SCIENTIFIC ABSTRACT YURYEV, YU. K. - YURYEV, YU. K.

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• Document Creation Date: November 2, 2016
• Document Release Date: September 19, 2001
• Sequence Number: 15
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

Tetraacyl-oxy-Ailanes in Organic Synthesis, SOV/79-29-5,-12/75
21. Preparation of Acyl-6zy-t ijSploror'SiIanes F'rom Acids of Arowtic Wure,
solubility of the acids in silicon tetrachloride plays*'an
important part in the synthesis, Under the experimental conditions
silicon tetrachloride did not react idth other or acelono. The use
of the latter to attain a better solubility of the aoiis
accelerates, however, the formation of acyl-oxy-trichloro silanes.
The formation mechanism of acyl-oxy-trichloro silanes was
investigated on the example of the interaction of sillcon
tetrachloride with o-ohloro benzoio- and benzoic acid. By the
influence of excess silicon tetraoltIorlde upon the organic aoid
acyl-oxy-trichloro silane is formed without any intermediate products.
4hen studying the proyarties of the aoyl-oxy-trichioro silanes the
cleavage reaction under various conditions was invesiigated with
special thoroughness. It was found on benzoyl-,trichli,= silano that
its cleavage is especially cousiderable during distillation under
atmospheric pressure, in which connection benzoyl abloride, silicon
dioxide and silicon tetrachloride are formed (Ref 1'. On the basil
-o:e experimental data the following scheme of the thormal
decomposition of benzoyl trichloro silane can be established:
1~j Benzoyl-oxy-trichloro al-lana is disproportionatel in vacuum and
Cazd 2/3---- -on standing to give silioid'e and silicon tetrachloride. 2) The

Tatraacyl-oxy-silanes in Organic SYnthesis- SOV/79-29-5-112/75
21, Preparation of Acyl-Ozy-trichloro Silanes From Acids of Aromatic Natire
benzoic acid silioide is further olpaved to form benzoic
,anhydride and silicon dioxide. 5) The formed benzoic anhydride
yields under the influence of siliooatotrachlorido on ono h!,nd &-,d
of benzoyl-torichloro silane on the oiher hand benzoyl chlorido vd
silicon dioxide. Table 1~- the rate of the disproportionation of
aoyl-triehloro silanes; table 2 -.acyl-oxy-trichloro silvzos;
table 3 - disproportionation produoto of the aoyl-oxy-tziahloro
silanes; table 4 - tetra-acyl-oxy-sil~ges. There are 4 tables and
8 references, 3 of which are Soviet,
ASSOCIATICLIs Moskovskiy gosudarstvennyy universitat (Moscow State University)
SUHMEDz Nay 19, 1958
Card 3/3

50) SOV/79-29.-6-42/72
AUTHORS:. Korobitsyna, I- K., Severina, T. A., -Yurlyev,--Yu. K.
TITLE: Synthesis of the 4-Oxymethylene-2,2,5,5-tetraalkyl Furanidorles-3
6z 4-0 'Sime -tetraalkilfii-ranidonov-
(3 i.r.4 k tilen-2,2,5,5 3)
PERIODICAL: Zhurnal obshchey khimii, 1959t Vol 29-1 Nr 6,
Pp 1960 - 1964 (USSR)
ABSTRACT: In continuation of a previous paper (Ref 1) the authors describe
the synthesis of the f5-ketoaldahyda of the 4-formy1-2,2,5,5-
tetraalkyl furanidones-3. They found that the 212,5,5-tetra-
alkyl furanidones-3 enter the condensation with ethyl formate
according to the Claisen reaction. In carrying out the reaction
in absolute ether with finely ground sodium 4-ozymethylene-
2,2,5,5-tctraalkyl furanidones-3 are formed (yield 56-66~).
Card 1/3

V- ran I ky 1
synthesis of the 4-Oxymethylone-2,2,5,5-te' 30-1/79-29-6-42/72
Furanidones-3 HCOU (1)-R-RI-CH
0 3
(II)R=CH31R,.c 2H5
(III)R
HCOOC H
0 Na R' RI
Cl
Card 2/3
Theae furanidones are crystalline producto very unstable in air.
They must be stored in dark glasses if possible in unpurified
state. They take a cherry-red color with YeC1 and form groen
copper salts wi 'th copper acetate. The absorption spectra of
these copper salts in methanol. ahow in the ultraviolet range
the maxims, characteristic of the copper salts of the4dicarbonyl
compounds. The percent content of the enol, form was Mermined
according to K. Meyer (Ref 2) (Table ). The data in the table
show that the ketoaldehydes of the 2,2,',5-tetraa.lkyl fura.-
nidine series ~S-Well as of the alicyclic series (Refs 3,4) are
a mixture of the formyl and oxymethylene form which is in equi-

SyInthesis of the 4-Ox,ymothylone-2,2,5,5-tetraalkyI BOV/73-29-6-42/72
Furanidones-3
librium. In this case the latter considerably predominates.
The data on the table also show that with the increase of the
radicals in the Positicns 2 and 5 of the furanidine cycle the
enolization of the formyl group increases in position 4. In the
action of the benzoyl chloride on the pyridine solutions of
the compounds (I), (III), (IV) the corresponding O-benzoates
(VII),(V) and (IX) ware obtained. In the case of the action of
the sodium compounds of the same o.VLaethylene ketones the com-
pounds (VI), (VIII) and (x) were obtainod. (Ochome 2),, Thore are
I table and 4 references, 1 of which is Soviet~
ASSOCIATION: Moskovskiy gosudarstvennyy universitet (Lioscow State University)
SUBMITTED: blay 9, 1958
Card 3/3

50) SOV/79-214-6-43/72
AUTHORS: Yurlyev, Yu. K., Za-ytseva, To. L.
TITLE: The Chemistry of Selonophew (Kiiimiya selonofena). XVII. Con-
densation of the 5-Iltitroselenophene-2-aldf-,hyde With Compounds
Containing Active Mothylene Groups (XVII- KondensatsiYa 5-nitro-
selenofen-2-alldegida s soyedineniyami, soderzhashchimi aktiv-
nyyo metilonovyye gruppy)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, 11r 6,
pp 1965 - 1969 (USSR)
ABSTRACT: In continuation of the previous paper (Ref 1) 5-nitroselenophene-
2-aldehyde was condensated with compounds containing active
methylene groups which led to a series of 5-Aitroselenenal-2-
derivatives. Thus, in heating 5-nitroselenophene-2-aldehyde
with acetic anhydride and anhydrous sodium acetate P -(5-nitro-
selenienyl-2)-acrylic acid (421;v~) was obtained. The same acid
was synthesized by condensation of the same aldehyde with malonic
acid in the presence of pyridine with subsequent decarboxyla-
tion of the formed ra-carboxy- -(5-nitroselenienyl-2) -acrylic
acid (Schcjme~i). Thus, the oo0denoation of 5-nitroselenophene-
-Card 1/2 .--2-aldehyde with compounds containing activo methylano group3

The Chemistry of Sclanopliene AVII. Condennation of the SOV/79-21)-6-43/72
5-i'litrosole,no,r)hcne-2-alde~4ydc- Comoounda Contairin.,; Lctive Kiethylene
leads to the folloyling 5-nitroreleiianal-'Ql-tlerivative-s; P -(5-
nitroselenienyl-2) -acrylic acid ( in the cond ensat ion with ace' ic
anh~rdride or ma-1,--nic acid-scheme 1); u-al~41-~ -0-nitroseleni-
enyl-2)-acroleins (in the ::;oncensation with scetic, prop_i-~ziin
and butyric acid aldehide-sche.-Le
nltroethyl~-e ',it' th~- 1!~S.Lt ion witt, nitrociethanE-sc*h_-::--
.
~ci
tion wil~h rhodani,~-3~; 2 phenj
(ir, the condensation with hippuric ac~Jd-scheume 4). -nez-:~ alle
references, 2 of which are Soviet.
ASSOCIATION: Lloskovskiy gosudaarstvennyy universite, (Moscow State University)
SUBMITTED: May 9, 1958
Card 2/2

50) SOV/79-25-6-44/72
AUTHORS: Xurlyev, Yu, K., Sadovaya, N. K., Gallberahtaa, M. A.
- - - ------------------
TITLE: Chemistry of Selenophene (Khimiya selenofena). XVIII. Synthesis
of the Isomeric Trimethyl-Selenophene and of Tetramethyl Seleno-
phene (XVIII. Sintoz izomernykh trimatil--elenofenoy i tetrametil-
selenofena)
PERIODICAL: Zhurnal obsbehey khimii, 1959, Vol 29, Nr 6,
PP 1970 - 1973 (USSR)
ABSTRACTs The authors continued their investig,-.,~tion on the methyl home-
logues of selenophene (Ref 1). They made use of the possibility
of a subsequent formylation of the selonophene and the reduction
of the aldehyde group into the methyl group for the synthesis
of the trimethyl selonophene and of tetramethyl selenophene,
hitherto unknown. The synthesis of 2,36-trimethyl selenophene
was based on 2,3-dimethyl selenophene which, by the action of
dimethyl formamide, led to the 2,3-dimethyl selenophene-5--al-
deh7de. This aldehyde yielded the 2,3-dimethyl selenophene-5-
carboxylic acid in the caoe of oxidation with silver oxide. In
the reduction accordinC to tho goneral mothod bf Kizhner (Hof 3)
Card 1/3 'Whe 2,3,5-trimethyl selonophene was obtained.

