SCIENTIFIC ABSTRACT YAGUPOLSKIY, L.M. - YAGUPOLSKIY, L.M.

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• Collection: Scientific Abstracts
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• Document Creation Date: November 2, 2016
• Document Release Date: March 15, 2001
• Sequence Number: 6
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

YLGTJPOLISKIY, L,M,; VISHNEVSUTA, G*O.; YAVORSKIY, D.F#;-GRUZ, B.Yee;
-------- 19=11CEM, A.S..; KHASKIN, I.-G.; GONSETSUIA, Ya.T.'- KIPRIANOVO
A.I.
Improvement in the method for producing p-nitrophenylehloro-
methylcarbinole. Ned.promo 13 noo3:20-21 Mr '59.
(MIRA 12:5)
1. I-r-stitut organicheakoy khimii AN USSR-i Kiyevskiy khimiko-
:esi4;EN-b'6*tl~,-h6,Bki7 zavod Imeni M.V.Lomonosova.
.(METHANOL)

AUTHORS: YaguPol skiy, L. M., Marenets, M. S. SOV/79-29-1-58/74
TITLE: Synthesis of the Derivatives of Phenyl Trifluoro Uethyl
Sulfone (Sintez proizvodnykh feniltriftormetilsul'Iforia)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr It
pp 278 - 283-(UScR)
ABSTRACT: It was the aim of the present study- to prep&re the ls~terwndiate
products for.the synthesis of azo- and cyanine dyes Which
contain a trifluoro methyl sulfonyl group. 3-amino-4-fluoro-
and 3-amino-4-chloro-phenyl trifluoro methyl sulfones were
obtained according to the mentioned scheme 1. From 3-nitro-
4-chloro-phenyl.trifluoro methyl sulfone by means of sodium
methylate 3-nitro-4-methoxy phenyl trifluoro methyl sulfone
was produced which was reduced to the amine
so 2CP3
if 'El
2
0011
(A).
3
Card.1/2 Apart from this the following substances were synthesized-

Synthesis of the,Derivatives of Phenyl Trifluoro Methyl SOV/79-29-1-58/74
Sulfone
2-methyl-6-trifluoro methyl 6ulfonyl benzimidazole, 2-5-tri-
f lu.oro metbyl sulfonyl berizthiazole according to schrme 2.
The latter base was transformed,into the quaternary salt
from which carboxy anine and the dye styril were obtained.
The group CP SO inposition 5 of the benzthiazole nucleus
31 2
as well as other electronegative substituents in the same
position (110 2' CF3Refs 1,2) almost.does not cbenge the'ab-
~sorption maximum of thiacarbocyanine. In the dye styril the
group CP SO shifts the absorption maximum to 25 mg towards
3 2
the side of long waves (Table). 3-nitro-4-hydrazine phenyl
frifluoro methyl.sulfone-wab"Mso obtained. There are 1
table and 9 references, 5 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Acade7,jy of Sciences,
Ukr SSR)
SUBMITTED: November 25, 1957
C ar d2/2

AUTHORS; Yagupollskiy, L. M., Troitakaya, V., I. sov/79-29-2-42/71
..TITLE: Fluor-containing Trichloro-pl~osphazo-sulfonaryls and Their
Detivaiives.(Ftori3oderzhashchiye.tri.k-,blorf.osfazosullfonarily
i:ikh proizVodny'ye)
PERIODICAL: Zhurnal obahchey khimii, 1959f Vol 29, Nr 2, pp 552-556 (USSR),.
'ABSTRACT: At present-several active insecticides with fluorine atoms in
the.molecule (Ref 1)* are.known.-Preparationsp simultaneously
containing fluorine and.phosphorus atoms arelof special inter
est.,The.synthesis.and-linvestig4tioii of'.trichloro-phosphazo-
sulfonaryls and their derivatives for such insecticidea as
-contain fluorine atoms or trifluoro-methyl groups as substi-
-in the aromatic n cle -e aim of the present
tuents U us are th
article. Por this purpose? the n-fluoro-benzene-sulfamide
(Ref 3) and the hitherto tinknown m-trifluoro-methyl-phenyl-
sulfamide were synthes-~zed. The latter was obtained according
to the scheme
Card 1/3

Fluor-containing Trichloro-phosphazo-sulfonaryls'- SOV/79-29-2-42/71
and Their Derivatives
CF CF F CF
F
3 3 3 3
U 3 03
-so Ila w_so Cl -so NH
2 2 2
Its structure was proved by transformation into m-carboxy-
benzene-sulfamide, (Ref 4) with sulfuric acid. By reaction
with PCl the sulfamides thus obtained yield trichloro-
5
phosphazo-sulfonaryls,(Ref 5):
Ar-SO2NH2 + PC1 ~b- Ar--SO2 N=PCl 3' where Ar=rr-FC6H (I)q and
4
M-CF 3C6H (II). Prom:(I),and (II) the dichloro anhydrids and
4
the correspondin g phenyl*sulfonamide-phosphoric acids were
obtained by hydrolysis and acidolysis. Also the monochlora
anhydrid of fluoro-phehyl-sulfonamide-phosphoric acid
(Scheme 5) was separated. With alcoh6lates and phenolates
Card V3 the compounds (I) and (II) condense to ether (Tables 1,2).

50). 90V/79-29-4-58/77
AUTHOR: Yagupol'Bkiy, L. M.,

TITLE: Cyanin Dyes Containing F uorine (Tsianinovyye krasitelij soder-
zhashchiye.ftor)..VI. Synthesis of Cyanin~Dyes From 5-Trifluo-
mf)thoxy-6-acetylaininobenzothiazole (VI. Sintez tsianinovykh
krasiteley iz.5-triftormetoksi-6-atsetilaminobenztiazola)
PERIODICAL: Zhurnal o Ibahchey khimii, 1959, Vol 29, Nr 4, PI) 1312-1315 (USSR)
ABSTRAM -In the previous paper (Ref I)Ithe synthesis of thiacarbocyanins
containing trifluomethoxy groups as sabstituents in Positions 5;
and 6 of the benzothiazole nucleus was described. The intro-
duction of methoxy groups j,nto the 5,5'-positions of 6,61-disub-
stituted thiacarbocyanins is known to cause an additiVe shift of
absorption maximum of-the dyes toward the long'-wave range of the
spectrum. It was interesting to,find out in what way the tri-
"fluomethoxy gr,oups-.Introduced into.positions 5,5' would in-
fluence the absorption maxir~a of 6,61-disubstiltuted thiacarbo-
cyanins. :The initial. material used f or ~.the synthesis, of these
dyes was the ether (I)_, which was obtained from a mixture of the
nitroacetylamino,deriva,tives (Ref 1). The structure of
relevant
~Card 1/3 .
this ether w" proved by removing the acetyl from it and re-

