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

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• Collection: Scientific Abstracts
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• Document Creation Date: November 2, 2016
• Document Release Date: September 19, 2001
• Sequence Number: 14
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

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TMITSY, TU.K.--
Mutual ca .tal7tic tranformations of heterocyclic compounds. low methods
for the synthesis of heterocyclec coinpoundso Uch.sap.Koak, un, I
no,175:159-200 156, (KWA 10: 3 *
(Heterocyclic compounds)

PHASE I BOOK EXPLOITATION 779
Yurlyev, Yur1y Konstantinovich
Pragticheskiye raboty po organicheskoy khimii. fvyp. 11i Sinteazy s
pomoahchlyu tsink-i magniyorganicheskikh soyedineniy, polimerizat-;
siya I depolimerizatsiya polikandensatsiya (Laboratory Work In ---
Organic Chemistry. Nr. 1: Syntheses With Organic Zinc and Magpe-
sium Compounds; Polymerization and Depolymerization; Polycondensa-
tion.) Moscow, Izd-vo Moskovskogo Univ-ta, 1957. 126 p.
12,000 copies printed.
Ed.: Korobitsyna,I.K.; Tech. Ed.: Lomilina,L.N.
PURPOSE: This book is a handbook for laboratory work in organic chemis-
try intended for university students specializing in chemistry.
COVERAGE- This book is the first issue of the series "Laboratory Work
in Orianic Chemistry", based on the laboratory course in organic
chemistry given at Moscow State University in conjunction with the
lecture course "Synthetic Vethoda*of Organic Chemistryn. The lab-
oratory course is considered an independent course rather than a
Card

Laboratory Work in Organic Chemistry (Cont.) 779
supplement to the lecture course. The programs of both the labor-
atory and lecture courses were worked out by the faculty.metmbers of
the Chair of Organic Chemistry, headed previously by Academician
7 The
.D.Zelinskiy and at present by Academician A.N.Nesmeyanov.
N
first issue consists of two parts: "Syntheses With Organic-, Zinc and
Magnesium Compounds" by Yu.K.Yurlyev and R.Ya.Levina; and "polymeri-
zation and Depolymerization Condensation" by Yu.K.Yurlyev. There
are no references.
TA13LE OF CONTENT3:
Foreword 3
SYNTHESES WITH ORGANIC ZINC
AND MAGNESIUM COMPOUNDS
by Yu.K.Yurly-ev and R.Ya.Levina
Preface 5
Obtaining Magnesium Organic Compounds and Their Structure
A C2
Strubture of magnesium organic compound.
Sb~7,ining magnesium organic compounds 9
Car 7

TURITV, TtL.K,; MMHTSOVA, H.90; SADOVAU, Me
Progreso in the chemistry of selenophers. Vest. KoskauneSerovato
makh. astron. f~z, khim. 32 uo.4:201-222 157. (MIRL 11:5)
laafedra organicheakoykhimii Moskovskogo gosudaretvannogo
univeraiteta.
(Selenophane)

AUTHORS-
TITLE:
PERIODICAL:
ABSMACT.,
Card 1/2
Yuryev, Yu. K., and Yelyakov, G. B. 473
Tetraacyloxysilanes in Organic Synthesis. Part 10. Silicon
Anhydrides of Monobasic Saturated-Organic Acids in the Synthesis
of Alkyl-Beta-Vinyl Chloride Ketones (Tetraatsiloksisilany v
organicheskom sinteze. X. Kremneangidridy oditooonowykh
predellnykh-organicheskikh kislot v ainteze alkil-beta-
khlorvinilketonov)
Zhurnal Obshchey Khimii, 1957, Vol. 27, No. 1, pp. 176-179 (U.S.S.R.)
Into the reaction of acetylene taking place in the presence of
anhydrous aluminum chloride, the authors introduced silicon
anhydrides of acetic, propionic, n-butyric and n-caproic acids
and obtained homologous alkyl-beta-vinyl chloride ketones amount-
ing to 30-41% of the amount of acid submitted to reaction. The
yields were lower than the ones obtainable with acid chlorides.
If the acetylene would have reacted not only with the silicon
anhydride but also with the acid chloride which could have been
formed from the former under effect of the aluminum chloride then
the introduction of hydrogen chloride into the reaction mJxture
would have brought a greater yield of alkyl-beta-vinyl chloride
ketone. The reaction of tetraacy loxysilanes with acetylone in

Tetraacyloxysilanes in Organic Synthesis 473
the presence of AlCl was established to be rather an add!Ltion
'Lion of the silicon anhydride saturated
reaction. The addit
monobasic organic acid to the acetylene led to the fcrmaV.on of
orthosilicic acid ester and alkyl-beta-oxyvinyl ketone which under
the effect of AlC13 submitted to cleavage with the resulting forma-
tion of mothyl-beta-vinyl chloride ketone and aluminum halide salt
of orthosilicic Acid. It was assumed that silicon anhydrides of
saturated monobasic organic acids react with acetylene in the
presence of anhydrous aluminum chloride in accordance writh the
Kondakov type reaction (7), i.e. directly, and that the formation
of alkyl-beta-vinyl chloride ketones is due to the cleavage by
ASSOCIATION:
PRE=TED BY:
SUBMITTED:
-AVAILABIS.-
Card 2/2
AlC13 of the initial addition products - orthosilicic acid esters
and Ukyloxyvinyl ketones,
There are 10 references, of which 9 are Slavic.
The Moscow State University (Moskovskiy Gosudarstvemyy Universitet)
February 17, 1956