ChGaistry of Selenophene. XVIII. Synthesis of -the SOV/?9-29-6-44/?2
--Isomeric -Trimethyl Belenophene and of Tetramethyl Selenophene
CH3 ]Q[__~PH 3- CH
C CH
an3 H31U- t~~Ro: 3
So
3,4-dimethyl 5elenophone served as initial product for the ayn-
thesis of 2,3,4-trimethyl 3elenophene. Its formylation yielded
3,4-dimethyl selanophene-2-aldehyde the oxidation of which led
,to the 3,4-:dinothyl-selehopbeno-2-carboxylic &aid. In the re-
duction of 3,4-dimethyl selenorihens-2-aldehyde 2,,'11,4-trimethyl
selenophene was obtained, which served-as initial product for
the synthesis of tetramethyl selenophene. In the foriVlation
of,2,3,4-trimethyl selenophene 2,3,4-triiaethyl selenophen-e-5-
aldehyde was obtained, which in the case.of oxidation formed
2,3,4-trimethyl sele""*phene-5-carboxylic acid, in the case of
reduction 33,4,54otramethyl selenophene (Scheme 2).. From the
tivo iaomeri~, trimethyl selenophene only 2,3,4-dimethyl seleno-
phene yielded the 5-chlor-o mercuri-2,3i4-trimethyl selenophene
by means of morcurizatiorl; tile 20,5-trizaethyl selenophene did
not enter this reaction.'Therc are 7 Soviet rafererces.
Card 4/3-

5 (3)
A "1090 j Korobitaynap 1. K.t 7,bukova, I. G. 7,07/751-29-7-20/183
If Ov YU.. K.
TITLE: Reactions of the 4-Bromo- wid wii-
dones-3 (Reaktsii 4-brom- i 4-oksi-2,266-tetraalkil-
furanidonov-3)
PERIODICAL: Zhurnal obshchey chfidi --19591 V61 29p ~Trj, p1? 2190-2196 (M5R)
ABSTRACT: The bromine in the 4-bromo-2,2t5,5-tetrenothyl furanidone-3 is
not substituted by the oxy group (in the hydrolysis with soda
solution), by iodine (in the action of KJ), by the thio-
cyanogen group (in heating with potassium thiocyanate),, by the
amino group (with ammoni 'a); only in the reaction with sodium
cyanide the corresponding nitrile is formed in good yield
(Refs 19 2). The aixthors used ouch halides for the synthesis of
the condensated systems which contain furaaidine- and thiazole
:rings. In the reaction -vith crystalline sodium sulphide at
135-1400 only the 4-bromo-2f2,5,5_tetraa1k,,r1 furaniaones-3
easily separated HBr, with the condensation ta!-Ana place under
-,the formation of thet-diketono with tvio furanidine rings
(Scheme 1). In the hydrogenxtion of (1) in Liao presence of
Card 1/2 _
nickel the 3--ketone (IV) resulted [the di-(2,20,5-tetramethyl

Reactions of the 4-Bromo- ane- 4-0:W-2~26,5-tetr-ailkYl Z-07/79-29-7-20/83
Puranidones-3
furanidone-3-Yl-4)], which with aniline led to d4anil M
_(Schewe 2). Already earlier (Ref 3) the authors used the
Paranidones (VI) for the-synthesio-of nitrogrenons heterocyclic
systeus with the furanidine ring. By this method the coupounds
(VII) and (IIIII) wero obtained froln 4-oYy-2p2p5t5-tetr'-;aethyl-
and 4-oxy-2,2,515-bispentaraothyletle furartidone-3 (Schemn 3)
whioh Lire weak aoida. The NrLmidonea (VI) react with a=onium
thiocyanate in moltina (I 00Y to fat-in furaaidino thiazoloo
(IX) , (X),' (XI) ('"'cheme 4~j A acheine of the -formation of those
compounds.is ouCgested. Thore aro 0 rofcrencoc,_2 of vehich are
Soviet,
ASSOCIATION: Mookovskiy gosudarstvennyy universitet State University)
ZUBT.1,1TTM: July 2, 1958
Card 2/2

5 (3)-
AUTHORS: x6robi tsyna, 1. X., Zhukova, I.- G. SOY/79-29-7-21/83
--,Yurlyev,

TITLE: -3 -Atsetil-2,2,5,5-
4-Acetyl-2,2,5,5-tetraalkyl Ydranidones
-tetra-alk ilturanidonY-3)
PERIODICALs %hurnal ob-shchey khimiit 1959t Vol 29, Ur 7, pp 2196-2201 kUSSR)
ABSTRACT: Xarlier kRef~i) the'authors showed that 4-aooty14j2p5s5-
-tetramethyl furanidone-3 forms in the thermal iriomerization
of the enol acetate of 2,2,5#5-tetramethyl furanidone-3. in
the present paper they tried to apply this method also to the
synthesis of the nigher homologs of 4-acetyl-2,2,5,5-tetra-
alkyl furanidones-5. It was found that in passing the enol
acetate of 2,5-dimethyl-2,5-diethyl furanidone-5 through a quartz
tube filled with glass wool and which had been heated to 5000
this enol acetate isomerizes into 4- acetyl-2,5-dimethyl-2,5-
-diethyl furanidone-5 k15,6%yield)kScneme 1). rurther in-
vestigations showed that with increasing radicals in the
positions 2 and 5 the yields of the products of thermal iso-
merization in the enol acetates of ZP2,5,5-tetraaikyl �uranidones-3
Card 1/2 kof the corresponding 4-acetyl-2,2,5,5-tetraa1kyi furanidones-5)

A-Acetyl-Z,2155-tetraalkyl Yuranidonaa-3
are abruptly reduoed. This method, however, ie otill the only
one possible for the sYnthesis of 4-acetyl-2j2,5,5-tatramethyl
furanidone-3 and of 4-acetYl-2,5-ctimethyl-2.5-diethyl furanidone-I
since other experiments failed. The two oxy-ketoneB kIII) and
tIV)-may occur-as-tcutomeric forms of 4-acetr1-2,2p5,5-tetra-
methyl turanidone-5tlI).-'4-ac6tyl~-212,5,-5-tetramethyl-furanidone-5
iq enoiized in a nigh degree in the direction of the exooyclic
carbonyl aroup; it forms U- and U- derivatives according to the
conditions of acylation. 'The ~-diketones of the 2,2,5,5 tetra-
alkyl.furanidine series require much more rigid conditions in
.the reactions leading to the condensated heterocyclic systems
than the aliphatic or aromatic P-diketones. There are 8 refer-
ences, 2 of which are Soviet.
ASSOCIATION: Moskovskiy gosudarstvennyy universitet (Moscow State University)
SUBOTTED: JulY 2, 1958
Card 2/2

-42/83
NOV
tion of 242ino-
AUTRORS Demill"r s of the KeaC
the I)roduct produkta
troyenii
tructur-e-Of~_
Yi ItI, Lx_ojt~,,~des _okisY!%2:V)
-On
------T-jTLE: thyl-thiazole azols-,
-4 ~,me til i
-4
tviya 2-a2ino mia 9-2'502
vzaimodeYs Vbl 29, lqr 7, pp 229
zhurnal obshchey k-nimii' 1959,
F,Rl:t)'DICA,Ls ossit) coworkers
1) arlyev and
-o:CY-
ection with a previous paper by Yl n
In conn yntheaized the hit-nertO unknow
order to
PBsTRkCT 1 the authors s by two different methodis in I deriva-
ARef the OXYalky
lkyl)-aminothiazOlOs , the struOturO Of tion Of the
a in simu),taneousl'. ith
4-methYlthiazOle obtained by real
ascerta thiazole derivatives ion
f 2-aminO- ntlY the react
tives 0 des. Appare' formed in
lattOr with (X-07-1 it atoms are not )iamines in the manner
,j.kylated ring-nitrogen gith alkan, .4-methyl-
-methylthiazole re,action Of 2-chloro-
-of --2-chlorO--4 -_ -R-f- 5).--~Y ----ne--2_k~_oxyethyl
described, here k e nd 2-propancll*aolaio-4-methYl+~"~ELole
thiazOle with ethanolamine a 2-kPOXY-Propyl)
4-methylthiazole and
amino-
Card 1/2

000
Un the Structure of the Products of the Reaction uov/*(9-29-7-42/85
of 2-Amino-4-methylthiazole ftith a-Uxides
respectively were obtained. A comparison of the constants of
these compounds and their derivatives with the constants of
the compounds synthesized by the authors by reaction of 2-amino-
4-methylthiazole with the corresponding oc-oxides kRef 1) proved
to be identical. This waa also confirmed by the identity of
the infrared absorption spectra of the ?-(P-oxyethyl) amino-
thiazoles obtained by different methods and tho ultraviolet
absorption spectra of their hydrochlorides (reaction scheme)
Thus cc-oxides react differently with 2-amino-4--methylthiazole
than with 2-aminopyridine and yield 2-(O-oxyalkyl) amino-
thiazoles,'there'ay retaining the thiazole structure. There are
I figure,_1 table,- and 9 references, 4 of which are Soviet.
ASSOCIATION: Moskovakiy gosudarstvennyy universitet tMoscow Utate uniiersity)
SUBMITTED: -June 18p 1958
Uard 212

