compounds for the
preparation of
birth-stimulating agents. I. D. Neklesova spoke about the
treatment of experi-
mental trichophytosis of animals. A. K. Voskresenskaya's lecture
dealt with the
research of the "cholinergic" system of insects and with the
mechanism of in-
seoticidal action of organophosphorus compounds. Data on the
biological action
of organophosphorus compounds on peaty plantsy and soil microflora
were given
by A. M. Alekseyev. F. V. Bazonov and Ye. N. Kozlova held &lecture
on the use
of these compounds for protecting corn and cotton. The resolutions
adopted by
Card 2/3

.or
The Chemistry of Organophosphorus Compounds and Their
S/030/60/000/03/033/044
Use B015/BO07
the Conference emphasized the great importance of the chemistry
of phosphorous
high-molecular compounds. It mras found to be neoessary to
convene conferences
on the chemistry and use of organophosphorus compounds every
three years. It
was recommended to extend rescitarch work in the field of
biochemistry, physio-
logy, and toxicology of organophosphorus compounds.
Card 313

ARBU B VINOORkWU, V.S.; POLIZUYVA, N.A.
Asters of lb-katopboaphonic &aide. Report ND.5s
Structure of
the products of the interaction between certain
ot-halo ketones
of the,carbocyclic series, trietbyl phosphite. and
sodium diethyl
phosphite. I4v.AN SSSR Otd.khim.nauk no-5:832-841
My l6o. (KM 13:6)
1. Kbimicheakiy inatitut imeni A.M. Butlerova
Kazanskogo
gosudarstvennogo universiteta.
(Ketones) (Phosphorous acid)

S/062/60/000/006/017/025/xx
13020/BO60
AUTHORS: Arbuzov, B. A. and Zoroastrova,~ V. M.
TITLE: Synthesis of Phosphinic Acid EsterslContaining
Heterocyclic
Radicals. Communication 6. Interaction of Phosphorous
Acid Esters With EurEifurole,lPyromucic Acid, and Furyl
Acrylic Acidl
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheakikh nauk,
19609 No. 6, pp. 1030-1034
TEXT: Papers by G. Kamay and V. A. Kukhtin (Ref. 1) have shown
that
neutral eaters of phosphorous acid are added to
a9p.-unsaturated aldehydes,
giving rise to phosphinic acid eaters. Conjugate systems with a
larger
number of double bonds were expected to be likewise capable of
a similar
addition. Similar systems are found in al-dehydes and acids of
the furan
series. By the addition of trialkyl phosphites thereto, one
obtains eaters
of phosphinic acids with substituted furan or dihydro furan
radical. On
heating triethyl phosphite and triisopropyl phosphite with
furNrole ai
Card 1/3

Synthesis of Phosphinic Acid Esters S/062/60/000/006/017/025/XX

Containing Heterocyclic Radicals. B02O/BO6O

Communication 6.
Interaction of Phosphorous

Acid Esters With Furfurole, Pyromucic
Acid,

and Furyl Acrylic Acid

1600 the phospbite was oxidized to
phosphate, namely by the oxygen of the

aldehyde group. Small
amounts of difuryl ethane were separated from the

reaction
products for a melting point of 100 - 1010. Trialkyl phosphite

thus behaves as an oxygen acceptor and takes this oxygen from
the

aldehyde group. The interaction of triethyl phosphite with
benzaldehyde

under more rigorous conditions was experimentally
observed. Also in this

case, apart from the addition product of
triethyl phosphate to the

aldehyde group, the reaction described
by V. S. Abramov (Ref. 2) yielded

trialkyl phosphate and small
amounts of stilbene for a melting point of

124 - 1250. The oxygen
removal by means of phosphite, described in the

article under
considerations has an analogy in the removal of sulfur from

mereaptans and disulfides (Refs. 3, 4). On heating triethyl
phosphite or

triisopropyl phosphite with pyromucia acid at 130 -
1600, ethyl- or

isopropyl esters of pyromucic acid were separated
from the reaction

products. The course of the reaction between
triethy.1 phoaphite and furyl

Card 213

Synthesis of Phosphinic Acid Esters S/062/60/000/006/017/025/XX
Containing Heterocyclic Radicals, B02O/B06O
Communication 6. Interaction of Phosphorous
Acid Esters With Farfurole,.Pyromuoic Acid,
and Furyl Acrylic Acid
acrylic acid has a complicated character. Separated were diethyl
phosphorous acid, ethyl ester of furyl acrylic acidq and a product.
identified as the addition product of triethyl phosphite to furyl
acrylic
acid. The reaction of triethyl phosphite with furfurole was
performed in
Arbuzov's flask. The individual-reaotions,.the prodacts, and their
characteristics are described, There are 5 references: 2 Soviet and
3 US.
ASSOCIATION: Naucbno--iseledovatel2skiy khimichepkiy institut im. A.
M.
Butlerova Kazanskogo universit6ta (Scientific Research
Institute of Chemistry imeni A. M. Butlerov of Kazan'
University)
SUBMITTED: October 12, 1958
Card 3/3