IM,
MTHORS: Yu. K., and Hezentsova, N. N.
TITLE: The Chemistry of Selenophene. Part 5. Selenophene-2-Aldehyde,
Selenophene-2-Carbinol and Selenophene-2-Acrylic Acid (Mmiya
Selenofena. V. Selenofen-2-aldegidpiselenofen-2-karbFOI- i
selenofen-2-akrilovaya kislota).
PERIODICAL; Zhurnal Obahchey Khimii, 1~57,-Vol.-V.11o. 1, pp. 179-1112 (U.S.S.R.)
ABSMACT: Using dimethylformamide-as a base, the authors syntheoizoda
hitherto unkn4wwn aelenophene-2-aldehyde which is similar it. its
properties to aromatic aldehyde. The formylation of sel,enophene
with dimethylformamide was smooth., giving a 75% aldehyde yield.
Oxidation of selenophene-2-aldehyde with hydrogen peroxide resulted
in the formation of selenophene-2-carboxylic acid; heating of
selenophene-2-aldehyde with acetic anhydride and anhydroas salum
acetate gave selenophene-2-acrylic acid. This acid was also
obtained through condensation of selenophene-2-aldehyde with
malonic acid in the presence of pyridine with consequent decar-
boxylizing of the formirg alpha-carboiq-beta-(2-selenophene)-
=acry1ic=-&c1k I i:--Sel enophene -2-aldehyde . -(when- re*i ced with

Tia-hol~e-rko--Gan-nit~taLr~a-reaction)---~~-
-ebtiditioris ~ofthe
-
fori~abdeh_~e -in
Card 1/2

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YUR!Ut-.': Yxi -K#t--~wWTS"Ao- WjSMIYNVA, T.A. TUSHCHOVA,
tion
and acetYla
The chemistry of selenaphene. ftrt 7: SYnths8l$
d 20-benzoselenophauso.Zhur, ob, Wm#
of 3-arylselOUOPheuGg au (Km 10"g)
27 uo,8:2260-2267 Ag 157.
1. MoakovskiY gosudaratven,~Yy universitato
(Selanophene)

TURIM, Yu.K.; MEZENTSOVA, U.N.; BALASHOTA. T.A.
of selanophene. P4irt 8: M-091onsual-2) - amines,
2-PMnyl-4-081anenal-2)- oiiizolona-5, 5-(selanonal-2 - thiazolidone
-4- thion-2 solonanal-2-rodanine) an4 hydrazathiazolymn salanophene-
2-aldehyde. zhur. ob, khim. 27 no.9:2536-2541 S 157.
(HIRA 110)
laftskovskI7 goeudaretva universitat.
OGlop=

TuRI YEV,ITu.I.; DTATWVITSKAYA. S.V-
in tha SynthasIO of heterocTelic compounds with
two heteroatoma. Part 3: -ar7lthlazolldonea-Z from lr-B-mercaPto
-ethyl) -ar7lamines. Zhur.ob.khim. 27 no.10:2644-2648 0 '57.
(KIRA 11:4)
1,Moakovskiy gosudarstvenny7 uhiveraitate
(Thia'zoldinone) (Amines)

/9-
AUTHORS: Yurlyer, Yu. K.5 S- V- 75-11-49/56
TITLE: Ethyler-e Sulfide in the SyrithGsis of Heterrjcy~;Iic
Compounds 71-ith two Hetarcatcms(nt4-len5ullfid v -~in-.eze
&eterotsiklichosk,Jkh. scyedirerdly s_dvu-,,.iya f..eteroe-tcmam-0
IV. Syiithesis of and 1,T-Aryl-
thiazanes-1 A (IV. Sillte'z
PERIODICAL: Zhurnal Obshchey Xhimii, 1957, Vol. 2'1, fir 11,
PP. 71148-3151 (USSR~
% 'i
ABSTRACT: In the preceding puper the authors showed that N-
roadil,y enter into reaction with
the chlorar.,hydride of carbo-aic acil by formint; 17-aryl,hia-.01-
'done- a I -
--2 vii th y,-; elds off Irt co::nt;'ction wit-h "~A S it
was of intei-est- to imvestiCatc- the behavior of the IT-
lp-mercaptoethyl)-arylal!jj -re~ac'-I'on With
% ineo an analogous 11
dihalides, With 10-33 movable. halveen atomq than in pho7,L-ene-
i.e. wit-h 1 p 1- and In public;a-uiona Jt- is
pointed out that bromethYlene was alreaiy u5ad in t~he
--ondensat'. on wi 'Ih P-aminooth.v) bu t sF.-I ~nris tha
thiazane-1,4 on thaT, occasion fo=3 only iu a amolint,
Card 1/2 The condensation of N-(0--merc-a',pto-