50) SOY/79-29-8-3o/81
AUTHORS: YurfyeYt.Yu. K., Balyakova, Z. V., Kostetskiy, F. V.,

TITLE: Tetraa,-yloxy-silanes-in Organic Synthesis. XXIII. Acylation
of Amines, Arylhydrazines-and Acid Hydrazides With Tetraacyl-
oxy-silanes
PERIODICAL; Zhurnal obshchey kbimii, 1959, Vol 29, Nr'fS,
pp 2594 - 2597, (USSR)
ABSTRACT: Previously (Ref 1) the authors described the acylation of
. diethyl-amine with tetraacyloxy-silanee as a convenient syn-
thesis of the 11-N-diethyl.amides of the seiturated monobasia
organic acids (yields 6o-go%)
+ 4 NO 'R# --)o 4 RCONR IR" + S'(OH)4' It suggested
(RCOO)4S'
1
itself to synthesize also other N,N -dia Ikyl- and N-alkylamides
of the acids in the same way, and to uso this method for the
synthouis of tho J(-ijr,~dlethylamides of,';he aromatic acids,
especially benzoic acid# o- and a-toluio acid3 (Refs
The acylation of dibutylamine was carried out with tho silicio
Card.1/3 anhydrides of acetic, propionic, butyric and caproic acids

sov/79--29-8-3o/81
Tetraacyloxyl-silanes in Organic-Synthesis.,XXIII. Acylation
of Amines, Ary1hydrazines and Acid Hydrazides With Tetraacyloxy-,~ilancs
in which connection the NpF-dibitityl-acyllamides of these acids
were obtained in yields of 65_81%,. Acylation of diethyl
amine with the silicic anhydrides of benzoic acid, o- and
n-toluic acids.yielded the N,N-diethyl-benzamide (63%), N,11-
diethyl-o-toluamide --(24%),-and N,11-diethyl-p-toluamide
The deorease.inthe acylation-ca;pability of the tetraacyloxy-
-silane-with increasing ao iditywas,already previously observed
by the authors (Ref 4)-~Acdording to 0-Friedel and A. Laden--
burg (Ref'5), acetamide and If-ethyl acetamide were obtained in
yields of only 12% and , accordingly, 5-i5ri; on letting through
ammonia and ethyl amine into the benzene solution of the si-
licon-acetic anhydride. The-acylation of ethyl amine on
0
heating with tetraacyloxy-silanes in the autoclave at 100
gave the N-ethyl amides of the acetic, propionio, butyric, va-
.1erianic, isovalerianic and caproic acid in yields of 33-82;~'-
The acylation of phenyl hydrazine with the silicic anhydrides
of acetic and propionic acid yielded the phenyl hydi,azides
of these acids (67 and 61%)t
4 C6H5NTHNH2+ (RCOO Y' 4 C 6H NLHNFICOR+ S'(()H)4 The re-
Card 2/3

BOV/79-29-8-30/131
Tetraacyloxy-silanes in Organic Synthesis. XXIIIw .
).cylation of Amines, Ary1hydrazines and Acid 1~ydrazj dp~s -4th Te'traaac,710XY
silanes
es
sultant substituted amides and hydrazid
tainedIby the above-nentioned a0ylation, their yields and
constants, are presented in the table. There are 1 table
and 29 rofere.noesp.7 of whichare Soviet-
AsSOCILTIONt Lloskovskiy gosadarstve .nnyy universitet NOB00W State Uni-
versity)
SUBMITTEDi July 2#
Card 3/3

-29-8-31 /61

-5-0- sova3

Yurl
the
.
in
-
2;4c6tO-se
1y_
elenopheng
elenopbene-X
ldehydes in the
Chemistry- of 5
T ITLE and -Keto-a
Synthesis Of a-
Series
VO1 29' "r 8'
,nsl obshcheY khimii, 1959,
Zho
pERIODICkL: (USSR)
2597 - 26o
rs
th
o
u
pp
3 (Refs e FL
r
o their previous pape
-acyl-selenophenes for the
-
ddition t
3S T RA CT a
the a
In present paper, le
bonyl compounds in the se
d in the
f
-aicar
use
a by oxidation O
synthesis of the a- and. 0.ay
they obtaine
ienJl-2-
'
,
selen-
s dioxide the
nophene series. In th
ith selenium
of which
'ht-yelloW color
2 -ac cto-a elenophene w
de the brig nyl
f "'o 0'fb'
h
ld
e
y
to-a
yoxalT a ke f the double bonds O
gl r liolet ab-
njugation I
The ult a
c0
s.
i sdue to a f the selenophene nucleu has
lyoxal (Fig
2-
d 0
g
con-
groups an
tium of the seienienyl-
compound is eas.-LlY
ec
s
h
- ------ e
p
T
rption
so-- -- -
im& t),-2T5--and-3i0-1'1P-1*
-a --
d forms
uc
an
two-ma
action
O.Phonylene diamDl% -(~Gheme I By thQ
d with
dense
ienyl-21)-quinoxali e
2-(selen
Card 1/2 the
J:

ChoLAstry of Selenophene. XIX. 2-Aceto-aelenophene in SOY/79 -29.6-31/81
th e Synthesi a of a- and -Kato -aldohydea in the Selenophone serie:~
of alkali lyes on its monosemioarbazone and monothiosemi-
carbazone, water is split off and, accordingly, the 3-OxY-
and the 2-mercapto-5-(selenienyl-2l)-triazine-1.2,4
(Scheme 2). On condensation of 2-aceto-selenophene with the
ethyl ester of formic acid under the influence of sodium,
the sodium alcoholate of oxymethylene-(selenieziyl-2)-ketone
is obtained which is of dark-violet* color in the thiophene
series. Its absorption spectrum is characterized in fig-are 2
by curve 10 the one of its intramolecular complex compound
with Cu++ by curve 11. There are 2 figures and 4 Soviet re-
ferences.
ASSOCIALTIONi Moskovskiy gosudarstvannyy universitet (Moscow State Uni-
versity)
5UBIMITTED; july 2, 1958
Card 2/2

TITLE: Investigation in the Series of Furan.
1. Synthesis of the H-(p-Oxyalkyl)-furfuryl Amine
Zhurnal obshchey khimii, 1959, Vol 29, Nr 9, pp 2951-2954
(USSR)
ABSTRAM 4~~F-plr'osent -pa;Iier deals with the synthe~sia -of- the mono-H-
i es f ryl amine and the
alkyl) furl' -1-4m n -from_2~fur a
oxy
simplest a-oxides (oxides of othylene
ing to a method already earlier developed by the authors-
(Refs 6,7) and taking account of the papers quoted in ref-
erences 1-5, among them the paper of A. A. Ponomarev et al.
(Ref 5). According to the previous method, ethylene oxide was
al-loved to flow into the amine. The corresponding N-(P-Oxy-
alkyl)-furfuryl amines resulted in an 86%-yield. The yields
were 83,5-92,5% at higher molar percentages of the a-oxides
in the reaction with furfuryl amine. The properties of
di-N-(P-oxyethyl)-furfuryl amine as synthesized by the authors
were completely different from those of the preparation des-
Card 1/2 cribed.by German authors (Ref 5): it in a colorless oil; its

SOV/79-29-9-30/76
on in the Series of Futano
Investigati a of the N-(P-o%yalkyl )_furfuryl A-m Ile
-1. Synthesi 127-1280; its refractive index is higher.
structure:
ASSOCIATION:
SU BMITTED:~
picrate melts at rption spectrum confirms its
Ito infrared absc ,king frequenoiOs which are characteristic
characterizing the
instead of the Is ;ha~re is a bros-d band ad in
-of ~the N~jj-bond- I-- -- dr- -.jVj,oride waa obtain-,
group O-H. No ICrYstalline hy 0
ssage of hydrogen chloride through tha chloroform hlo-
the pa . In the reaction with thionyl 0
solution- of the preparation -furfuryl
oride of di-N-(p-ethYl chloride)
he hydrochl -thiamorpholine
ride t ~d N-(2-furfur7l)
amine resulted which yielde 2 Schemes). The given ryl
under the action of sodium sulphide ( L-N-Woxyethyl)-furfu
data which confirm the structure of al mistook this;
.- Drefahl and K. K6nig (Ref 5)
amine show that G th a-oxides di-(2-furfuryl amine, 3~
Compound for anot.her one-Wi sin high yields(Scheme
N-(p-oxyalkyl)-difurfuryl amine Soviet.
forms are 9 referenceat 4 of which are sity
There gosudarstvennyy universitet (Moscow State U111"ar
Hookovskiy
July 14, 1958
card 2/2