S/062/60/000/006/021/025/xx
B02O/BO60
AUTHORS: Arbuzov, B. A. and Nikitina, V. I.
TITLE: Addition of Carbon Tetrachloridelto Divinyl and
PiperylenO
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheskikh nauk,
19609 No. 6, pp. 1131-1133
TEXT: Carbon tetrachloride has been earlier found to be added
to olefins
under the action of peroxide catalysts or ultraviolet light.
The authors
carried out experiments with the addition of carbon
tetrachloride to
divinyl and piperylene in the presence of benzoy'j- peroxide.
Butadiene was
heated with CCl4in the autoclave to 120 - 1300, which resulted
in an
appreciable resin formation. Three principal products and a
small amount
of a further product of composition C5H4C12 were found, the last
mentioned being formed by the separation of twb HCI molecules
from the
addition product CC]. butadiene. The principal products are
1.19195-
tetrachloro pentene-I -and 1',1,1,9-tetrachloro
nonanediene-397, 'the
structure of which was proved.
1-chloro-4-methyl-5,5,5-trichloro pentene-2
Card 1/"
4

Addition of Carbon Tetrachloride to S/062/60/000/006/021/025/Xx
Divinyl and Piperylene B020/BO60
is formed on the addition of CC14 to piperylene. The addition of
CC14 to
divinyl and piperylene thus takes place in the 1A-Position.
There are
3 non-Soviet references: 1.US and 2 British.
ASSOCIATION: Kazanskiy gosudarstvennyy universitet im. V,. I.
Ullyanova-Lanina (Kazan' State University imeni V. 1.
___Ll~-yanov-Lenin)
SUBMITTED- November 21, 1959
Card 2/2

12-66, QS7 006gj~60/000/008/019/033/XX
B013/ 055
AUTHORSi B. A. and Dianova (Ukhvatova), E. N.
TITLE: 2-Cyclopentenyl-l-phospbinic Acid Esters and Some DerivatiNes
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdoleniye khimicheakikh
naukp
1960, No. 8, pp.
TEXT: The effect of trialkyl phosphites and sodium dialkyl
phosphites on
3-chloro 1-cyolopentene was studied in the present paper. Treatment
of
3-chloro 1-cyclopentene with triethyl phosphite did not yield the
desired
resslt: The reaction did not take place at lower temperatures, while
at
120 C oycloperxtadiene formed.in quantitative yield by elimination
of hydro-
gen chloride. With triethyl phosphitev the latter gave ethyl
chloride and
diethyl phosphinie acid. The reaction of 3-ohloro 1-cyclopentene with
sodium diethyl phosphite, however, gave the expected cyclopentenyl
phos-
phinic acii eater. By similar reactions, other asters of
2-cyclopentenyl
1--phosphinic acid were obtained. These eaters are readily oxidized
by
acetyl hydroperoxide with formation of the corresponding oxides. The
oxidation of the 2-cyclopentenyl 1-phosphinic acid n-butyl and
isobutyl
esters by aoetyl hydroperoxide, gave besides the oxides also higher-
Card 1/2
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WAL

ARBUZOV~, B.A.- OVAs, D.Kh.
- A. _-YMUMM
Organophosphoruo derivatives of phenothiazine. Izv.AN
SSSR.Otd :8)
khim.nauk no.8:1405-140S Ag 162. NM 15.
I* MUnicheskiy institut im. A.Ye.Arbuzova.
(Phenothiazine) (Phosphorus organic compounds)

84851
S/062/60/000/010/004/018
5 no BO151BO64
AUTHORS; Arbuzov, B. A. and Yarmukhametova. D. Kh.
TITLE. Synthesis of Heterocyclic Compounds With Phosphorus in the
Cycle. Information 1. Synthesis of the Derivatives of Oxa-
and Dioxaqxy~oyhosj2horln.ane
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheskikh nauk,
1960, No. 10, PP. 1767-1771
TEXT: Data are given on the synthesis of phosphinic acid
derivatives
that are analogous to the lactones, with the intramolecular
cyclization
being carried out by esterification. In the reaction between
&-bromobutyl
acetate and triethyl phosphite, the diethyl ester of
(4-acetoxybutyl)
phosphinic acidt'was obtained:
1. 1--, OC2H5
CH3COOCH2CH 2CH2CH 2P (I)9 andp in a lower yield, also the
0 -OC H
0 2 5
Card 1/4