SOV/79-29-4-58/77
Cyanin Dyes Containing Fluorine. VI. Sy-,~thefjis'of Cyan-4n-Dyes From 5-Trifluo-1
Methoxy-6-acetyl.a:zinobenzothiazole
d.ucing,itl.to thediamin6which, like the other paradiamines, ex-
hibited an inten.Be.indam-ne reaction with iron trichloride. Like
the corresponding me-thoxy I derivative (Ref 3) it,was easily
oxidized to the p-quinone (Scheme 1). Compound.(I) was trans-
formed into a benzothiazole (IV) according to reference 1
(5cheme 2). By diazotizing.the amine (IV) and substituting other
groups new bases were obtained, viz. 6-chloro-, 6-iodo-, and
6-methylmercapto-5-trifluomethoxy-2-methylbenzothiazoles, which,
in turn,.were transformed into the quaternary,salts and thia-1
carbocyanins. The absorption maxima of the synthesized cyanin
dyes in alcohol are given in the table where for,comparatilte
purposes, the absorption maxi.ma of the corresponding dyes with-
trifluomethoxy groups are also given. Therefrom it may be
concluded that,the trifluomethoxy group in the 5,51-ppaitions of
the benzothiazole nucleus has a-slight effectonly - on the ab-
sorption maxima of the dyes containing weakly electropositive
::substituents in:the 6,6r...;positions. There are 1 'able and
et references.
I Sovi
-Car
d-2/3

-7i'

i~AVTHORS: Yagap6llski jroitskaya, V. I. SOY/79--29-7-68/83
W4
TITLE: Cysnine Dyes Containing Pluorine (Tsianinovyye krasiteli, soder-
zhashchiye ftor). VII. Synthesis of Cyanine Dyes From
'
6-Trifluoro-methyl and 6-Trifl-aoro-methyl-sulfonyl-
benzimidazole
(TIL Sintez ';osianinovykh krasiteley iz 6-triftormatil- i
6-~briftormetilaullfonilbe=itjidazola),
PERIODICAL s Zburnal obshohey khimiii 1959, Vol 29, Irr 7, pp 2409-2416 (USSR)
ABSTRACT: The oyanine dyes, derivatives of benzimidazolep are but little
iiivestigbted with some exceptions (Refs 1-5)- The simplest dye
oT this series, the 1,1',3,31-tatramethyl-imidocarbo cyanine
iodide (formula on page 2409) was first synthesized by Ogata
('Ref 1) and then by A. I. Kiprianov (Ref 2). The purpose of the
present paper was the synthesis of the imidocarbo cyanines which
have as substituents electrophilic trifluoro-methyl groups and
I;rifluoro-me.thyl-sulfonyl groups. The necessary derivatives of
benzimidazole.were obtained according to scheme 1 and the
Aluaternary salts from these bases,(Formula 2). h-om the
quaternary salts the cyanine dyes viere synthesized, formula and
absorption maximaof which are presented.in tables I and 2. The
Card 1/3 symmetrical imidocarbo cyanine dyes were obtained by boiling the

- - - -- - - - - -
Cyanine Dyes ContEdning Fluorine. VII. Synthesis of SOV/79-29-7-68/83
Cyanine Dyes From,,6-Trifluoro-methyl and,6-Trifluoro-methj -sulfonyl-
.benzl~iidazole
qu aternary-salts with orthoformio acid in nitro-benzene
according to A. Van Dormael (Ref 6). The introduction of the
txifluoro-metbyl group and trifluoro-methyl-sulfonyl grcrxp
(Ref 8) into the benzthiazole nucleus of the thiacarbo-eyanine
hurdly -changes. the absorption maximum of the dye. Table 2 gives
formulae and absorption maxima of two unsymmetrical cyanine dyes
and two rhodocyanines. The substitution of ethyl radicals for
radicals on the'nitrogen atoms of the benzimidazole
the methyl
l
nucleus causes considerable changes in the absorption maximum
of the imidocarbo cyanines. The synthesis of 2-mothyl-3-phenyl-
6-trifluoro-mIethyl- and 2-methyl-3-et~yl-6-trifluoro-methyl-
fiulfonyl-tenzimidazole was thus described. These bases, like
~,he 2-mothyl-3-ph6nyl-6-trifluoro-ethyl-sulfonyl-benzimidazole
previously described, were then.transformed'into quaternary salts
from which 8 symmetrical imidocarbo cyanines, 2 unsymmetrical
band 2 rhodocyanines were obtained. There are 3 tables and
.12-references, 6 of which are Soviet.
Card 2/~

50)
AUTHORSt Ysigupol I skiyt L. W., Troitskaya, V. If 'SOV/79-29-8-63/81
TITLE: Cyanin Dyes Contgihing Fluorine. VIII. Synthesis of Cyanin Dyes
Pj~
()m 496-Bis-(triflu6romethyl))-4-chloro-6-trifluoromethyl and
,
4--(Iohloro-6-trifluoromethylsulfonylbenzimidazole
PERIODICAL: Zhurnal obahchey khimiio 1959, Vol 29, Nr 89 pp 2730-2736 (USSR)
ABSTRACTz In a previous paper (Ref 1),the.synthesio of imidocarbocyanine
containing as substituents in position 6 of the benzimidazole
nucleus trifluoromethyl- and trifluoromethylsulfonylgrOUPB was
described. In the present paper tetrasubstituted imidocarbocyanins
of the general.formula (A) were~obtained. The benzimidazole
derivatives which were used an initial products and the quaternary
salts were synth,eei-zed according, to the already deBoribed method.
(Ref 1). Table I gives formulas'and absorption maxima of the
Symmetrical dyes in alcohol. By way of-comparisonthe absorption
ma,xima of the corresponding dyes which do -not contain substituents
in position 4 of the benzimidazole-nucleus are also given. As is
Ecien from the data of table 11 the introduction, of trifluoromethyl
groups into positions 4,41 of 6g6-bis-(trifluoromethyl)-imido-
'
Card 1/2 carbocyanin (dye's I III),causes a
shift of the absorption

Cyanin Dy .es lontaining Fluorine. VIII. Synthesis of BOV/79-29-8-63/81
Cyanin Dyes From 4,6-]3is-(trifluoromethyl).,-4-chloro-6-trifluoromethy1 and.
4-.Chloro-6-trifluoromethylsulfonylben:.imidazole
maximum towards the long waves of about 11 13 m/,(/ the
introduction of the chlorine atom into the same positions a
shift Of Only 4 m dye IV) and a shift of-about 3 - 6 m
,,Ze, i n
the direction of -6u,-6~-bis-(trifluoromethylsulfonyl)-imidocarbo-
oyanin (dyes V-VII).-Table 2 gives formulas and absorption maxima
of the 4 asymmetrical oyanin dyes. Tables 3 and 4 give the yield
and melting,points of symmetrical and asymmetrical dyes. There
are 4 tables and 5 referencest 3 of which are Soviet.
ASSOCIATIONt Institut organicheekoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences of
the Ukrainskaya SSR)
SUBMITTED: July 10, 1958
Card 2/2