50Y
AUTHORS: Yur I yev, Yu. K. ,Zefirov, 11, S. SOT/79-29-9-31/76
TITLE: Investigation in the Series of Furans
II. Reaction oil Compounds of the Furan Series With tho
Diethyl Eater of Azodicarboxylic Acid
PERIODICAL: Zhurnal obshchey khimi-L, 1959, Vol 29, Nr 9, pp 2954-2960
(USSR)
ABSTRACT; On the basis of a number of papers quoted in references
1-30 the authors investigated the reactions of the diethyl
ester of azodicarboxylic acid with furan, 2-methyl furan
(silvane), and furyl alcohol. After the experiments were
finished, P. Baranger and J. Levisalles (Ref 5) published
a paper describing the failed experiment in which the attempt
had been made to cause furan, 2-methyl furan, and 2,5-dimethyl
furan to react with the above ester. The mentioned research
workers did not succeed in inolating the formed adducts and
in carrying out an alkali and acid hydrolysis of the reaction
products. In the experiment described the reaction of furan
and 2-methyl furan with the above ester was found to proceed
like a diene synthesis in which compound (I) and, accord-
Card 1/3 ingly, (II) result qualitatively. A large quantity of ether

has to be used for these reactions as without a solvent they
would proceed vigorously and cause resinification. Adducts
(1) and (1r) are non-crystalline, solid, glassy products,
softening in powder form at 50-600t in contrast to the adduct
of the same ester with the diacetate of furfurole (Ref 9).
The adducts (1) and (11) add easily to bromine, yielding -
lasay dibromides (111). The reaction with phenyl azide
Refs 31-32) leads to a crystalline triazoline 4erivative (IV),
~
but only in the adduot (1). Hydtogen is added to the adducts
(I) and (11) which yield dark, glassy producto (V). In
vacuum distillation a pyrolysis takes place (compound (71)).
When heated with phoSDhorus pentoxide (1) and (I!) resinifyt
developing CO,, ethylene and forming a small amount of di-
ethyl esterof bydrazo dicarboxylic acid, which in turn
decomposes under the formation of ethylene, CO., and nitrogen.
The chemical properties of the adducts (I) and (H) and
especially the formation of the crystalline addition p-roduct
Card 2/3 of phenyl azide to adduct (I) indicate that the reaction of

5M
AUTHOR.%: Z. V. SOV/79-29-9-32/76
TITLE: Tetraacyloxysilanes in Organic Synthesis.
XXIV. Reaction of Totrameylox",ilanes With Organomagnesium-
and Organocadmium Compounds
PERIODICAL: Zhurnal obshchey khimii, 1959P Vol 29, Nr 9, pp 2960-2964
(USSR)
ABSTRACT: Two kinds of reaction are characteristic of acyloxyoilanes;
(1) Reactions taking place under the decomposition of the
C-0-bond; (2) reactions taking place under the decota-Dosition
of the Si-O-bond. All acylation reactions with tetraacylaxy-
silanes belong to the first kind: acylation of the benzene
cycle, thiophene, selenop#ene, pyrrole (Refs 1-4), of malonic
ester, acetoacetic ester (Ref 5), and amines (Refs 6,7)
(Scheme 1). in continuation of the collected investigation
data of the papers quoted in references 1-11 the authors
of the present paper inveatigated the reaction of totraacyl-
oxysilanes with organomagnenium- and organocadmium compounds;
theoretically, two directions ot reaction were possible due
to the decomposition of the C-0- or Si-O-bonds, i.e. accord-
Card 1/2 ing to schemes (IV) and (V). Taking account of the papers

Tetraacyloxysilanes in Organic Synthesis. SOTI/79-29-9-32/76
XXIV. Reaction of Tetraacyloxysilanes With Organomagnesium-
and Organocadmium Compounds
quoted in references 12-17, the reaction of silico-acetic
anhydride with alkyl magnesium halides was investigated; in
all cases tertiary alcohols were obtained in yields of
58-68,5%, tetraalkyl silanes (51-72%), and fractions with
a high boiling point (apparently siloxanes). All these data
as well as the absence.of silicie acid show that the reac-
tion of tetraacyloxysilanes with organomagnesium compounds
takes place under the decomposition of the Si-O-bond accord-
ing.to scheme (V). The stability-of this bond decreases with
increasin6 acidity of theorganic acid in the sil.ico-acetic
anhydride which result.3 in a higher, reactivity of totraacyl-
oxysilane towards the organomagnesium compound. Ketones
(20-46%) and silicia acid resulted in the reaction of silico-
acetic anhydride apparently under the decomposition of the
C-0-bond according to scheme (IV). There are 28 references,
13 of which are Soviet.
ASSOCIATIONL Moskovskiy gosudarstvennyy universitet (moscow State University)
SUBMITTED: July 4, 1958
.--Card 2/2

AUTHORS: Shcherbakov, A.L., Yurlyev, YL'.K. SOV/130-3?-2-25/56
TITLE: The Effect of Preliminary Processing of Plant Raw Material by
Organic Solvents on the Formation Dynamics.and Yield of Fur-
furole (Vliyaniye predvaritellnoy obrabotki rastitellnogo
syr1ya organicheskimi rastvoritelyami na. dinamiku obrazovaniya
'i vykhod furfurola)
PERIODICAL: Zhurnal prikladn IN Ji 19591 Vol XXXIII Nr 2,
1m1
pp 374-382 (USM 7
ABSTRACT; The preliminary processing of pentosan-containing raw materi-
als by various solvents increases the output of furfurole by
preventing resinification during hydrolysis. In the experi-
ments hydrolysis was carried out by a 124 solution of hydro-
chloric acid. Table 1 shows that the pentosans in corn cobs,
barley husks4 oats chaff, etc are most easily hydrolyzed. The
preliminary treatment'of the raw materials by alcohol, ether,.
chlorof
ormt benzene, gasoline, CCI 41 etc has a considerable
,
effect on the furfurole output as well as on the dynamics of
its formation. If the raw =.torial is preliminarily treated
Card 1/2 by vaseline oil, diesel fuel,' etc and then hydrolyzed by a

sov/60-32-2-25/56
Pre:.Liminary Processing of Plant Raw ~Jaterial by Organic solvents
The Effect O.L of -FurfurolO
on the Form,_~.tion :Dynamics and Yield ~put of furfurol e in-
id, the Oul yield without the
_01u,*jon of sulfuric ac
on with the
creases bY 43,4' in comparis
solvents * and 11 references, of which are Scvi St
There are 2 tables
3. Amerjc~,n, 1 En."lish, and 1 Ge,,a,,*
siul3MITTED 1957
card 2/2

50) SOVI'20-126-4-32/62
AUTHORS: -Yurlyev, Yu. I.,' J;ovitskiy, K. Yu., ""hingareva, V. N.
TITLE: Investigations Into the Furan Series-(Iosledovaniye ryadu
furana). The Synthesis of Symmetric 2,5-bis;(dialkylamino-
methyl)-furan (Sintez simmetrichnykh 2,5-bi -(dialkilamino-
metil)-furanov)
PERIODICAL; Doklady Akademii nauk SS3111, 1959* Vol 126, 'Tr 4, pp 606-808
(USSIO
ABSTRACT: The furans mentioned in the subtitle are hardly described
in publications. 2,5-bis-(4imethyl-aminomethyl) furan was
obtained with a very small yield (Ref 1). Diamines of such-
structure, as well.as their dihaloid alkylates are of inter-
est as potential, ganglion-blocking# and ouraro-like compounda,
with regard to their physiological activity. The authors used
2t5-bis-chloromethyl furan for synthesizing symmetric diamines
of the mentioned structure. Its peoiprocal action with secondary
amines showed satisfactory results in the production of the
corresponding diamines (see scheme). The reaction develops
easily with th-6--reciprocal-action of etheric solutions of
bis-chloromethyl furan with secondAry-amine-in th -e presence
Card 1/2 of caustic alkali. From among the secondary amines-dimethyl- ----

SOV/2o-126-4-32/'62
Investigations Into the-Furan Series. The Syn-hesis of Sy=etric 2,5-bis-
(dialkylaminomethyl"-furan
amine and diethylaminev piperidinet and morpholine were added
to the reaction. Thus 2 5-bia-(dimethyl-aminomethyl)-2,5-
bia-(diethylaminomethyli, 2,5-bia-(piperidine-mcthyl), and
295-bis-(IT-morpholine-met'hyl)-furan were prodvi-,ed. The constants
corresponded to those.produced by means of another method
(Rof 1). Tho roc;procal action hQra doncribed of 2)5-bia-
chloromethylfuran with secondary aminun, up to now hatj boon
the only comfortable way producing the corresponding symmetric
amines of the furan series. There are 3 references, I of
which is Soviet.
ASSOCIATION: Moskovskiy gosudarstvennyy universitet im. !,',. V. LomonocoVa
(1doscow State University imeni H. V. Lomonosov)
PRESERTED.- March 5, 1959, by A. N. Nesmeyanov, Academician
SUBMITTED: February 28) 1959
Card 2/2