Ethylene Sulfide in the Synthe-sis cf -Hetezoovolic Conpolzads 70-11-40156
With two Hetero~itorrls. !V. Sp,.thesi c ~,f
4-Aryl tttia2ano2-1 0
ethyl)-p-Lolul(jint, j1_(O_jfjt1
N-(P-mero, idine and V,-(P-iaex,captoethyl)-
aptooth -ania
o-anisidivf,j with bromomet~_ylane learls to the formation of a
-~hl.az~lidine-ovclf~ ~vherrj, cxrrespondinEly, 3-phenwvi-v
-tolyl-, and 3-o-tolyl- as well as the
I
hitherto unknovin 7,-o-anisyl-thiazolidines form. The same
reactu_4cn of N-(P-meroaptoethyl)-
'dine and IT-(O-
mercap,",oethyl) --arnisidine viith bromrsthylene cauves the
-ormation c'. ,;L thiazane-,,ro-le -1,4 on which occasion th-~
4-phonyl-i 4- , -tolYl--, 4-i -azAsYl- and 4- --anisy1thiazanes
ar,-- obtained-.
There are 7 r-_,ferences, -31 of 1which are Slavic.
ASSOCIATION: 143scov M-d-veraity Moskovakiy gasudarnt-vennyy universitet
SUBMITTED: November 5, 1956
AVAILABLE: Library of Con,,,-rLiis
1. Cyclic compounds-Synthesis 2. Ethylene sulfide-Chem-
Card 2/2 ical reactions 3- Cyclic cotupounds.-Condensation
reactions

Y LX
AUTHORS: Yurlyev, Yu. X., Dyatlovitskaya, S. V.
79- ~-50/56
TITLE: Ethylene Sulfide in the Synthesis ef Heterocyclic Compounds
With two Het-ero-Atoms (Etilensullfid v sinteze geterotsikli-
cheekikh soyedineniy s dvumya geteroatomaml).
PERIODICAL: Zhurnal Obshchey Khimii, 1957, Vol. 27, 1Tr 11,
Pp. 3152-3154 (USSR)
-ABSTRACT: The authors previously showed that N-(P-marcaptoethyll)-
arylamines readily enter int-o condensation with aldehydes,
phosgene, and bromethylene and correspondinEly form 2-alkyl-
(or 3~-~irY-'~th*-Iazr,!--dc;rcl:~-2~
3-arYlth-~azolidiniio und 4-aulthiazur-es-1A. But
Mercup toe thyl) --arylamine cannot only be uoed in t-.1;.o above-
mentioned coridenaation, i.e. with 2 aff ~.f watt~r,
hydroger. chlor~'de and hydrogen bromido, but also -Ln
condensst. ith sr!"tting off of hydrogen. sulfide,
in the --z!,,iction wifh carb:,n -liotil-fide which should
necessaril- 1~-ad -~c f ormatJor. of 3-31'Ylthi azo' I dinthiozlene-2.
Of the ccmDoundz~ of the thlazol-ldinthion--2 group ho.-'ring
no substittient-5 on the nitroUen-a?,c-m are beat iwi~--stik,-ated,
Card 1/2 the 3-alkyl-(Or wors-k", la the

Ethylene Sulfide in the Synthesis of Heterocyclic 7q-11-Cj0/--j6
Compounds With two Hetero-Atoms
present paper the conden3a+ion of IT-ep-mercaptoethyl)-l
arylamines with carbon disulfide was carried out. This
condensation led to 3-arylthjifizolidir-th2Loneiip-2, which
convincingly iridicai~-es the hiCh reactivity of P-ar..'no-
mersaptan, arylated on iatro--en, intrcdueed by the zttutho,,*2
into the reaction (see fonnula). By conversion of 3-aryl-
thiazolidintlhions--2 t,7- the oorre~lpotiding
by cercu-~~io ox ide their stiucture vea~j 1,rovedl,
There are 13 references, 5 of whioh are Slavio.
ASSOCIATION: 314-)scow Rtat- Veiversity Noskovskly goaudarst-rennyy
ImiVersitet. ) -
SUBMITTED: November 12, 1956
AVAILABLE: Library of Congress
1. Cyclic compounds-Synthesis 2. Ethylene sulfide-
Chemical reactions 3. N- mereaptoethyll-arylamines-
Card 2/;-, Condensation reacticl~:, 4Aarbon disulfide-
Condensation reactions