5(3) SOV/79-29-9-60/76
AUTHORS: Yagupollskiyj L., M., Fialkov, Yu. A.
TITLE: Naphthalene and Its Derivatives
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 9, PP 3082-30 66(USSR)
ABSTRACT:. The trifluoromethyl derivatives of naphthalene have hitherto
not been investigated. The synthesis of 1-trifluoromethyl
naphthalene briefly mentioned.in an American patent (Ref 1)
is very insufficiently described, i.e. no constants and no
exact course of synthesis both.of the.final product and
of 1-trichloromethyl naph;halene as initial product are given.
The trichloromethyl derivatives of naphthalene are difficult-
ly accessible (Ref-2). In the experiment made by A. H. Nesmeyanov
and co-workers (Ref 3) to obtain a-trichloromethyl naphtha-
lene, by.thermal decomposition of the copper oxide salt of
trichloroacetic acid in an excess amount of naphthalene it
could not be separated. For this reason the o-chlorotrichloro-
methyl derivatives of naphthalene which were obtained from
the corresponding oxynaphthoic acids with PC1 were used as
5
initial products for the synthesis of the trifluoromethyl com-
Card 1/4 pounds of the naphthalene seriese From the three o-oxynaphthoia

SOV/79-29-9-60/76
2-Trifluoroinethyl 17aphthalene and Its Derivatives
acids, R. Wolffenstein (Ref 4) succeeded in transforming
only I-oxy-2-naphthoic:acid into 1-chloro-2-trichloromethyl
naphthalene; the yield is not specified. The remaining acids
could be identified only in the form of the corresponding
o-chlo.ronaplthoic acids. The authors repeated Wdffenstein's
experiments. They.succeeded in synthesizing 1-chloro-2-tri-
chloromethyl naphthalene from 1-oxy-2-naphthoic acid in a
yield of 35%. The replacement of chlorine by fluorine in
1-chloro-2-trichloromethyl naphthalene with SbF in the
3
-e of SbCl and without the latter gave no positive
presenc
5
results. The fluorination of 1-chloro-2-trifluoromethyl
naphthalene succeeded only in solvents. In chlorobenzene a
yield of 90% of 1-chloro--%trifluoromethyl naphthalene was
obtained. 1-chloro-2-trifluoromethyl naphthalene was trans-
formed, on heating with copper cyanide in the presence of
pyridine,into the nitrile of 2-trifluoromethyl-1-naphthoic
Card 2/4 acid from -which the amide was obtained. This amide yielded,

Naphthalene and,lts Derivatives
according to the scheme desc:eibed, 1-amino-2-trifluoromethyl
naphthalene via 2-trifluoromethyl-i-naphtboic acid according
to Hofmann. In'the.Hofmann reaction which proceeds smooth-
ly, the forming 1-amino-2-triflt,:,oromethyl naphthalene hydro-
lyzee on heating in alkaline medium. For this reason the
amino had to be-removed by distillation from the reaction
zone already at the momentof the.formation. Thusq the other-
wise low yield could be increased to 61%. By this method
the instability of the trifluoro methyl,group in I-amino-2-
trifluoromet l.naphthalene-towtirds aqueous alkali lyes was
found (Rof 7~- From the amino (VI) and a-naphthylamine (Ref 8)
the dyestuffs (A) were obtained by diazotization and coupling
with dimethyl aniline. As may be seen from the table the
introduction of the,trifluoromethyl group in molecule
of the dyestuff.(A) shifts its.absorption maximum in the direc
tion of the short waves in neutral as well.ae in acid solutions.
There Are 1 table and 9 references, I of which is Soviet.
ASSOCIATION; Institut organicheskoy khimii Akademii nauk Ukrainskoy SSR
Card 3/4 (Institute of Organic Chemistry of the Academy of Sciences

50) SOV/79-29-9-61/76
AUTHORS Shtepanek, A. S.
TITLE: Synthesis of the.Nitro Derivatives of ei-Chlorostyrene
PERIODICAL:, Zhurnal obahchey khimii, 1959, V01.29, Nr 9, pp 3086-3092
(USSR)~
ABSTRAM The, authors tried to use the easily accessible p- and m-nitro-
, phenyl.ohloromethyl carbinols (Rafe 1, 2) for the synthesis
of the corresponding nitro derivatives of 6)-chloroutyrone
by substituting the chlorine for hydroxyl with a subsequent
separation of HC1 according to do heme (A). In the attempt of
substituting chlorine in compound,(I) for hydroxyl with the
aid of thionyl chloride the already known compound (V) was
obtained instead of the expecterl compound (IT). in the action
of:PC1 on (1) compound (II)-smoothly forms, which reacts
i is (B), and
with t. ethylamine.in alcohol according to scheu
which leads-to compound (IV).,The structure of compound (IV)
was proved according to scheme 2.' m-,Ifitrophenyl chloromethyl
carbinol'(VI) which together with thionyl chloride, as men-
tioned above, gives compound (VII) reacts in a similar way
as the.para-derivative. PCl 5 transforms compound (VI) into
Card 1/3 the dichloride (VIII). In the separation of HC1 by an alcoholic

-29-9-61/76
SOV/79
Synthesis of the Nitro Derivatives of w -Chlorostyrene
solution of triethylamine an uncrystallizable oil results.
In contrast to it the earlier described (Ref 5) W -nitro-
m-chlorostyrene is a solid compound. Similar to the para-iso-
mer-the preparation obtained must have the structure of
m-nitro-a-chloroetyrone (IX). Also the hitherto undaiiaribed
315-dinitro- (X) and 2,4-dinitro phenyl chloromethyl carbinol
(XI) was synthesized by nitration of nitric acid ester of
m- and p.-.nitrophenyl.ohloromethyl carbinol with subsequent
-int t I acid medium in the presance
~saponification o s rong y
of urea." From carbinol (X) the dichloride (XII) was then obtain-
ed with:PC1 which in the separation of HCl yielded 3,5-di-
59
nitro-a-chlorostyrene (XTII). The attempt-of obtaining p-nitro-
W-chlorostyrene (III) by separating water from p-nitrophenyl
chloromethyl carbinol could be carried out best, in order
to obtain better yields, by heating carbinal ~I) with
phosphoric aci d anhydride at 100 0. The styrene ~III) yield
was 47% (besides its racemate (XIV) (4%)). By the same method
the styrenes (XV) and(XVI) resultedby separating rater from
the corresponding carbinols. Compound (XVII) was formed as
side product of the latter. It was shown that, in contrast
Card 2/3 to the meta-isomerg p-nitro-&J-chlorostyrene has a mobile