5(2) SOV/20-126-1-32/58
AUTHORS: Yurlvev,, Yu. K.9 Makarov, N-,- V.
TITL9. Transformation of Furanidine and Tetrahydropyrane Into the
Reupoctive Silicon-containing llotarooyoloa, Trannformation
of the Latter Into Sulfur-containing Heterocycles
PERIODICAL: Doklady Akademii nauk SSSRg 19599 Vol 126, Nr 1. pp 121-123
(USSR)
ABSTRACT: In the present paper the catalytic method of interchangeable
transformations of heterocycles discovered'by one of the
authors (Ref 2) was applied. The furanidine was caused to
pass over aluminum oxide in the monosilane flow at 3750, thus
obtaining simultaneously tetramethylone silane (0) and di-
tetramethylene silane (1.5%). The latter is the transformation
product of furenidine under the actioa of the tetramethylene
silane formed. Subsequently, a mixture of furanidine and
tetramethylene silans was passed over aluminum oxide, and
ditetramathylene silane (4.5%) was formed, A similar trans-
form'ation of furanidine under the action of ethyl silane proved
to be impossible aino.e the latter completely decomposes at
Card 1/3

SOV/20-12a-1-32/58
Tranaformation of Fur4nidino and Totralkvdropyrana Into the Respective
tho Latter Into
Sulfur-oontaining HeUroc cles
0
the contact with aluminum oxide at 350 Tetramethylene silane
was also obtained by a commo'n catalytic dehydrogenation of
butanediol-1-4 and monodilane under the same conditions. In
the case of action of'hydrogensulfide on tetrame thylene
silane or tatranethylene dichloro siland the cyclically
bound silicon atom is replaced by sulfur, thus forming
thiophane (14~ and 4%. respectively). Tetrahydropyrane trans-
forms to pentamethylene silane (9.5%) under the action of
1 0
monosilane at the contact with aluminum oxide-at-57-5 . Under
the samo conditions,pentamethylena silane.is-transformed
to tetrahydrothiopyrane.underthe action of hydrogen sulfide.
There are 7 references, 5 of-,ohich-are-Somie.t.

00
:'57 3/00- 6726f

LUTHORS: Stradint;. Ya.p Gillerp S. Academician SOT/20-129-4-2s/68
AS LatvSSR# Yur'Xej, Yu.

TITLE: Polarogra~hio Reduction.of 2-Mitrofuran Derivatives and
2-11itroselen2ghenADerivatives
.PERIODICAL: Doklady Akademii nauk SSSR, 1959, Vol 129, 9r 4, pp 816 - 819
(USSR)
ABSTRACT: The authors ascertained the influence exercised by the substitu-
onto in the 5th position of the furan- and selenophene oyole on
the polarographia reduction process of the nitro groups in the
second position. Thus, they completed the data of publications
by new examples. The derivatives mentioned in the title may now
be compared to the rLitro derivatives of the aromatic series.
Table I gives the derivatives I-UV investigated in the present
paper under vigorous conditions, I t was found that the aschanism
of polerographic reduction of the mentioned derivatives is the
same as that of nitrobenzene- (Ref 7) and, of 2-nitrotblephens
(Ref 11) derivatives, Also*tho semiwave potentials E of the
4
elated.
nitro derivatives of the mentioned series are alosell
The comparison of these series leads to the conclusion that the
card 1/3 nitro group of 2-nitrofuran derivatives is the most easily to be

6726f
Polarographic Reduction of 2-Nitrofuran Derivatives and soir/2o_129-4-2s/6a
2-Nitroselenophene Derivatives
reduced. This is more difficult in the ease of 2-nitrotblophene-
an& 2 nitroselanophene (which requires by 20-30 my more) and
still more difficult for nitrobenzene derivatives (by 40 nvm=o).
From the investigation of this series of derivatives the influ-
once exercisad by the subatituents on the polarographio reduc-
tion of the nitro group may be quantitatively estimated on the
basis of the E1/2 displacement of the substituted compound com-
pared to the non-substltuted one. In the series of nitrobenzene
and uitrothiophene this displacement may be expressed by the
Hammet equation, It may be concluded from the data given by the
authors that this holds also for the derivatives mentioned in
the title if the same values of 6 4re assumed for the substitu-
ents in the heterocycles as a ply for the aromatic seriesp and
if the numerical values of 4SPI /2 and f are compared for an equal
pH value in-& iteakly acid medium, The behavior of the 2#5-sub-
atituted derivatives of-th-e 5-membered heterocycles corresponds
to the behavior of the p-substitates of the aromatic seriee.
The behavior of the former however strongly differs from that
Card 2/3 of the m-substituteso This agrees on the whole with the rules of

67264
polarographlo Reduction of 2-Mitrofuran Derivatives and SOV120-129im-448168
2-Nitrosolenophons Derivatives
r4 orientation found in the study of the reactivity of the substi-
tuted furans. However, further polarographic measurements are
necessary in this case. The influence exercised by the substi-
tuents over an additional.group .70Z.=03- in the side chain to
in general not high. The reduction of 5-zLitro furfurol proceeds
in e. characteristic manner (Soheae). There are I table and
16 references, 9 of which are Soviet.
ASBOCIXJ-~~ON; Institut organicheakogo sinteza Akademil, naulc LatvflsR (institute
of Pyganio Synthesis of the Aoadezz or sciences of the fa-tvi
SSR)i Moskovskiy gosudar.Avennyy universitat Ime M. V. Loionosova
cow State University !;sni M. V. Lomonosov)
SUBMITTED: July 219 1959
Card 3/3

yuafyLv Tu~r.; 13WAMYA#--Z-V ;-vOIKOT,-V.P,,,-OSADCHAYA R.A.;
SHAYDEROVA, L.P. ----- --
Totraae7loxysilanea in organic synthesis.- Fart 28; Ac7lation of
benzene by silicon-p-chloropropionle atd-IC-Chlorrobutyric anhydrides.
Part 29: Preparation of organic acid anhydrides from their silicon
anhydrides. Vest.Hosk.un.Ser. 2: Xhim. 15 no.1:61-67 t6o.
(MIRA 13:7)
1. Kafedra argantohosko7 khimii Mookovskogo universiteta.
(Silicon organic compounds),
(Anhydrides)
(Acylation)

Ymtyzv. TSI.K.; Mmol 0,14* Yosk un. Ser. 2*-
-alkYltetrawrop7rea, (KIRA 13.9)
37uthesis Of 2 160.
15 nook:74-70 A-Ag
go- aratteta,
raf e4ra orgeadelleako7 klil6it moskovsko un v
(pyran)

Yr
PA
81974
S/074/6o/o29/07/01/004
00 13020/R066
AUTHORS: Yurlyev, Yu. K., I'LeLy-a-kova1z. V_
TITLE: AcyloxfgilanesA
PERIODICAL: Uspekbi khimii, 1960, Vol. 29, No. 7, ppo 809-832
TEXT: Acyloxysilanes covered in this review are monomeric organosilicon
~compounds with at,least one acyloxy group bound to the silicon atom.
Well-known types of acyloxysilanes are tetraacyloxysilanes,with the
general formula Si(OCOR)4 alkylacyloxysilanes Rx$-4(OCORI)4-xy
alkoxyacyloxyailaneii (RO)xSi(0COR')4-x, alkylalkoxyacyloxysilanes
RX(R'O)ySi(OCOR")4-x-.Vp and acyloxytriohlorosilanes C'3s'OCOR' Compounds
like aminoacyloxysilanes (NJ'2)xS'(OCOR)4-x and (alkylthio)-acyloxysilanes
(RS)XS'(OCOR)4_x are unknown.,F~om the day when the first acyloxysilane
tetraacetoxysilane -,was synthetized (1868.) until 1947, only 15 papers
Card 1/2

71"W-47 ---------------------------------
_t ------------
81974
Acyloxysilanes S/07 60/023/07/01/CO4
B020YB066
dealingwith these compounds had been published, while during the last
to 12 years more than 100 thearetical and practical papers have
appeared on this subject. This io due to their growing practical
importance. A review of methods used for the preparation of tetra-
acyloxysilanealand acyloxytrichlorosilanes, alkyl- and arylacyloxy-
silanes, alkylalkoxyacyloxy- and alkoxyacylox~silanes, as well as of
the-reactions of these compounds is given. Yu. He Vollnov, G. B.
Yelyakov, Vo P. Volkov, Be H. Dolgov, K. P.- Kharitonov,-M. G. Voronkovp
I. G. Khaskin, V. P. Davydova, K. D. Petrov, Me I. Itkinav- Ye. S.
Lagucheval A. N. Resmeyanov, E..G. Perevalova, A. N. Vysokooovp Ko Ao
Andrianov, V. G. Dubrovinal and-T. N. Ganina are mentioned. There are
151 references: 74 Soviet, 28 US, 18 British, '18 German, 7 French, 2
'Italian, 1 Austrian, I Swedish, 1 Indian, and 1 Japanese.
ASSOCIATION; Xhimicheskiy fakulltet MGU im. Me V. Lomonosova
(Chemical Department of Moscow State University imeni
M. V. Lomonoso
Card 2/2