Synthesis of Heterocyclic Compounds With
Phosphorus in the Cycle. Information 1.
Synthesis of the Derivatives of Oxa- and
Dioxaoxydophosphorinane
4-acetoxybutyl ester of this acid;
CH3COOCH2CH2CH2CH2-?-OC2H5 (11).
I
84851
S/062/60/000/010/004/018
B015/BO64
CR3COOCH2CH2CH 2- CH~O
Heating (in the presence of a low amount of phosphoric acid as a
catalyst) causes a cyclization under the action of 8-bromobutyl
acetate
upon the diethyl ester of ethyl phosphinous acid; thus, the ethyl
ester of
(4-acetoxy ~utyl)phosphinic acid:
0
CH -CH -P-C H
2 2 \ 2 5 (IV) is formedq and by splitting off ethyl acetate from
I 0C H
CH 2- CH2 OCOdH35
the latter, 6-oxa-l-ethyl-l-oxydo-i-phosphorinane is obtained:
Card 2/4

84851
Slynth'esis of Heterocyclic Compounds With
S/062/60/000/010/004/018
Phosphorus in the Cycle. Information 1. B015/BO64
Synthesis of the Derivatives of Oxa- and
Dioxaoxydophosphorinane
0
CH -CH'-P-C H
1 2 2 1 2 5 (V). By the action of triethyl phosphite and the
CH 2-CH 2-0
diethyl ester of ethyl phosphinous acid upon the methyl
chloride of
P-acetoxy ethyl ester, the esters (VII) and (VIII) of the
corresponding
phosphinic acids were obtained in the same way. By splitting
off ethyl
acetate from (VII),
3,6-dioxa-l-ethoxy-l-oxydo-l-phosphorinane (IX) was
obtained, and by splitting off ethyl acetate from the second
ester (Viii)'V~
3,6-dioxa7l-ethyl-l-oxydo-l-phosphorinane (X) was obtained.
Table 1
gives the constants of the phosphinic acid esters, and Table
2 the
constants of the cyclization products. The course of
preparation is
described for each of the substances. There are 2 tables and
9 references:
3 Soviet and 6 US.
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84852
QT0 %1 11 Tit 11 S/062/60/000/010/005/018
B015/Bo64
AUTHORS: Arbuzov, B. A., Vinogradova, V. S., and Zvereva, M. A.
TITLE: Esters of O-Ketophosphinic Acids~ Information 6. Products
of
the Reaction of Chloro anS -Bromo Acetone6lWith the Diethyl
Ester of Ethyl P n us ACIT'-
hosphiA and With the Sodium Salt of
the Monoethyl Ester of Ethyl Phosphinous Acid
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheskikh nauk,
1960, No. 10, PP. 1772-1778-
TEXT: The investigations mentioned in the title were carried out
to
~,',etermine the effect of an exchange of an ethyl radical
directly bound to
phosphorus for the ethoxyl radical in triethyl phosphite, or in
diethyl
phosphorous sodium. The reaction between chloroacetone and the
diathyl
ester of ethyl phosphinous acid led to the mixed ethyl
isopropenyl ester
of ethyl phosphinous acid:
Card 4

84852
Esters of P-Ketophosphinic Acids. Information
S/062/6o/ooo/olO/005/016
6. Products of the Reaction of Chloro- and B015/BO64
Bromo Acetones With the Diethyl. Eater of
Ethyl Phosphinous Acid and With the Sodium
Salt of the Monoethyl Ester of Ethyl
Phosphinous Acid
/,CH
2
C H P CH (1). Two products resulted from the reaction of
2 5 \0 C2H 53
bromo acetone with the diethyl ester of ethyl phosphinous
acid, and it
was found that one of them corresponded to ester (I), and
the other
product was a mixture yielding two substances after
distillation, one
representing the ethyl ester of ethyl acetonyl phosphinic
acid,
0
it 0C2H5
C2H5 - P '--CH 2- C-CH3 (11), and the other following one of
the two
11
0
formulas:
Card 2/

Esters of P-Ketophosphinic Acids. Information
6. Products of the Reaction of Chloro- and
Bromo Acetones With the Diethyl.Ester of
Ethyl Phosphinous Acid and With the Sodium
Salt of the Monoethyl Eater of Ethyl
Phosphinous Acid
84852
S/062/60/000/010/005/018
B015/BO64
0 0C H 0 0C H
ff ,,- 2 5 If --*' 2 5
C2H5-' ~' O-C :~--CH2 (IV) or C2H5 -P '~~O-C CHBr M.
'--ICE2Br CH3
It is, howeverp necessary to oarry out further investigations to
verify
one of the two last-mentioned formulas. The reaction between
chloro
acetone and the sodium salt of the monoethyl ester of ethyl
phosphinous
acid leads to the ethyl ester of ethyl epoxy isopropyl
phosphinic acid:
OC H CH
1 2;A5,~- 3
C H -P-C-CH (VI). The Raman spectra (obtained from an Hr- -51
2 5 11 \1 2
0 0
Card 3/y