S/079/60/030/04/54/080
BOOI/BO02
AMHORS a 'i L 9 Butlorovskiyj M. kel"Belinakayai-R. V.,,
-TITLE: m- and p-Iminophenylethyleneglycolal
~PERIODIGAM Zhurnal obahchey khimii, 1960, Vol. 30, No. 4, PP- 128871291
TEXTt ~The authors converted m- and p-nitrophenylahloromethylcarbinols
(Ref. 1) which-are now easily a-iailable, into m- andip-aminophonylethylene-
glycols which may serve as initial substances' for the synthesis of dyes and
highly molecular compounds.,The synthesis:.of m- and p-nitrophenylethylene-
glycols was caused by heating of the corresponding nitrophenylehloromethyl-
carbinols with potassium carbonate dissolved in waters
N020 6H4 CHOHCH2Cl ------- >NO2C6H4CHOHCH20H. The two glycols which.are easily
9oluble,izi*,waterv were extracted with ether.or diohloroethane. m-nitro-
phenylethyleneglycol was also obtained by saponification of diacetyl
derivative (IT), according to,Soheme 2. After heatUig with 1% sulfuric
acid, the oxide of p-nitrostyrene yields p-nitrophenylei;hyleneglycol. The
hydration process of the oxide of m-nitrostyrone is-much more complicated,
Card 1/3

and p4minophenylethyleneglycols S/079/60/030/04/54/080
B001/B002
since many. by-products.develop wh ioh inhIibit the separation of m-nitro-
phenylethyleneglycol. During theoxidation of p-nitrophenylethyleneglycol
with diluted nitjio aciat p-nitrobenzoyloarbinol (III) develops which
melts at 134-135 1 P-302CO4 CHOHOH20H !p p-N02G 6H4CIOCH2OH (III). The
authors of the,present paperp In a-similar way as other scientists by othei
methods (Refs.,20), obtained the acetyl derivative of carbinol III) from"-
p-nitrochloroaoetophanon-e with the melting point also at 121-122~. The
ound obtained by Engler and Zielke thus does not co:~respond to product
I) whose melting point is 132-133 0, but to the aoetyl derivative. In Ix
M
the presence of 4.platinum cata2yot, m- aad.p-nitrophenylethyleneglycol
'was reduced into amirto compounds. High-melting,produata of unknown
structure,developed by the reduotion of p-nitrophenylohloromethylearbinol.
Azo dyes',~I*ere obtained from all amino compounds, by coupling with
P-oxynaphthoic acid. There are 3 references,_1 of which is Soviet.
ASSOCIATION; Institut organicheskoy khimii kkademii nauk Ukrainskoy SSR
(Institiate of Organic Chemistry of the Academy of_Sciences,
Ukrainskaya SSE)
Card 2/3

'7
3/079/60/030/04/55/080
0 0 BOQ1/BO02
AUTHORS j. YaguPol Iska, L. M.1 Fialkott Yu. A.
TITLEf -1 -Phenyl-2-Arif luoromethy Phenyltrifluoromethyl-
acetylene and Their Derivatives
FERIODICALt Zhurnal obahchey khimii, 1960, Vol- 30, No. 4, PP- 1291-1294,
TEXTs The authors synthesiz'ed thevinylene homolog of benzotrifluoride (I)
and the.corresponding acetylene compound (II)t G 6H 5CH - CH-OF 3 M,
C H C a C-CF- (II). The initial product used was I-phenyl-2-trichloro-
~6 9
Met Tle.thylene*(III) which was obtained by adding trichlorobromo methane
to styrene, and separating hydrogen bro:zide (Refs. 1,2). Most successful
was the. substitution of chlorine by.fluorine An compound (III) by means of
antimony.trifluoride in.dioxane, by which (I) wa's obtained in good yields.
I-phenyl-2-trifluoromethylethylene (I) easily forms addition compounds with
chlorine and bromium, and develops two diastereoisomer& which cannot be
dissolved by vacuim distill-nition. Compound (I) does not enter into the
..dienesynthe8iS, and according to Prilezhayev it does not develop an oxide
--Card 1/3

07 6 2
1-~-Phenyl-2-trifluoromethylethyleneg Phenyltri- 8/079/60/030/04/55/0610
fluoromethylao,stylene and Their Derivatives BOOI/BO02
if benzene hydroperoxide.is.added. Compound (II) was synthesized according
to, the following schemes
C H CH OHOF
6 5 3 N V1, -B
KOH~
5)31 -C H CH=m-GBrCF
4
6 5
Br Br.,_(IVY (V) (Ref a 0A,5)
~~,In, phenylt'rifluorome,thylacetylene th6-trifluoromethyl group isstable
against alkali liquor,-since.good tields of compound (II) ave obtained from
(T) by action'of melted KOH at 230 Ilhenyltrifluoromethylacetklene easf',ly
;forms.addition compounds with 2 bromium~atomsj further additions do not
take place. Four atoms of chlorine~form an addition compouhd with (II).
Unlike bis-(tiifluotomethyl)-acetyleni3 (Ref. 6),(II).does not form addition
compounds with*aoetic acid. All liquid compounds obtained are described in
the table. The absorption maxima and extinctions of (I) and (II) in alcohol
were,determined. A, similar shift of the absorption maximum towards shorter
waves was found in the comparison bettieen.ultraviolet spectra of styreno
and phenylacetylerie (Ref.,9). There are I table and 9 references, 1 of
which is Soviet.
Card 2/3

S/079J60/030/04/56/080
BOOI/BOI 1.
AUTHORSt Yagupol skivt L. Mop Yufap P*-A*
Ph -bis-( -phos ox'. e Phenyl Trichloro-
TITLE$ enyl trichloromethyl) phin d
_mkthyl PhosphinicAcid, and Their Beriv=aves
PERIODICAL: Zhurnal obshchey khimii, 1960, Vol. 309 No. 4P pp. 1294-1299,
TEXT: The authors aimed at sypthesizing compounds containing a phosphorus
atom linked.vith the benzene Ang and with one or two trichloromethyl groups.
~The oxide of vj,Lol-'dichlorodimethyl phenyl phosphine (Ref. 1), which was
chlorinated 0 150-~2150,,served as the initial product. The resulting product
was the oxide of 'hentj-bis-(trichloromethyl)-phosphine (I)
p
A1,
The
oxide of w,ol-dichloro dimethil-(p
C _'i(CH >C6Y (cc 3)
6H5 2-,,9 2.
chlorovhenyl)-phosphine, which was obtained from p-chlorophenyl tetrachloro-
-phosphorus and diazonethane, was chlohnated, and theoxide of p.-chlorophenyl-
Card 1/ 3