AUTHORS:
TITLE:
V
Yurlyev, Yu. K., Mezentsova, 11. N., 79-11-51/56
-V-a5-rFo-Y-sF1-y,V. Ye.
Chemistry of Selenophene (Khimiya aelonoteria).
IX. Condensation of Selenophene-2-Aldehyde With Methylketonon,
Synthesis and Reactions of 2-Methylselenophene-5-Aldehyde
(IX. Kondensatsiya aelenofen-2-al*deeida s metilketonami.
Sintez i reaktaii 2-metilselenofen-5-alldegida).
PERIODICAL: Zhurnal Obshchey Khimii, 1957, Vol. 27t lir 11,
Pp- 3155-3160 (USSR)
ABSTRACT: In the present paper the authors continue the investigation
of the reactivity of selenophene-2-aldehyde in examples of
its condensation with methylketones. Its condensations with
methylketones proceed smoothly and lead to the formation
of unsaturated ketones which possess the selenophene-cycle.
In this manner the following compounds were obtained:
selenenal-2-acetone, x-(selenenal-2)-acetophenone,
a-(selenenal-2),;7-methylacetaphenone, I-pherYl-5-
selenienyl-2 pentadiene-1,4-on-3, 1-(furyl-2)-5-
~selenienyl-2~-pentadione-lp4-on-3 and 10-di-(selenienyl-2)-
pen!'adiene-1,4-on-7. The aminomethylation of selonenal-2-
Card 1/2 acetwle according to Mannich (Mannikh) leads to the hyd--o-

Chemistry of Belenophene. IX. Condensation of Selenophene-2- 79-11-51/56
Aldehyde With Nothylketonea. Synthesis and Reactions of
2-Metli.ylselenophene-5-Aldeh.yde
chloride of 5-dimethylamino-l-(sele,-iienyl-2)-pentene-
I ons-3. The redixetion of selenophene-2-aldehyde and
2-methylselenophe-,ie-5-aldehyde according to Kizhner leads
to 2-methylselenophene and correspondingly to 2,5-dimethyl-
selenophene, The condensation of 2-methylselenopliene-5-
aldehyde with hippuric acid, rhodanine and malonic acid
correspondingly yields 2-phenyl-4-(2-methylselenenal-5)-
oxazolone-5,lrl-(2-methylselenenal-5)-thiazolidone-4-thion-2
and P-(2-methylselerophene-5)-acrylic aci&. The condensation
of thioGemicarbazone of 2-methylselenophene-5-aldehyde with
chloroacotic acid loads to tho hydrazothiazolinone of
There are 4 all of whinh aro 01tivia.
ASSOCIATION: MOSCOW State Uailmrgity (Moskovskiy Cosudarstvennyy iiniversitet).
SUB)jJITT7T)! ?. T ,- 14, 1 P 5 6
1. Selenophene-2-aldehyde-Condensation reactions 2. Ket1q]-ketones-
Condensation reactions 3. 2-MeUqlse1enophene-5-a1de1Vde-
Card 2/2 Synthesis 4. 2-Metby2.ae!3nopt.-ene-5-aldehyde-Condensation
reactions

AUTHORS. Yurlyev, Yu. K., Belyakova, Z.'V., Zefirov, N. S. 79-12-19/43
TITLEt --Tctraacyloxysilaaes in Organic Synthesis
(Tetraatsiloksisilany v organicheskom sinteze).
X. Comparative Effect of Catalysts on the Occasion of Acylation
Reaction of Benzene and Thiophene With Tetraacyloxvoilanes
(Sravnitelinoye deystviye katalizatorov v reaktaii atailiro-
vaniya benzola i tiofena tetraatsiloksisilanami).
PERIODICAL: Zhurnal Obshchey Khimii 1957, Vol. 27, Ur 12, PP. 3264-3270
(USSR)
ABSTRACTi In the present work the comparative effbot of a series of
catalysts in the acylation reaotion of thiopheno with tetra-
acetoxysilane with the mixed anhydride of the orthosilicic
acid and acetic acid is investigated. The cabality of reacting
of the two anhydrides to be exapected was examined in order
to known whether the actual acylation of thiophene, selenophene
and benzene is due to the silico-anhydrides of the organic
acids only or whether also chloroanhydrides participate, since
they also occur on the occasion of the reaction of silicium-
tetrachloride on the siliciumanhydride which has already
formed (see formulael). The acylation of thiophene with the
Card 1/3 above anhydride does not only occur under the presence of

Tetraacyloxyoilanes in Organic Synthesis. 79-12-19/43
X. Comparative Effect of Catalysts on the Occasion of Acylation
Reaction of Benzene and Thiophene With.Tetraacyloxysilanes.
anhydrous zinc beryllium chloride and boron fluoride, with
yields of 25,5-46,5 % but also under the presence of tetra-
titanium chloride with a yield of 93,5 %. The acylation of
benzene with anhydride occurs under the presence of anhydrous
aluminium, chloride, as well an of anhydrous iron chloride. No
acylation of benzene takes place under the presence of an-
hydrous zinc chloride, beryllium chloride, boron fluoride and
titanium tetrachloride. The acylation of benzene and thiophen
leads to the same results in the solvent with pure mixed an-
hydride of silicic and acetic acid, gained from siliciumtetra-
chloride and acetic acid anhydride, also from silicium tetra-
chloride and acetic acid with the same results, which is a
convincing prove that the acylating agent is in fact the an-
hydride. On this basis the acylation process of the thiophen
nucleus could be prove& by means of the mentioned anhydrides.
There are 2 tables and 33 references, 9 of which are Slavic.
Card 2/3,