5.3610 77358
SOV/79-30-1-19/78
AUTHORS: Yurlyev, Yu. K., Zaytseva, Ye. L.
TITLE: Chemistry of Selenophene. XXIV, Condensation of 5-
Nitroselenophene-2-aldehyde.and,,/3-(5-Nitroselenienyl-
2)-acrolein.Wlth lijdrazine Deri tves
PERIODICAL: Zhurnal obshchey khimii, 1960, Vol 30, Nr 1, pp 98-101
(USSR)
ABSTRACT: Condensation of 5-nitroselenophene-2-aldehyde and
(5-nitroselenienyl-2)-acrblein with hydrazides of
cyanacetic, furancarboxylic, and isonicotinic acids
yields the following compounds, not described In litera-
ture: 1-(5-nitroselenenal-2y2- cyanoac ety I hydra zone,
yield 93%, mp 241-2420; l-(5-nitroselenenal-2)-2-(2-
furoyl)hydrazone ield -_ 100%' mp 266-26,iro (decomp,
1- d' A
from alcohol); 5-nitroselenienyl-2)-allyli e
-1hy - -2210
-2-cyanoacetj dra one, yield __,100%, mp 219
(decompi f4olit alcohol); 1-[[~ -(5-n1troselenienyl-2)_
allylidenej .-2-(2-Vuvoy1)hyd axonu,, yield 96%, mp 225-
Card 1/4 2270 (decomp, from alcohol); 1-6-nitro8olenonal-2)-2-

Chemistry of Selenophene. XXIV 77358
SOV/79-30-1-19/78
isonic-otinoy1hydrazone, yield 91%1 mp 243-2440 (decomp,
from alcohol - 5-nitroselenienyl-2)all~lidenLj
-2-isonicotijrioy3 ~r~z 94%, mp 2114-245
lj one, yield
(decomp, from alcohol). Reaction of 5-nitroselenophene-
2-aldehyde with semioxamazide and, 5-( hydroxyethyl)-
semioxamazide yields the following seAcoxa-mazones, not
-nitroselenenai-2)semioxama-.
described in literature. 1-0
zone,_yield 9Z;~ 100%, mp 252-2530 (decomp, from alcohol),
and 1 (5-nitroselenenal-2)-54, o-hydroxyethyl)-semi-
oxamazone, yield 90%, mp 251-2PT (decomp, from qlcohol).
+19,NNHCOR
OIN \so /-(CII---GII)*-CH=NNHCOFt
0 \so/
(fit)
(X "t-0 S 1); (11 it -'O~pv i. U-CIIAGN- C41'30- CekMl (111 M-0; W-11, CH&CIQ011).
Card.2/4

Chemistry of Selenophene. XXIV 77358
SOV/79-30-1-19/78
Condensation of 5'-nitroselenophene-2-aldehyde and 13 -
(5-nitroselenieqfl-2)-acrolein with 1-aminohydantoin
and 1-amino-2-thiohydantoin yields the following com-
pounds not dese,ibed in literature: 1-(5-nitroselen-
-21-mino 'L' .5%,mp 263
enal. hydantoin, yield 81 -2640 (deco p,
0
from alcohol); 1-fj~ -~S5-nitroselenienyl-2)allylideneI
aminohydantoin, y d 4%, mp :262-2640 (decomp., from
alcohol.); 1-(5-nitros8lenenal-2)afiiino-2-thio dantoln,
Yi?fi 95%, mp, 24.3-250 (decomp., f-rom alcoholl; and
I- IV ~-(5-nitroselenienyl-2)allylideheI amino-2-
th dantoln, yield 93%, mp 265-2670(decomp., from
acetone), respectively.
ff N-CO
Cfft
02N-VL
(IV)
Card.3/4

Chemistry of Selenophene. XXIV 77358
SOV/79-30-1-19/78
HN-co
S(; Alit
+11.N-NC8NRG0~1f, 0214
(V)
There'are 4references, 2 Sov-iet,-2 Japaneae.
ASSOCIATION: Moscow State Univ ,ersity (Moskovskiy gosudarstvennyy
universitet)
SUJIMITTED: January 5, 1959
Card 4/4

5.36oo.
SOV/f9-30-2-11/(8
AUTHORS: YurlyeV, Yu. K., Rozantsev, E. G.
TITLr,-- Catalytic Converalons -01:' llatevocYclio Compounds. LV.
Synthesis of 2,~-Dimethyl-3-Alkyl- and, 2,5-Mmothyl-
3-Arylthlophaneti
PERIODICAL: Zhurnal obstichey klilmit, 1960, Vol 30, Nr 2, pp 406-
41o (ussR)
ABSTRACT: The authors converted 2,5-dimethyl-3-alkylfuranidines
into corresponding 2,5--dimethyl-3-alkylthiophanes
(aluminum oxide or thorium. dioxide were used as catalysts
t 7700- the space
for the reaction which,was conducted a, ~.~i P
*
-
. Constants
hr
Velocity of hydrogen sulfide was,0.3
and yields of the obtained (new) products are listed ir
Table A. (1).Name of the comp' ound; (2) bp (pressure In
mm); (3) found; (4) calculated; (5) Yield (in %); (6)
- - 7 2,5-Dimethyl-
Results of analysis for sulfur:(In
,2, Dime thyl -3 -1 sobutyl thiophane;

Catalytic Conversions of Heterocyclic Compounds. 77860
LV. Synthesis of 2, 5-Dime thyl --~~-Alkyl -and
2,5-D'i.mettiyl-17,-Arylthlophanes
-isoamylthlophane; (11) 2,5-Dlmethyl-3-cyclohexylthlophane;
(12) 2,5-Dimethyl-3-phenylthiophane; (13) 2,5-Dimethyl-
benzylthiophane.
Table A. Constants and yields of 2,5-dimethyl-3-alkyl-
I
-(or aryl) thio')riatie
C ard 2/!2,
(.3 j
J.';j I 1' 5' ~,2'9'I
III U2 1.5:0~ 0.978.3 65J5 64.81; 21,414 15,22, 15-54
The catalyst 13 thorlum oxide on alumina (251/16' of ThO
2)'
20
n M
. 3 1 4
210--2110 1.4757 U.SWO 515.110 54.18 26 fS.34 18.61
04,B) __ _,__ __ M37
9 20,S-209 1.4740 0,8922 5 4.217 ML18 36 18.33.- 18.61-
t 7521 ~ 1 18.3 1
9 2:17-2138 JATM 0.8868 58-09 58.80 22- 17.20
(M5) 16.97

10 233 1,V
1A 73C O,Si(;2 59.07 58M to Itimt, 17.20
7.5 1) l(;.9.-3
'
I 17-11 B 1.5501 1.0 tO2 6.05 61-71 35 15-FA 16-1(
)
fm)
95-96 1.5650 t.0260 (; 1.05 C(U10 11,20* W.29. 16.07
W.:14

0
11 U ty 1,C 01' 0
0 -2 -11 /f8
'11'T!j)O1M(k3. LV. Syntl ;L..-; Oil' 4"l)-DI
yl- Lrid 2,1~-Dimethy,-`-
-A L-Y D; I 1.10pha I I es,
Tt ~jt,.10 noted thit the ~-,pee(l 1'or- the catalytic reaction of
r)-uft-yjTu-ffa-n-id ijr-i e--l-u-0 1-t-tha-t 'ur the
th-Y-I
2, 5-dimethy I copyl Vuran idine . This I,- explained by
-e~,lc hindvatice cauz -1 by tile -longer jjutyl radical In
t - 13e~ L
s
tile 1~~ -pol.'.I~tlcin to the Vill."Itildirle (,-Ycle und In tr,zjn,,3-
po"litlon to thQ rX,~ -v."WILcul (oce Pig,.' 1-1). Duc. to the
side L,cactiono (dehydi,ation and elimination of. 1123 from
the 1. rite r-mediate 1, 21 -rite ve aptooxy _c ornpound) , the yields
of' 2,5-diaietliyl--,')-aryltlilophot-ie:3 are very low. For these
C0111i)OLITIC111 (5ee note to Table A) t-h *orturn oxide wtas found
to give bettel. ytel(lo than alumIna. Theve ave Y CLLrur-cs;
__._l table; and-14 ~-efevcnces, 12 Soviet, I Jap~inese, 1 U.S.
The U.S. refePence is: D. Rank, N. Sheppard, G. Szasz,
Card j. Chem-. Phys., u~51 (1950) -

"arm
NOW"
y-(86 L
(9
5. -i4oo
yu. K-j 7-efil'ovl Shteynman, A, Gurevich,
AUT11ORS: yurlyev,
of 2-1~,ethyl-
Udy 0 Ox Ide
T-1-711E. and
2 p 411-
Zhurnal Iobshchet khimii, 1960, Vol 30, Nr P
PERIODICA--
415 (USSR)
sized'1,1-dimethYl-l-(5-methi,~ifuryl-2)
ABSTRACT: The authors synthe -1-(5-ethylfuryl-2)
-x (1) and 1,1-dimethYl.
butanone / oxide with 2-methyl-
-3 (11) by reactling mes.tyl
butanone I emonstrating that the
and 2-ethylfuran, respectively, d ~thy3'vinyl grout) 01
3 me
furan ring can react with 01 di
etonjs (bee scheme A).
the CL unsaturated k
Card 1/5