-180
Phenyl-bis (trichloromethyl)-.phosphinoxide, Phonyl S/079/60/030/041/56/C
Trichloromethyl Phosphinic Acid,,and Their BooliB011
Derivatives
(II) was obtained. Both oxides (I) and (II)
a:~e colorless crystalline products and do not change on the, action of
aqueous acid-,snd alkali solutions up to 1000o They are so stable that they
.,can be nitrated at 1001 with tho.nitration mixtures
Cel Ccl
O=p 3 0- 3:
7
\CCl Ccl
3 3
NO 1102
2
Cl
The ethyl ester of phenyl trichloromethyl phosphinic aeid was taken as'the
initial product of the synthesis of the derivatives of the latter (Ref, 2).
Investigations were extended to the reaction of ester (III) with PC1 52 with
the acid chloride (IV) forming according to Scaeme 2. In addition to the
Card..2/3

.Phenyl-bi6-(trichloromethyl)-pho6phinoxide~ S/07 9/60/030/04/5 6/080
Phenyl Trichloromethyl Phosphinic Ao;idl and BOOI/BO11
Their Derivatives
acid chloride (IV) there arises a certaln amount of (V)p according to
Scheme 3- On heating the ester (III) wib, 3 moles-bf.-,iPC1 a-t:'10O_i6O0j"d); V/
5
tl\complek (VI) i's formed (Scheme 4)s which) on hydrolyzing~ gives rise to the
~-acid chloride (IV) in a quantitative yield. The a4thors became acquainted with
the:article by P., Biddlep I. Kennedy ' 1. W'illans (Refa 3) only after having.
completed their own investigation (scheme 5)4 A paper by G~ Kamay is mentioned
(Ref. 2), There-are 4 references, 2 of which are Soviet-,
ASSOCIATIONs, Instit.ut organicheskoy-khimii Akademii nauk Ukraih-bkoy SSR
(Institute of Otannic chemistr.1- of the Academy of'sciences,
Ukrainskaya SSRY
SUBMITTED: May 5. 1959
Card 3/3

S/079/60/030/010/027/030
Booi~BO66
KUTHOR: Yagupol'skiy, L. M.
TITLE-. 1.1100-Tetrafluoro Phthalane and Its Derivatives
.~PERIODICAL:, Zhurnal obshchey khimii, 196o, vol. 30, No. 10,
pp- 3444 3446
TEXT: Considering the papers of Refs. 1-51 the author wanted to syn-
thesize I 100-tetrafluoro phthalane from 191 393-tetrachloro phthalane
by meanslof antimony trifluoride..In this synthesis, however, a mixture
of 1,1,3,3-tetrafluoro phthalane (I) and o-trifluoro methyl-benzoyl
fluoride (II) resulted according to the Scheme
Iccl Ccl CF CF
2 3 3
sbF
3
Ccl 10
CF
\Cl (I~ 2 (11) '-F
Card 1/3

Tetrafluoro Phthalan
1 o3,3- e and Its /079/60/030/010/027/030
Derivatives BbOlIB066
Compound (II) was converted into the amide by passing ammonia through
the solution of,the resultant mixture of (I) and (II) in petroleum
ether. T
Us amide was filtered off. 1,1 3,3-tetrafluoro phthalane, a
.
0
colorless liquid melting at 153,C, was distilled off. The question as
to whether the acid fluoride(II) is formed by iBomerization of
1,10,3-tetrafluoro phthalane or by the good isomerization of
10,30-tetrachloro phthalane to the acid chloride of o-t.richloro
methyl benzaic acid with subsequent fluorination was examined. Accord-
ing to the experiments7 the latter asnumption is
correct. It was thus
,
shown that),'~unlike the oorreaponding ohloro.derivatives,
:fluoro P1 thi
i t4ane,and o-trifluoro mothirl-banzoyl fluoride are not capable
of mutual isomerization. The author also describes the synthesis of the
5-nitro-, 5--amino-, 5-cyano-, 5-carboxy-, and 5-fluorc, derivatives of
b
10,30-tetrafluoro phthalane. The a
oorption spectra of all prepara-
tiona aro shown in throo Diagramoo 10,393-tetrafluoro phthalane Is
stable to alkaline reagents. 6-nitro-1,1,3,3-tetrafluoro phthalane could
be obtained only from 6-nitro p~thaliae. With dimethyl aniline, the re-
sultant amine gives an azo dy L5(Scheme 2). There are 3 figures and
8 references: 2 Soviet9.2 US, and 4,German.
Card 2/3

87531
7
_5/079/()Q/W!()/Q2/011 /0)
BuW 06/z
AUTHORS: ..Ya and Ivanova, Zh. M.
TITLEt p-Trif luoro- Methyl Phenyl Tetrafluora Phosphorus and Its
Derivatives
PERIODICALt Zh~urnal obshchey khimii, 1960, Vol- 30, No. 12, PP-4026-4030
TEXT3 .The authors continued their.investigation,(Refe.1,2) on the
synthesis of some aryl tetraphosphorus fluoride compounds, difluorides
of aryl- and aryl thiophosphinic acids, and tried to synthesize the
phenyl tetra,phosphorus fluoride compound with an electronegative tri-
fluoro methyl group.as substituent in the molecule, and to.test its
stability toward hydrolysis. For this-purpose, p-tolyl dichloro phos-
phine was produced, converted at a low-temperature by chlorination into
p-tolyl tetraphosphorus dichloride, and then in the presence of azoiso-
butyric acid dinitrile chlorinated in the methyl group. Chlorination did,
however, not proceed smoothly under various reaction conditions so that
no pure products were obtained. Also the fluorination of commercial
pa-trichloro methyl-Phenyl phosphorus tetrachloride and the dichloride of
Card 1/3

87531
p-Trifluoro Methy). Phenyl Tetrafluoro S/079/60/030/012/015/027
Phosphorus and Its Derivati4es Booi/Bo64
p-trichloro. methyl-phenyl phosphorus tetrachloride, as well aa the di-
chloride of p-trichloro methyl-phonyl phosphinic acid with SbF or UP
proved unsuccessful. Therefore, the authors proceeded from a compound
already containing a trifluoro methyl group when synthesizing p-trifluoro
methyl-phenyl phosphorus tetrachloride. The authors proceeded from
p-bromobenzotrifluoride, which was.converted into organo-magnesium and,
moreover, into organo-zinc compounds, and by means of PC1 into p-tri-
3
fluoro methyl-phenyl phosphine dichloride. The latter was chlorinated and
furthermore fluorinated to p-trifluoro methyl-phenyl tetrapho~phorus
tri fluoride by means of SbF3 Cl
p -CF C E Br Mg 4 P-CF C H Zn]Br ~~4p-CF C H Pcl 2>p-CF C H PC1
3 6 4 ZnCl2 3 6 4 3 6 4 2. 3 6 4 4
BbF
3
~P-CF C R PF Various derivatives were synthesized from p-tri-
3 6 4 4
f.luoro,methyl-phenyl phosphorus tetrachloride. In one of previous papers
(Ref*3) it was shown that phenyl phosphorus tetrachloride reacts with
diazomethane by the scheme C IH PCl-+ 2CH N ~PC H PC1 (CH Cl)
6 5 4 2 2 6 5 2 2 2
Card 2/3