79-a12-;19/43
Tetraacyloxysilanes in organic Synthesis. casion of Acylation
X. Comparative Effect Of cata vats on the oc
Reaction of Benzene, and Thiophene with Tetraacyloxysilanes*
Moscow State UniverBity
ASsoCIATIONt iversitet).
(j&oskovskiy gosudarstvennyY un
November 22, 1956
SUBMITTED:
of Congress
AVAILABLE: LibrarY
-Ysilanes Synthesis 2. Benzene
TetraacY107 ctions Thiophene - Chemical
Chemical rea
reactions 4- cyclic compolands Chemical
reactions
card 3/3

AUTHORSt L=!Zev, Yu. K.I_Dyatlovitakaya, S. V*9 79-12-20/43
Bulavin,
TITLE: Ethylene Sulphide in Synthesis of the Heterocyclic Compounds
with two Hetero-Atoms
(Etilensulifid v ainteze geterotsiklicheakikh soyedineniy s
dvumya geteroatomami)
VI, N - (Po-mercaptoet;Wl) - qU - Aniline Chloride and its
Condensations with Aldehydes, Phosgenes, Carbon Disulphide
(N - (P-'merkaptoetil) - r - khloranilin i kondensatsii yego
a alldegidami, fosgenom, serouglerodom).
PERIODICAL: Zhurnal Obshchey Khimii 1957, Vol. 27# Mr 12, pp. 3271-3275
('USSR)
ABSTRACT: In this work the reaction between ethylene sulphide and
p - aniline halides was investigated. When using rfr - aniline
chloride the authors obtained N mereaptoethyi)
aniline chloride
H C CH
2 2
+ n - ClC6H41'H2 ClC6H4 11HCH2SH
However, it was impossible to carry out the same transposition
'
Card 1/3 with p bromine or p - aniline iodide: On the
occasion of

Ethylene Sulphide in Sy~th-es:Ca-7-6-:f-fh-e-Te-t-,4-r-,-ody-o)~io--C-oupounds-~79-12-20/43-
with two Hetero-Atoms.
Vi. N - (8-meroaptoethyl) Aniline Chloride and its
Condensations with Aldehydes, Phosgenes, Carbon Disulphide4
an attempt to preciptitate H - (p-mercaptoethyl) -5 - aniline
bromine b means of destillation an explosion occurred at
110 - 115 which was the case also with all iodine compounds
inspite of all possible precautionary measures. Thin in-
stability which both compounds must be explained by the mob-
ility of bromine and the still greater one of iodine which
gives the possibility that further condensations must occur
towards the sulphohydro- and aminogroup at increased
temperature. The spontaneous release of hydrogen halide then
leads to the explosion. The interaction between the ethylene
sulphide and p - aniline chloride thus leads to 11 - (V
-mere apt oe thyl)- ---(K----aniline-ohloride--which--on -the occasion
I)i -_ --(I---------
of oxydation with iodine forms a dihydrate PtPI - p-
chlorophenylamino) diethyldisulphide. N - (P-meroaptoethyl) -
TL__ aniline chloride frequently condensates with fat and
aromatic aldehydes (with formic, proprion, butyric and benzoie
aldehyde) as well as with phoagenes and with carbonic disulph-
ide. Thus, 3 -T - chlorophenyl, 2 - methyl - 3 - JL- - chloro-
Card 2/3 phenyl, 2 - ethyl - 3 - JL- - chlorophenyl - 2 - propyl -

Ethylene Sulphide in Sjntheois of the Heterocyclic Compounds 79-12-20/43
with two Hetero-Atoms.
VI. N -- (p -merea-ptoethyl) .~r-- Aniline Chloride and its
Condensations with Aldehydes, Phosgenes, Carbon Disulphide.
3 -' -i~' - ahlorophenyl , and 2 - phanyl ohlorophony).-
thiazolidind aamall au aluo 3 Tj- -
2 - and 3 ---r - cliloroptionylt)iiazolidinotliiori - 2
which are not described in technical literature are syn-
thesized.
There are 10 references, 6 of which are Slavic.
ASSOCIATION: Moscow State University
(1-loskovskiy gosudarstvennyy universitet).
SUBMITTED: December 28, 1956
AVAILABLE: Library of Congress
1. Cyclic compounds - 3ynthWa P. ("Y0,11.0 0():qp('11r1d:i
Condensation reactions
Card 3/3

20-2--26160
AUTHORSi Xorobitsyna, 1. K. , Zhukova, 1. G. Xuvahinova, V. A.
Yurlyev, Yu. K.
Gaydamovich, N. N. ,,
.
TITLE: Synthesis and Isomerization of Enol Acetates of ~-Furani-
dons (Sintez i izomerizatsiya enolatsetatov p-furanidonov)
PERIODICALt Doklady Akademii flauk SSSR, 1957, Vol. 114, Nr 29 pp. 327-330
(US*SR)
ABSTRAM The derivatives of theenolic form of totrahydrofuranon-3
( P-furanidon) and of its homologues have hardly been in-
vestiRated at all. The authors of the paper under review, in
order to produce the acetylic derivatives of the enolic form,
uued such ketonos of tho A-furanidon series in which only
one single methylone group stands in the U-pouition with
------.r,es-p-e-et--t-0---thq---c-a-rb-o-nyl--g-roUp-.- This-made -it- possible - to- ob-w-
tain onlyGne enolic acetate with a position of the double
bond that was known in advance. Isopropenylacetate was used
as acetylating substance. So farg this type of the inter-
esting ~-furanidon derivatives has not been described.
Card 1/3 The authors of the paDer under review examined the behavior