5106 6010001010102810311XX
B004YBo6o
'L"I?ORS: Arbu and Yarmukhametova, D. Kh.
T": Synthesis of Some Esters of Thiophosphoric Acid
R'-,O--fICAL-. Izvestiya Akademii nauk SSSR. Otdeleniye
khimicheskikh nauk,
1960, No. 10, pp. 1881-1883
The authors attempted to obtain.insecticides and physiologically
act4ve esters of thiophosphoric acid. Six
0,0-dialkyl-S-earbalkoxy methy
thiophosphates were syntfiesized. The following reaction scheme
is given:
( ONa
RO),POH + Na PONa; ONa + S P
4 --> (RO) 2 (RO)2P (RO)2 zz~s
(RO) P*-' ONa +HaACH R, --> (RO)y / SCH 2R, ; R - or n
2 ~~S 2 \'~-O 02H5; C3H7' C4H9;
COOC H - COOCH or CN. The following synthesis is described for
diethyl
2 5P Y
:ax't-:Ihoxy methyl thiophosphate: one hourof heating of sodium
diethyl phos-
~-'i
in benzene solution 'with sulfur; addition of bromo acetic
ester drops
(w the salt precipitate; two hours of heating, filtering off,
evaporation of
1/2

Zynthesis of Some Esters of Thiophosphoric Acid
S/062/60/000/010/028/031/XX
B004/BO60
benzine, and distillation in vacuum. Raman spectra and infrared
absorption
spectra of the compounds: (C H --' SCH2COOC2H5 and (C H
"SCH.C00CH 3
2 50)2p4l~ 2 50)2p~'~
0 0
were taken. Both compounds exhibited intensive infrared
absorption bands at
126o - 1266 cm-1, which are cha 3acteristic of the Pi-O bond. The
Raman spec-
trum showed no lines at 600 am- , that M ht point to a P=S bond.
Both in
the said two compounds and in (C _~IACH2'ONV an insecticidal
effect was
2 50Y",tO
established. Acaricidal and antiglaucomatous effects of resulting
esters
are still being examined. A paper by M. I. Kabachnik is
mentioned. There are
1 table and 2 Soviet references.
ASSOCIATION: Khimicheskiy institut im. A. Ye. Arbuzova Kazanskogo
filiala.
Akademii nauk SSSR (Chemical Institute imeni A. Ye. Arbuzov
of the Kazan, Branch of the Academy of Sciences USSR)
SUBMITTED: March 11, 1960
Card 2/2

ARBUZOV.-il-A-1-I.-JIliOGRA-DOVA, V.S.; ZV3UVA, M.A.
Raters of keto phosphonic acids. Report No.?: Products of the
reaction of,*-chlorocy0lobexanone with diethyl eater of
ethylpbos-
pbonous acid and the sodium salt of the monoethyl eater of
ethylphosphonous acid. Izv. AN S.SSR.Otd. khim. nauk no.11:1981-
1984 N 160. (MIRA 13:11)
1. Xhimicheakiy inqtitut Yo;anskogo filiala AN SSSR i
Khimicbeekiy
institut im. A.M.Butlerove, Kazanskogo universiteta im.
V.I.Ullyanova-
Lenina.
(cyclohexanone) (PhoophonouB acid)

-MIIZQY, B.A
,,. akademik; ISAYWA, Z.G.; RATMM, V.V.
Products of the autoxidation of AS -carene. Dold. AN
SSSR 134 no-31
583-586 3 160, (MMk 13:9)
1,. Nauchno-isoledovateliskiy khimicheokiy institut im.
A,M. Butlerova
prL Kazanskom gosudarstvennom universitate im. V.I.
Ullyanova-Lanina.
Oameni)
#I

ARBUZOV9 B.A,; ZORASTROVA9 V.U.
Esters of phosphoric and thiaphosphoric acids containing betero-
,cyclic radicals. Report No. 3: Compounds with tetrahydrof~,-rfuryl
radicals. Izv. AN SSSR. Otd. khim. naxic no. 1:51-55 ja 1.51.
(MUZA 14:2)
Is KhAnicheskiy institut im. A.M. Butlerova Nazanskogo gosudarstvon-
nogo universiteta im. V.I. Ullyanova-Lenina.
(Phosphoric acid) (Furfuryl alcohol) (Phosphorous acid)