87531
P-Trifluoro Idethyl Phenyl Tetrafluoro S/073/60/030/012/015/027
Phosphorusland Its Derivatives B001/D064
henyl phosphorus tetrachloride reacts with diazomethane less vigorous"Y.
After the reaction products.had been hydrolyzed, acrystalline acid
0
product was separated which was identified'-as 0 H F--QH i.e.',phenyl-w-
6 5
I-CH P
2
fluoro methyl.phosphinic acid*' -In.Gontrast t6 published data it was shown
that,phenyl phosphorus tetra-fluoride reacts immediately, with carboxylic
acids, under.the formation of acid fluorides. Thus., phenyl phosphorus
tetrafluoride gives propionic ti,cid.fluoride with propionic acid. In order'
to protect the glass against,'HF, however.-a salt of this acid (e.g., the
lithium salt) was used. There are 7 r4ferences: 4 Soviet, 1 US and
2 Swiss.
ASSOCIATION: Institut o:oganicheskoy khimii-Akademii nauk Ukrainskoy SSR
(Institute.of Organic Chemistry of the Academy of Sciences
Ukrainskaya SSRY
SUBMITTED: January 23) 1960
Card 3/3

A'~ I 170Z S/02o/60/134/006/021/031
~-Ji B016/BO67
AUTHORS& _Yagui) a 1ski M.
L M. and Yagapoll skm2,,--
TITLE: Electron Nature of the Fluorine-containin) Substituents
PERIODICAM
Doklady Akademii.nauk SSSR9 196.0, Vol. 1349 No. 6,
PP- 1381 1383
TEXTs The authors found that the physicochemical properties of several
aromatic fluorine compounds (except for those substituted with fluorine
atoms, and for trifluoro m9thyl derivatives of benzene) have not been
investigated. They first determined the pKof the correspon.ding benzoic
acids. For this purpose they measured the pH of the aqueous-alcoholic
solutions half-neutralized with titrated NaOH solution. The pH was
measured by means of a tube potentiometer AT-5 (LP-5) with glass
electrode at 250C. A saturated calomel electrodeserved as comparison
electrode. Table 1 gives the results of thedetermination. To deteTmine
the constant P of the equation by,L. P. Hammett (Ref. 2) log(k/k~ -T6-
the authors chose 5 aubstituents with exactly determined 6'-eonstants
and pKa of the corresponding benzoic acid,3 in aqueous ethanol. Besides
Card 1/ 3,

Electron Nature.of the Fluorine-containing S10201601134100610211031
Substituehts B016/BO67
.,they used thed'ataJor pKa.and 6' 0 of the non-substituted benzoic
acids. For calculating q only the pK, of the m-derivatives of benzoic
acid we L,
re used. On the bas4s of these data and according to the method
described in Ref- 3 it was found that. 1-535; the Correlation coef-
ficient r and the standard error B were also calculatad. The substituents
.~'ohosen by the authors satisfy R. W. Taft's conditions (Ref- 4). They werei
~H,Vm-Br, CH~CO, OF 39 CH' S02CE39 since In this case 1,635,
r - 0.9989 and s = 0-03- On the basis of 31 the.6constants of -the now
substituents in meta- and para-poq4tion were calculated. The cyclic groups
OF 0
/~ 2
0 and C11- were Ascribed to the p-series on the basis of the
".4
CF 2- "0 0
analogy with group as,well as w1th.-tetralin and hydrindene
0
(Refs.'.0 93). All.substituents mentioned are electron acceptors or very
weak electron donors. The dissociation constants of the acids mentioned
are higher than those of benzoic acid.-the values of the 6 constants
Card 2/3

84675
Electron Nature.of the Fluorilne-containing
Substituents Bo16,,Bo67
being positive. It appears from Table I that' the trifluoro methyl sulfonyl
group is the strongest electron-acceptor group among the known sub-
stituents in the benzene ring. p-trifluoxo methyl sulfonyl benzoic acid
is,more than twice as strong as p-nitr,)beuzoio acidlThis holds also for
meta acids. Fig. 1 shows the dependence wFFTIR values of the 6con.,
~stants an Id log k of substituted benzoic acids In 50% aqueous.ethariol. The
authors compared the intensity andthe orientating Gffect of some groups
and they describe.the positions in which individual compounds can be
nitratedo There are 1 figure, 1 tnble, and 8 non-Sovicet, '"eferences.
ASSOCIATIONi-, Institut organicheskoy kh-Imil Akademi-I nauk TjSSR (Institute
of organic Chemis"'ry of the Academy of SCie-aces, U~TSSR)
PRESENTEDs June 1. 1960, by V. X. Kondratlyev, Academician
SUBMITTEDs May 259 1960
Card 3/3

B004/BO56
AUTHORS; Yagupol,lskiy, L. M., Bystrov, V. F., and Utyanskaya, E. Z.
TITLE: Investigation-of the Chemical Shift of the Magnetic
Resonance of Fluorine19 Nuclei in Fluorobenzenes With
Fluorine-containing,Subutituents
..PERIODICA1: Doklady Akademii nauk,SSSR, 1960, Vol. 135, No. 2,
~pp- 377-380
,TEXT:, It was thepurpose of the present work to investigate the effect of
fluorine-containing substituents upon the electron density-distribution in
the benzene ring, and to determine theinterrelation between thestructure
of these compounds and their reactivity by means of nuclear magnetic
resonance (nmr). The shift in the ring ofmonosubstituted fluorobenzenes
caused by fluorine and referred tothe resonance values of fluorine in
nonsubstituted fluorobenzene was measured and determined from the equation:
(Hx lie 106/H H and H a re resonance values of the
H F)* C H F x C H F
6 5 6 5
Card ~1/5

of the Chemical-Shift of the S/020/60/135/002/029/036
Invoutigation,
Mape.tio'Robonano.o of,,Fluoring'. ITUO10i in, B004/BO56
Fluorobenzenes'Wi~h Pluorine-containing
Substituents
% external -magnetic field for P19 nuoloi in -the onne of substituted (X) and
nonsubstituted fluorobenzene. Apparatus and mathod of mouaromont aro
described in Ref..1. The values for S are given in Table1 for various
substituents in o-, m- and p-position. The authors discuss the data given
in publications,for the interrelation between t and the Hammett constant a,
they compare the values obtainod from various calculations, and found.that
substituents with positive conjunction effect a. cause a mota-ponition,
such with negative substitution effect, however, an ortho- or para-
'Position. Tables 3 and 4 compare the values of 8 cs for the p-position
p p
and of 9 a for meta-positioni Be idea, Tabli) 3 gives the light
m m
absorption Amax of 4'--Substitutel dimethylaminoazobenzene, which changes
-similar to the chemical shift in p-substi tuted fluorobenzenes, and
indicates the existence of uniform electron displacements. There are 4.
tables and 9 references: 3 Soviett 7 US, and 1 French..
Card 2/5.