7778F~l
Study of the Furan Series. ITI. Re-
action of 2-Methyl- and 2-Ethylftiran
with Mesityl Oxide
CHS" if C11
C=Cli- C-CfJ3 :Z~ Z51il~--c-oll R-
CV CH3
C11
RJ
C(C"J)r-CH=C-CH3 CH3
s!lcheme A
This reaction wa,~ conducted in a roi.tnd-bottoin flauk
provided vilf-h a mtxev and a condenner, Tile
reaction mixture (the reagent~j weve dissolved In hydro-
quinone) was heated for, 8 hr an the water bath. The
reaction mass was then diluted with ether, washed with
sodium carbonate and water-, and dried over CaCl.- -The
best catalysts were found to be concentrated sulfuric
Card 2/5 acid and boron trifluoride etherate. Repeated dist~111-

Study of the Furan Series. III. Re- 77861
action of 2-Methyl- and 2-Ethylfuran SOV/(9-30-2-12/78
with Mesityl Oxide
ation yielded the addition products. Characteristics of
1,1-(Ilmettiyl-l-(5-rnei,I'Ylfuryi-2)bu'uanone-'4 (I): bp 1006-
2o 20
-1070 (15 Tam); nD I . 4'tOO;Idj~ 0.9723; Its Bernicarba-
o, Tap V-,4-8initvophcnyl-
,&one, white leaflet,
hydvazonc, yellow needles; Tap 109.5-1110 , was charac-
terized by Infvured spectL-um, The 1,1-81methyl-l-
(5-ethylfuryl-2)but'anone-3 (I.T): bp 114 (13 mm);
11D00 1.4682; d1t 20 0.'95'('(; 2,4-dinitropheny1hydrazone,
orange needles; Tap 90,5-910, characterized by Infra-
red spectrum. Reactions-of prepared ketones were studied
on example of 1,1-dime thyl-l-(5-methylfuryl-2)butanone-3.
Scheme B shows the reactants and'the products of the five
Card 3/5 reactions studied.

Study of the Furan Series. III. Re- 77861
action of 2-11fiethyl- and 2-Ethy1furan SOV-79-30-2-12/78
with Mesity, oxide
011)
CHI
VC-1 Cllt-yi-c
I H
C 04. 1
CV13 Oil
L13
V *Y
CH, CH3 m/j
kyll) CH C, -CH'C'-CH, If CHS-n, -CCH, CHI.- CH CH3
H CH3 NHZ
C 0
Scheme B
The constants of the derived compounds6 (1)06, OCdi-
methyllevulinic acid (III): m-0 76--76.5 ~2 1,1-dimeth 1-
1-(5-methyTfury1-2)butano1-3 (IV), bp 106 ~10 mm), n D 26
1-4770, d4 20 0.9690, characterize d by Infrared spectrum;
(3) 1,1-d1met1'Y1-1-(5 -.Methylfuryl-2)-3-aminobutane (V),
Card 4/5 bp 104-105 0 (10 11U11), n D20 1.14580, d1t 20 0.88111; (4) 1,1-

Study of the Furan Series.. Ell R p- - '1778 6- 1
action of 2401ethyl- and 2-Ethyll'uran SOV/79-30-2-12/78
w1th Mesityl Oxlde
--dimethyl-' (5-met1ly1furyl-2)b-atane ~Vl`! bp "15-7"3 r2-0
rl 1-10 1 .215129) d4 200 1, r, I inc tJ:y" - i --ret
D
furyl-2)butanol-3 (Vll): bp 89-900 (6r,-jfr,), nD20 14P-00,
20
d4 0.9703. The authors thank L. A. Kazitsyna for
measurement of spectra. There are 8 references, I
3oviet, 3 German, 1 French, 1 U.S. The U.S, reference
Is Ch. A,, 47, 1.744 (1953).
ASSOCIATION: Moscow State UniversIty (Moskovskiy gosudarstliennyy
universitet)
SUBM'7TTED:
February 4, 1959
Card 5/5

5.34oo,5-36oo,5-3700 71,86:-?

AUTHORS: Yul"Y'ev, Yu. K., Belyca.ova, Z. V., Hoste.-tokly, F. V.,

T IT LE Tr lacy loxyb orane s and Tetvaacetooxygcpmnnium in
of Benzene and Thlophene
PERIODI13AL: Zhurnal obahchey Idiiirij, 1960, Vol 30, Nr 2,
PP 415-1120 (USSR)
ABSTRACT: The authors studied relative acylating ability of mi;,ce,d
anhydrides of various organic acids (acetic, propionic, L~nd
butyric) and inorganic acids, BOW , A1(011) Ge(0111)1, and
3 3 J'
Si(OH)4' The acylation of benzene was performed ~.,iith the
anhydrides formed In situ from the organic acid and the
the nonmetals (boron bromide, gevi'iianlum
-ha.lides, I of
'
tetrachloride aluminum-chloride, and silicon tetra-
-
-
enc-e-of anhydrous
chloride) in benzene solution in pre
o
aluminum chloride. If the latter is absent, the mixed
anhydrides.cAn be isolated. The yields of ',the synth~-oized
Card 1/3 ketones are shown in Table 1.

Tr'lacyloxyboranes and Te'u-raace'o-
maniurn in Acylation of Benzene
iophene
and Th
Table
113/78
SVI//79-30-'-
(M
(A)
613 J(rlo
(D) 66 r. r '2.2 jj)-10
E) 47 al)
M
Z8
nt; (B) Yield of the
to Table 1: (A) Acylating age iatiOn
Key ,H COR (in %); (C) The fix,st dissOc (D)
ketone C6 5 ic acid of the mixed anhydride;
conatant of inorgan- d (boran triacetate); (E)
,&nlc act
(3ilicon t0tVaacet, to.)
Bor,oanhYdi,lde of 01 acid
Silicon anhydride Of OlTan'-(' In tpjacf?,tate
etate; (G) Gel,manil,
CZIT-d 2 /3 (F) Aluminum triac

TrIacYloxyboranes and Tetraaceto-
oxygermanium in Acylation.of Berjzen(~-
and Thiophene
ASSOCIATION:
SUBMITTED:
Card 3/3
77862
SOV/79 - 30- 2 -1
It can be seen that the'acylation capacity of the mixed
anhydrides decreases with decreasing acidity of the
inorganic acid:
Thiophene,111as acylaLed by bovbanhydrideo of acetic and
butyric acids and by germanium tetraacetate (yields of'
acetothienone and propyl-2-thienyl ketone were 68,5%)
using stannic chloride as' catalyst. There are 2 tables
and 20 references, 5 Soviet, 6 German, I French, 1 Finnish,
1 U.K.,,and 6 U.S. The 5 most recent U.K. and U.S. re
referdn'ces are: D. Tarbell, J. Price, J. Org. Chem., 22,
245 (1957); H. Anderson, J. Am. Chem. Soc'., 74 2371.
(1952); Chem. Abst., 41, 5481 (1947); H. Cook, J. Ilet;t-,
B. Saunders, G. Stacey, J. Chem. Soc., 1950, 3125;
J. Johnson, J. Am. Chem. Soc., 73', 5888 (1951).
Moscow State University (Moskovskiy gosudarstvennyy
universitet)
February 9, 1959

5'.36oo
AUTHORS:
TITLE:
PERIODICAL:
ABSTRAM
Card 1/3
78270
SOV/79-30-3-24/69
Yurlyev, Yu. K., Zefirov, N, S.,
Investigation of Furan Series. V. Synthesis or
Derivatives of N-TrichloroTnethylmarcaptoimide of
3,6-Endoxohexahydrophthalic Acid
Zhurnal obshchey Ichimii, 1960, Vol 30) Nr 3)
pp 855-859 (USSR)
The'following two methods were used in the synthesis
of the above derivatives.
R! CU R1 tl~ c0
NH ~0~ \fi-SCC1,
ca It c0
R R
10 10 NH 10 co 'N ti-StC13
) ritpit
o 0~co
C
4t 0
Ull) Un
A,v ct, A,="; e-cl, i,=[", e. or, 0-M., e-MACH,;
R'- H , Rt= CRLOCOCH, ; (Ill
w.