20-2-26160
Synthesis and I~;omerization of Enol Acetates of Plixanidons
Card 2/3
of these eno 'lie acetates with respect to halogenation and
i5omerization. At chlorine blowing through 2,2,5,5-tetrame-
thylfuranidon-3-enolacetate, or through itasolution in chlo-
roform or absolute etherg there is produced at -5 0 a mono-
chlorine-ketone of the furanidine series, i.e- 4-chlorine-
-2,2,5,5-tetramethylfuranidon-3. This reaction is-of fundamental
importancep but it has no preparational significance. One of
the most interesting reactions is the isomerization of the
thermal or catalytic onolacetate-ketorm into 13-diketones.
Iqtriboroflgoride is let through cooled enolic acetate_a8
-40 to - 20 , no 15omerization takea place, At -10 b0 5
on the other hand, after a certain period cC induction a
turbulent reaction takes place as well as a total reainifi-
cation of the reaction mixture. If the same enolic acetate
is let through a glass tube, which is filled with wadding of
glass and heated up to a temperature of 5000 (but not below)
then anisomerization into 4-acetyl-2,2,5,5-tetramethylfurani-
don-3 takes place. At higher temperatures the yield decreases
from 36-5 % to 5 - 10 %. As a mdter of factp it is split in-
to a ketone and a ketene. The production of a cupric salt
and of the derivatives of the 4-acetyl-2,2t5,5-tetramethyl-

20-2-26160
Synthesis and ISOmerization of Enol Acetates of P-Furanidons
furanidon-3 as well as an intense violet coloring by solution
of ferric chloride confirm its structure. The spectrum of
aboorption of this cupric salt as analogous to the spectrum
Of ftboorption of tlj(j ooprio o4lt of aoetylaootone~ which is
one of the charaotariatia A-dikatonua. Tho oxparlmontal
part of the paper under review describes in detail the ro-
actions together with yields, constants and methods. There
are 6 references, 2 of which are Soviet.,
ASSOCIATIONt Moscow State University imeni M. V. Lomonosov (Moskarskiy
gosudarstvennyy universitet im. M. V. Lomonosova)
PRESENTEDs January 16, 1957, by B. A. Ka.-manskiy, Member of the Academy
SUBMITTED: January 129 1957
AVAILABLEs Library of Congress
Card 3/3

OROIIXOTA
KOROBITSYM, ZMMOVA, I,G.; V
ox~,2,2.5.5~-tetra-alkYl-3-furanidones by, the reductiOu
Syr-theois olt 4- tetra-alkyl-3-furanidones. Dokl. AN SSM 117
of 1~.Jgonitroso-2,2,5, 5- (MM 11:3)
no.2:237.-210 H '57- nny.7 Universitot in* M,V, 1,omonoGovao
1 HoskovsklY gosudarstvo
;;edataVlOnO akademikom A.M. NR9m6YanOvym-
(Furan oompounds)

AUTHORSs 'Yurlyev,Yu.K., Rozantsev,E.G.,and SOV/55-58-1-24/33
G 0 &W f ro-V a-, 3- _- it -
TITLE: Catalytic Changes of Heterocyclic Combinations. LIV. Change of
Trialkyl - Furnadynes Into 2,3,5 - Trialkylthiophanes
(tiitilitithe-skiye-prevrashcheniya-goterotsikU~-heskikh soyedineniy.
LIV. Prevrashcheniye 2,3,5 - trialkilfuranidiAc-iv-'-V~2,-3i5-w--tria~&kil-~--
tiofany)
PERIODIGALs Vestnik Mookovskogo universiteta, Seriya fiziko-matematicheakikh i
yestestvennykh nauk, 1956, Nr 1, pp 163-ie6 (usu)
ABSTRAM The method of the analytic change of oxygen-containing heterocyclic
combinations in cycles with other hateroatoms was used success-
fully for the synthesis of 2,3,5 - trimethyl, 2,5 - dimethyl - 3
ethyl - and 2,5 - dimethyl - 3 - propylthiophaas out of
corresponding trialkylfurnidynes. The obtained 2,3,5 - trialkyl-
thiophanes are colorless fluids not solvable in water, boiling at
the normal pressure, and having a characteristic odor.
There are 12 references, 8 of which are Soviet, 3 American, and
I Vrench.
ASSOCIATION-.Kafedra organicheskoy khimii (Chair-of Organic Chemistry)
Card 1/2