TT Card
2
S/P 0166113510021b2910~,.;
B000056
10,

77
Legend' to
Tables 3. and 4

j 1 ~,.Substitueht,- -
j
.(in. aloohol)
Q 0
Wx-i i

c$
1
P
sd~c
N

O
CH

N CF,\

0

OCH

F
j .
, .
,
CF./. . ,

c; 4
7
-10,8
-9,6
6
-5

u
03
4
0,78 0 j.72

- 0,66 O~ 81 A
.50
. 0 ~4
/

X
~ie)
,.,, V 6 76,
475 I~
445 450 447 430

3AM

F
o$ Is

O,.
SOaCH
CN:
Cps

0 0.56 ~:0,43

fe WgNlu~ ~ll-l~~-li;~-~,?~l-."a"Oi]05-lpavl-"Nl~:,~.*L~.9t~l-t-OWILII-~fp).R4,-,--
JL
UTYANSKAYA, B.Z.; YAGUPOL'SKIY,..,-
STROV, V-1--
By
of.~19 in aromatic compounds with
Magnetic resonance spectr Opt,j spektr. 10 no. 1:138-
substittLeatB
ning 14:1)
fluorine-contai MIRA
141 ja 161.,
(11,4orlue-spectra)'

X
I

S/070JOI/031-/011-/006/015
D202/D305
AUTHORS3 Tagapoltskiyq'L. M.~ an dFim1kovq Tho A.,
TITLE: Derivatives of the -vinyl. homologue. of banzo--tri-
fluoride
PERIODICALs Zhurnalobshchey khimii~ v. 319 no* 3686-3503
TEXT% This is a continuation of previous work in 1POIlich a new compound
1-phenyl-2-tri flu o ro methylene has been found (cpd. 1). In this investi-
gationg the wthorgs aim, was to obtain the Para and meta derivatives of
the above compound. n-Bromo-otyrene gave an addition product with
CBrC13 (in Vde.presence of benzoylperoxid*), forming n-bromo-pbenyl
trichlorobromopranes BID-C H -CH-CH -CC13 a crystalline product,
6 4 2
br
m,p. 84.5 -'85.5; after the removal of HBrq n-broma-pheny.1 trich''oro-
methylene was obtainedo (Cpd. 11), an oily aubstanceg b.p. 120 121'C
Card 1/5

3/079J61/031/01.1/006/015
Derivatives of theoo
(0.1 mm) By the action of SbF3 on cpd,, II it was converted.to n-
bromo-phenyl,-trifluoro-mathylene (cpd,, 111) cryatals~ mp. gl,,5 - 22.5,
~b.p. 1150 (25 mm).. This compound heated vith CuCN formed (in pyridine)
0
romethylene MOP0 48 -~49,5
(cpd. IV) crystals,
n-cyano-phenyl-tri fluo
Compound JV was oxidized with H 0 to form u-amidt (4pd,, V) c-rystals,
2 2
mopo 189 ~- He., ~ 1~y hydrolysis of cpd. Y;~ a n-carboxy 0compound was ob-
tained (cpdo VI), a crystalline, produA., mpo 246 -, 247 . Th6 aamii zpd.
IVI vas obtained by -the action of bu!Wl 'Ll o-n cpd. 111-and.oubs.,~q)r~a-t
action of solid CO 23 m,,po 214T - 248 , The amldj~ -was v-onvertel int.,)
the n-amine by Hofmann3s method fo gi--qe~ CF,3-CK
crystalaq m'p. 62 - 83 and the n-amins'vas conyerted by tbs
action of MONO 2 and that of aodium fluo-borafA into n-flno= phenyl
2) 2.1
trifluoro methy-leney b,,p. 165 - 160 1,4625~ 4, 1"2682 (tp,i"
4
VIII)~, By diazotization and steam-distillationz V17. p-trifluoro
methylene pbenol ('IX) va-v obtained in crystalaq, m~p. 71,,5 -12.5, TD
card 2/ra

10186
S/0,19J61/031/011/006/015
D202/1)305
vatives of theo0c B-aco tamide j
Deri
s 0j cpd. 12 the autliors u ed its
repare meta_derivat~ive Impound was fo rmed? the _ ni tro-group
p nitro CO
by nitration ofIvhich the.acetemides
the ortho Position ' to cpa. X)
N11COCII
ell CH 3
C
F3_
NO
2
tion reaction formed yellow
.this, by a reduction-cyclizs, Cpd~ X
From was obtained (cpd. 209 OC~ C-pd. X9
ad M.p. of 208 - 0
lene)-benz-imidazol p , XI h lene' range-
methy P. 169 end c d -,4,.jrifluoro methYY
needles) Mo .1-nitro phenyl e M_
,lysis formed 4-&Min0-'I after desomination ga'v
after hydrc ; M.p. JW- 1210; this compojjud9 * t Of MOPO 42o6
red needleil crystalline produc
nitro phenyl trifluoro methylene dration 'with Plat'n'm blackg m-
43.60C- From the latter9 after hy tainedz
ethylene aniline was Ob
trifluoro m
Card 3/5

S/079J61 /031/011/0o6/0115
D202/1)30
Deri-vetives of thecoa
M.p, 29o5 and from
CF _C11 CH
3
N112 liquid of bopo ad, (0.2 mm).
101 (cpd. XIII), an oily' riflUorg g!roUp Of
Fonding Phe" on of,alkali on the U
-the corres investigated the acti ore stable tovards
thors s group is much m deri-vat-i7,5-
The au ds and found that. thi he n-I)henol ,
the above comPOun ptiola of t after prolong"
tovards acia vitb the woe
alkal i than under the action of '"0" and giveS9 p batw&en the
w Ls off P The vinyl grou on th+
.hich spli th the alkalis n-coumaric acid- inishes its influence
boiling wi -Cr g-roup markedly dim
benzene, ring and the 3 4 non,-SoTiet,-bl,',,I,-
.,-bloc, and
Sovie-t
There wre 1() j-eferenCeS8 pu-blic-ations read OLE f0llOweg
ring, s to the English-laugaage A. TitleYq jo Chemo S0009
The refereucO .. SoC-.V'699 2346 (1947)1 10).
s9 J. Am- Chem 0,_ q-7 236, (19
R, 0. jone salway, J~ Chem; S
25719 1928; F. powerg
6
Card 4/i