Investigation of Furan Series. V.
SOV/19-3 0-3 -24/6- 9
---The reaction of perchloromethylmercaptan with an
alkaline soluti:on-Of the-imide-of 3-)6-endoxyhexahydro-
phthalic acid or its derivatives is preferred,
because of a high yield (80-90%) of corresponding
N-trichloromethylmerea to derivatives (without
forming the amide salts. The following'compounds were
synthesized: N-trich'Loromethylmercaptoimide of
0
exo 3,6-endoxohyxahydrophthalle acid, mP 15?.5-158 1
U-trichloromethylmereaptoimide of exo-3,6-eadoxo-
&41_ tetrahydrophthalic aoid (yield 83%)., mp 132-132.5 0
N , of exo
-trichlorome thylmcrcaptolxild~ -4,r-dibromo-
3,6-endoxohexahydrophthalIc acid (yield 87%), mp
184-1850; N-trictilovoinothylmex,captoitnide of exo-
4,5,-dichloro-3,6-endoxohexahydrophthalic acid (yield
81%), mp 169.5-1700; N-trichloromethylriercaptoimide
of 3-methy:L-3,6-endoxohexahydrophthalic acid (yield
85%~, mp 148.r-1490; N-trichloromethylmereaptoimide
of 5-dichlor-3-methyl-3,6-endoxohexahydrophthalic
Card 2/3 acid (yield 83%), mp 214-2150; N-trichloromethyl-
mercaptoimide of 3-acetoxymethyl-3,6--endoxohexa-

investigation of Furan Series, V, 78270
SOV79-30-3-24/69
hydrophthalic acid (yield 78%), mP 1580.- There
are 17 references, 13 U.S., 2 Soviet, 2 German.
The 5 most recent U.S. references are% aroxall
W.,-Shropshire- E- Am.-Chem. Sod __75_J,_
5420 (1953); St'oliz' E.) Roge~s C., Ch. A., 46, 9o85
1954); Kittleson A., J. Agr. Food Chem., 1, 677
R95?); Berson J., Swidler R., j. Am. Chem. Soc.,,,
76; iyvwj ~ u;I.Al tlKwart 11. j Burahuk J, 0 J, Am , Chem.
Soo., 74, 3o94 952).
ASSOCIATION; Moscow State University (Moskovskiy gosudarstvennyy
universitet)
SUBMITTED: March 12, 1959
Card 3/3

4"a
3600
5. lil".7 9 - ~;'O -2 5116, 0
so
AUTEMS; K,, z.jytc5uva, Y(.,. L.
of Sc.,lenopht-nc,. XXV.
TITLE:
phene and 4-iiitrooelenophc-iie-2-Carbo.1-ylic A(,1d
PERTODICAl'o ofiohl!boy kJO110-1. -MO, VoI 30, Nr 3, pp ""51Y,
864 (usm)
ABSTRACT: Nitration of P-acetoselenophene yields a mixture of tvic-)
productsi 4-nli~ro-2-acetoselenophene (yield 50%) TnP
123-123-50 and 5-nitro-2-acetoselenophene (yield 8.5x6)
and 2,4-dinl'~ruselenopherie (yleld 41.5%), mp -,(90.
+
Card 1/3

071
Chemistrj of Selenop] tie. XXV. 11-Nluro-
78
2-Acetoselenopherie and 4 -N, .1. t ro s e-1 enoplivne - S 011/7 9 - 3 0 -3) -251//t9
2-Carboxylic Acid
(1/1datloti of with dilute
-ric acId yluldu a ;duvo of )I -III
carboxylic acid and 1[-nlti,os(--Ieiiophene-2-c)-lyoxylic acid,
which on further oxidation with hydroj~en peroxide, yields
acid (yield 30W, mp 1.70-
!'(10. Esterificatlon of this acid yields the methyl
ester of 4-nitroselenophene-2-carboxylic acid (yield 78r'),
RIP 10'.5-1040, and decarboxylation, 3-nitroselenopbene
j
(yield 50,t), raP 77.5-730.
--0N-T-
No,
0
0,,N
Card 2/3

VC1
of 0 r" Po
--2-215169
2 - Ac e to, -8, () V/'f 9 - 3
2-Carboxylic Acid
The ultraviolet absorption maxima, of 4-nitro- and 5-
nitro-2-aceto,3elenophene art,~ 260 inlIand 315 rfl~4 re-
spec, ( tlvely. ~ Ti-iere are 2 f Ipaires; and 11 ref erences, 1~
Soviet, 2 U.S., 2 Dutch, 1 U.K., 1 German, I Japanese.
The U.S. references are: Blatt, A Bach, S., Kre3ch,
L., J. Org. Che~m., 22, 1693 (1957~"
; Fove, W. 0.,
Heffern, J, J., Feldman, E. I., J. Am. Chem.' Soc ., 76s
1378 (1954).
ASSOCIATION: Moscow State University (Mookovskly gosudarstvennyy
univer!,,'tet)
SUBIMITTED: I'March 20, 1959
Card 3/3

..S/079/60/030/05/47/074
B005/BO16
AUTHORS:. Yuroyev, Yu. K., Mezentsovay V. H. V
TITIS: SelenophenoiChemistry. XXVI. 2-Cyclopropyl Selenophene and
2-Fropenyl Selenophene
PERIODICAL: Zhurnal obahchey khimii,-- 16600- V 1- 30t- No. 59- -Pp. 1628-16~1
0
TRET: Ta the present paper the syntheses of-2 cyclo propyl selenophene M
and 2-propenyl selenophene (II) are described. The authors synthesized
(I) on the basis of P-(selenienyl-2-)-aorolein (III). Contrary to a
method used previously (Ref. 1), this compound was obtained by coadensa-
tion of selenophene-2-aldebyde with acetaldehyde in the presence of lye.
By -treating the unsaturated ketone (III) with bydrazine hydrate,
543elenienyl-29-pyrazoline (IV) was obtained. This product was not
isolated but decomposed at once according to the well-known method by
N. 11. Kishner (with platinized carbon and potassium hydroxide). By this
deg:radation, compound (I) results with impurities of a selenienyl-2-
alkene. Compound M was also synthesized from the hydrochloride of
2-(13-dimethyl-amino-propio)-selenophene (Ref. 2) by the action of hydrazine
C ard 1 /3

Selenophene Chemistry. XXVI. 2-Cyclopropyl S/079/60/030/05/47/074
Selenophene and 2-Propenyl Selenophene B005/Boi6
hydrate and Kishner-degradation of theresultant .(selenienyl-2)-pyrazolirie.
-This method- is ~-siiaplet. and more-- convenient than the onadescribed above.
The purification of product-(I) from the __ sele_nienyl_2-~&lkene~ impurity was -
carried out by treatment with potassium pormanganate solution and sub-
sequent working up with 2.4-dinitro-benzene-sulfenyl chloride Contrary
to the unstable monosubstituted pyrazoline (IV) the disubsti;uted
pyrazoline derivative 3-metbyl-5-(selenionyl-20~-pyrazoline (V) obtained
by condensation of selenal-2-acatone with hydrazine hydrate is a stable
compound which is distillable in vacuo without decomposition. In. the sane
way, I-phenyl-5-(selenienyl-2t)-pyrazoline was prepared by condensation
of selenal-2-acetone with phenyl hydrazine. This product melts without
decomposition, On degradation of compound M eacordLing to Kialmer,
2-(20-mothyl-eyelopropyl)-selenophene (VI) results. This product is con-
taminatod by small quantities of selenienyl-2-butene which may be
neparated in the above-mentioned way. The ultraviolet absorption spectra
of methanolic solutions cf compounds M and (VI) show no differences in
-the electron transitions. The spectra were taken on an SF-4 speotro-
.photometer. Compound (I I) was obtained from ethyl-(se1enieny1-2)_c&rbiao1
by dehydration with potassium bisulfate. The initial product was produced
Card 213

Selenophene Chemistryo XXVI. 2-Cyclopropyl s/079J60/030/65/47/074
selenophone-and 2-Proyanyl Selenophene B005/BO16
by an organomagnesium synthesis from selenophone-2-aldehyde and-ethV1
In an experimental partp all operations performed are-described-
in detail. For each of the resultant products# yield, boiling (or melting)
point, refractiveindexq density, molar refractivityp and data of the
ultimate analysis are given. The schemes of the reactions performed are
presented as well. R. Ya. Levina and co-workers.(Ref. 5) are mentioned
in this paper. There-are 6--Soviet references.
ASSOCIATION: Hoskovskiy gosudarstvennyy universitat (Moscow State University)
SUBMITTED: June 12, 1959

NOVITMIT, X.yuj; TUjrR._YU.K.- AIIIMA IYSTA. Tu.A.; BOLISOT, 1.0.;
OIMM, A a r.
Furan series. Part 6: A-ChloroetbylamInee of the fumn
series# Zhur*ob4IChim-- 30 n00722199-2202--Jl 160.
(KM& 13-- 7)
1. Moskovski gosudarstvanWy uni*orsitate
TFurfurylamina), (Thionyl chloride)
(Fa ran)

~S/079/60/030/007/027/039/XX
BOO1/BO66
AUTHORS: Novitakiy, K. Yu.-j 1~olkov, V. P., Koatetskiy, P. V.,
and Yurlyev, Yu. K,
I'LE: _Nerlen. V11. 2,5-Bis(chloro-
T Investigation in th faran
T
methyl)-furan in th Synthesis of 2,5-Bio(alkoxy-met,hyl)-
..and 2~5-Bis(alkyl-mercapto-methyl)-furan
PERIODICAL: Zhurnal obahchey khimii, 1960, Vol. 30, No. 7t pp. 2203-2207
TEXT: Following Ref. I the authors synthesized 2,5-bis(alkoxy-methyl)-
and 2,5-bia(alkyl-mereapto-methyl)-furan by treating 2,5-bis(chloro-methyl)-
furan with alcohols and mercaptans. The substitution of alkoxy groups for
tWD chlorine atoms in compound (I) takes readily place under the action of
alcohols in the presence of alkali lye; the yield of the corresponding
ethers (2,5-bis(alkoxy-methyl)-furans) (11) was between 60 and 70%.
CICH C, 2ROH io ROCH2 CH OR
-CH2 KOH 2
I) -