'3
OV'b
S
1yev, ljozantsev7 E,G, Gribov, B-G-
AUTILTIORS Yur Yu. '.) .by oatalytic Tranuforma-
5,5-TrialkylthiophaneS ti0fanov
TITLE: Synthesis of 21 (Sintez 2,3,5-trialkil
tion of 2,3,5-irialkylfuranidincs 2,3,5-trialkilfuranidinov)
kataliticheskim prevrashcheniYem
oat', lq5f)t Yol III, vr 6,
pLHIoDICAL: Khimicheskalra nauka i promy3hienn
(USSR)
pp 830-831
.roleuj% is
he use of the sulfur-or.-Yanic c0MPou-1,j:; from
T 0
ABSTRACT: portant task for SOvie t scientists ' The different stliges of a
synthesis of 20,5-trialkylthiophanes froln 293,95-trialkyl-
furanidines are shown. Other compounds of this group are pre-
sentea in a table.
There are 7 Soviet references.
Moskovskiy gosudarstNrennyy universitet imeni JI.V_ Lomonosova
AS"OCIATION: (jejoscoq State University Imeni 14.V. Lomonosov)
SUMMITTED: April 30, 1958
Card 1/1

51(3#4) Yurlyov Yu# K S. Gop SOT/
AUTHORS: 55 58-6-27/31
TITLE: The Infrared Spectra of Thiop~aua.and Its Hosologues
(Infrakrasnyye spektry tiofana I yego gomologov)
PERIODICAL: Vastaik Moskovskogo univ4rsitstae Seriya-matematiki. ' makhanikil
astronomii, fiziki, khimiii- 1958, Nr.'6, PP 215 - 2,22 (USSR)
ABSTRACT: As the exact determination of sulphur containing patroleum
fractions is of a great praotiael tnd technological inter4st
V. M. Tatevskiy-and one of:-the authors (Ref 1" tried to ana-
lyze-the Raman-speatrum of-thlophans and of eight of its homo-
logues with the ;!esult,that they.observed In all foompounds in-
vestigated a.characteristio frequeady of 690 im- w1i1ch was
ascribed to the fully sp=etrical oscillation of the 01ophane
ring. On the other hand, the spectra of the sulphides wAth open
carbon ahains show - In the range Votwoon 600 and 700 am-1 -
-also intoftsive linof whiah,are-,asoribed to tho valency osaillaw
tions of the 0-5-bond. (Refs Z-~). Hence, as the Raman spootrus
is but roughly indicative, and as it is difficult to decipher
it in view of its extensive background, the above authors tried
Card 113 to use the infrared spectrum1or identifying the tive-member

The infrared Spectra of Thiophane and-Its ffoikOlOgUss , 507/55-56--6-27/31
oyclio sulphid9s. Besidost publications are'.l&okIzMr of data
on'the infrared-speatram,of the-thiopheAe,homologuosp The
taisk, therefore, consisted- in finding. out. the. chargLOteristics
of the individual,bands of the various oounecting-gToups of
the homologues worth an analysiso The Infrared speatra. were
taken of the representatives of the 2-Alkyl-thiophone range
(alkyl-C2H59 C3"7' C4"9 ) (Fig 1). of the 3-alkyl-thiopheass
(Alkyl-C2a5P Y7' '4'9' '5 H11 r i-C 5H11, C6Hj3; Fig 2)t the
spectrum of the 2.5 dimethyl-thlophanQ, the representative&
of the range of the 2#5 dimethyl-3-alkyl-thiophous (takyl-
CHV C2H 5t C3HV 04H9t '-C4H9# C5H11 -xztd '_Yll Fig 3)- The
fist two ranges, but also the last, show in their spectra a
repetition of various frequencies whiah can be employed for
characterWng the individual compounds. The valency oscilla-
tions Of C-3 are somewhat lower in the 2-alkyl-thl~ophanes
than in the 3-alkyl-thiophones (715-730 and 730-750 cm-1),
With all monoalkylthiophanes the frequency of the annular
akeleton was at 1260 am-1, whilst with the trialkfl-thiophanes
Card 2/3 this frequency amounted to 1250 cat7l. The bands, absent in

The Infrared Spectra of Thiophane and Its Homologuse $07/55-58-1;-27/31
the infrared spectrum of the thiophane itself and ~he bandeg
all but intensive, in the infrared spectrum of the inonoalkyl-
thiophanes in the range about 1370 CM-1, were aonsiderably
with the trialkylthiophones. Furthermore, the inten-
gity-of the-bands in the-rangea g93O-2940 and-2960cm-1 con-
siderably increased with the increase of the nethylene groups
and the mothyl-groups. Investigations in connectiop with the
intrared-spectrum proved that they may be omployed'advants-
geously for an analySis OfL thie-sulphur-boataining Retroleum
fractions for determining the thiophane and ite hom.olbgues
contained therein. The spectrograms were taken by means of the
spectrometer IKS-11. The constant,valuag of the motoalkyl-
-thiophones and the 2-5 Umethyl-3-alkyl-thiophtneji are com-
piled in tables I and 2. The synthesis of the.leat'mentioned
compgunds is described briefly. There are 3 figurep, 2 tableal
and 22 references# 13 of which are Soviet.
ASSOCIATION: Kafedra organipheakoy khimii (Chair for Organic Ch(Imistry)
8UPHITTED: September 19t 1958

save
TUEL IYV, T ROZAMM. N.G. GOMMKOVA
As. Part 54:
..... 1. Of heteroaclic COIIPOUI
atal7tte c to 2.3.5-trl&WltlLi6jfteU69ll
0
on of 2,34-trIaB71furauldInel; 158-
Mogk.unsSeraimat astronvefir-eekhIMO 13 no 1:W" U-11)
,Omekh. (mntA
kilimij gookovskOgO F,05, univereitOtas
(rurau) (2hiophene)
ME
alli- H