S/079/62 032/009/006/OIT
1040/1242
ATIT110113 i Yagpipollijklyp L,M,.ar)d Maliohenkop J3.P-;.
TITLE, The derivatives of Ij,2-diphenyl-1,1,2,2-botrafliioro-
ethand, I. The o~mthasia of l,,q-dipheny1-1,1,2j$2-tetra- 1
fluoroothane-4,41-di-earboxylic acid
PERIODICAL:. Zhurnal obshchey Ithimii., v.32, no.9, 1962, 3035-303Q,
TEXT: Experimental methods for the syntheiiis of 1,2-diphnnyl-1,1,2, 1
2-tetraflitoroothano-4..41-dicarboxvlio acid (or its tetrnehloro ana-
log), some of its derivatives.. and some Intermediate prodnots are
dencribed. The -CFo-CF2- VOUP in these derivatives Imparts a high
resistance to hot alkal.Yne solutions. The'hydrol-yais of bis(n-tri-
chloromethyl)-benz one in the presence of ferric chlorido yi4~lded n-
trichloromethylbenzoylohloride which was the stsrting rqaterial for
mos of the synthesea reported. n-trIohloromethyl benzoic acid was
preparad by adding triethylamine to a solution of n-trichloron, ethyl-
benzoylehloride in. acetone in the presence of a small artiount of
water; the -mixture was allowed, to standovernight and mixed with a
Card 1/3

S/079
1048/1242
he derivstives of 1 2 -d ipheny 1.
T
10% IM11 Solutione The mothyl ester of this acid was prepRred by
adOtng. methanol nrd triethylomine to n solutiori of n-trichlorometh,11-
ban goylehlor id ein benzene,, The reaction of n-trichloroviethylben-
zoic acid dissolved in pyridine and Cu powder yielded 1,2-diphenyl-
.1. 2,2-tetrachloroothane-4 41-dicarboxylic acid, which, on boilin"
with thionyl chloride, yielded the dirviloroanhydrlde. 'A mixture of
this dieh-loroanhydride with antimony pontachloride. and anhydrou3 HP
was heated in an autoclave to 140-165uC yielding bhe analogous di-
fluoroanhydride -which on hydrolysis grive. 1..2-d lphenyl-l,, 1,2,2- tetra-
:'.fluoroo.thRno,-4,41-dicarbox-,viie Lcid, The ayntheal.- of tho following
compounds ara also described in detail: the dimethyl ester, the di-
midG, the diazidep and dilsoc-,vanate derivatives of both 1,2-dipho-
-4 -dicarboxylic acid and its tetra-
;-n,,tl-l,l,,2;2-tetraflucroethane ,41
chloro analog, as -well ar the synthesis of'4P41-bis(trichloromethyl)-
l,_0-diphrnyl-1,1- 2.,2-tetrachloroethanea
Card 2/3

GITIS S. S.;- GLAZ, A. I.1 YAGM-L'SKIT, L. M.
Reactions of aromatic ni.trO compounds..'Part 14: Effect Of
som eleetron'a'cceptor grOUPS on the reaction of re-e5teri-
fication. Zhur. Ob. khIm. 33 no.l.'IJL38-141 163
16:1)
1. Institut organicheakoy khimij AN UkrSSR,
(Esterification) (Nitro compounds)

Q, gg- ~B -

I !~~$
. e
...

YAGUPOLISFIY L M.; KLYUSFNIK G.I.; TROITSKAYA, V.I.
ontaining fluorine. part 1l.- Synthesis of cyanine dyes from
Cyanine dyes c -me thYlbenzimidazole. 2hur.ob.khim. 34 no.1:307-
fluorine derivatives of 2 (14IRA 17:3)
317 Ja 164.
1. Institut organjobsekoy khimij a UkrSSR.

YOMPOLISK11 L M., ORDA, V. V.
trifl(I.Orome hy-Lr4,vrcrpto) derivaLi-yes
1314,xifluoiomethoxy- and t
f Zhur. ob. Khim 34 no 6.1 ll~-,1994. Je 164.
bmzane -IT
(MURk 17.7)
o
1. lj:i_~titut organicheskoy khim*ii. 01 Uk-raill.4kay SSR.

YAGIJPOLI,SKIY, L.M.; pA.NTELEYMONOV, A.G.; ORDAY V.V.
YAgneBium, and lithium derivatives of trifluoromethyimethylsulfore
and their reactions. Zhur. ob. khim. 34 no.10:3456-3462 0 164.
(MIRA 17:11)
1. Institut organicheskoy khimii AN UkrSSR i Institut khimii polimerov
i monomerov AN UkrSSR.

- - ~~ - .--c n '!
-,%~ - -, -: - --' ;~- - -r.
idlono VP
YMONOV, A.G.* FIALKOV, YU.A.; Y.AO.UPOIIISKIYI
lo'ItOV, 'Yji.P.* PANTETZ
KULIK9 V.F.; YFX

4111M, N-t-1-4 'WI S-1 MeA
ORDA V.V. - IYAGUPOLISM, L.M. [lAhupolls,kyi, L.14.]; BYSTROV, V.F-;
I
TU~
"IANTS A.
S
and
Transmission of the induction effOCt Of SCF3 - SOC-;3
I substituents through the methylene grouP. bop. AN
SQ2CF3
URSR no-3:345-348 165. (14M 18:3)
institut organicheskoy kbi-ii. AN UkrSSR.-

--l-1. - ~ !~~
4. t4k~ ~~- lli~?Al-r-Pll~,~-w -
f-,jgq -- , - 'Alp
gill I

T M
Ir u-, )4
A-5 (j-3
ass
17
a. :na ,e:- a' [10 -1 ow, ariij Drai4,6 ~A r"; 3

nre usell se sonsiti-ers, Tle. rosidues of thecla ~
. , I r ~ -., 1. ---*~"-:---~t,,-r!,.,~,,-,!'-x',4-~ 77.f,l
. : -, ~ ~ : . . - a . I - . I I
k - - - I-

00
CT= t
No Ra SVI
Card 2t2
-M
F
mi,--!~.Mn MI-MOT N rRIN,

_= ~ q
lll~,Mw.~a.1793~;PIIIN;i BO~`.v ,
mum= - siammiammom - - - -- - - .- - - ~ - -- - - - - - - -

YAGUPOLISKrI, L.M.; MALICIIEUKO, B.F.
1,2-DipheTrjl-l-'--2-2-terlrafluoro--I.iians derivatives. Part 3z
Effect of 4,41-s-abstituents of A , -difluormtilene on the
addition-of fluorine. Zhur. ob. keim. 35 no.9:1561-1564 S 165.
(MT RA 18zlO)
1. Institut organicheskoy kbimii AN UkrSSR.

't, - 7- - , -,?, w~ AV2 q g~~ -!v=i m4c,;
6~- . ~r - , , lika, ~Vq*- -v
~~ 1~.! * ~.w, - , ~~Br , -VA i-