'fu re Yet,; ya'Y",
AUTIRORS: Yurtyev, Yn. Y., Belya,~ova, Z. V. 79-1 - 1/63
TITLE:
PERIODICAL:
ABSTRACT:
Card 1/3
Tetraacyloxysilanneo in Or,~;Zznic Synthesiz Nctraatsilo~_,i-
silany v or;,anicheskom sinteze)
XIII. Synthesis of N,N-Diethylamid- and N-tr,,11amid Acid's
With the Aid of the Silicon Anhydridet; ar.;dur,-Ateod iinr~oIrtc-i,-, OrUalic
Acids (XIII Sintez 11,11-dietilamidov i 1,arilamidov 1-islot -1
pom-c-shchlyu !'renneangidridov predellnyl:h odnoosnovnykil
-orgunicheskikh kis-lot)
Zhurnal Obahchey Yhimii, 1956, Vol. 26, Nr 1, Pp. 3-6, (USSR)
In connection with earlier foreign works the authors in the
present work for the synthesis of 11,IT-diethylamides and if-
.-arylamides uced.tatraacyloxysilanes - mixed anhydrides of
orthosilicie acid and organic acids. These latter had been
successfully utilized by K. D. Petrov in the acylati-,~ri of
aromatic compounds (of benzene and toluene) instead of an-
hydrides and chloro-unhydrides of acids. The authors
adopted the same co-rze in the acylation of heterocyclic
compounds - thiophenep selenophene, pyrrole and indole, as
well as in the synthesis of aromatic a, uncaturatee

Tetraacyloxysilanes in OrGanic Synthesis 79- 1 - 11163
XIII. Synthesis of 11, 11-Diethylamid- ane' 11-Arylamid Acids With the kid of
the Silicon Anhydrides of Saturated -IlonobaBlc Oroanic Acids
ASSOCIATION:
Cz!,rd 2/3
acids. The reaction of the silicon anhydrides of monDbasic
or&anic acids with secondary aliphatic amines may serve as
a convenient uiethod.of synthesis ol' 11,11T-dialkylatiid acids.
According to this method the authors obtainod tho N,ITs-di-
ethylamidea of acetic, propionic, n-butyric, n-valerianic,
isovalerianic and caproic acida witn good yields (6o-qo-,,).
By the acylation of aniline end met~ylaniline with the -aid
of the anhydride of silicic and acetic acid it yta2 ollovin
that the N-arylamides can be synthesized in this manner. In
the synthesis of N-substituted acid amides the use of tetra-
oxysilanes has preference over the chloro-anhYdride or the
.anhydrides of acids. The process of reaction of aniline with
tetraacetoxysilane is represented in the follo-iin-- Tanner:
R
A
,C 6H51111P, I + (C113coo)4Si 4C6H5k-COCH 3 + Si (oil)4 where
R' = H, CH 3' There are 22 referenoco, 1.) if' vh~ch arc, Slavic.
Moscow State Wversity (1-iookovs!,,iy -r)-ud~i.rstvennyy
universitet).

'63
AUTHORS: 'T r1yev, Yu. K., Zhu-'-ova, 1. G. 79-1-2/
TITLE: The Catalytic Conversion of Heterocyclic Compounds
(Kataliticheskiye prevrashcht--niya- L:eterotoiklicheskik'h
-oyodineniy)
LIII. The Converai-ni of Oxazole J1omoloL--,-,nes tD Thiazole
HotioloEues (LIM Prevraahcheniye gomolo,3ov oU9;-,7.olv, v
gror-iologi tiazola)
PERIODICAL: Zhurnal Obahchey Khimii, 1958, Vol. 28, 1Tr 1, pp. 7-11
(USSR)
ABSTRIXT: The reaction of oxazoles with hydroE;en sulfide whhic'
should lead to the corresponding thiazoles was not in-
vestigated. But this reaction, includinj3 the derivatives,
is of hiGh interest for the characteristic of the oxazole
cycle. The formation of thiazoles from oxazoles in thir,
convereion miCht confirn the chemical proxii;iity of the
a
-illy cimilar c~rclic aycteis to their cyclic,11y
atructur.
linked oxygern- atomv The-invout-i-6wtion performod by the
authors of the catalytic conversion of--the-m-thyl homo-
Card 1/3 loGuea of oxazole under the influence of hadro-en oulfide

Tho Crttalytic Conver_,Jon of Heterocyclic Com.-polindo 79-1-2/63
LIII. Tho Converniori of OX-Lizole I(OL1010,V60 to 'I'll 01 fr flow-.01r), flef;
sbowed that the alkyloxazoles, like other five- and six-
-membered oxygen-containing heterocyclic compounds of an
aromatic or alirihatic nature, are s,.:bjcct to a General
,reaction in which the cyclically bound oxy~;en is replz,ccd
by sulfur. The isomeric dimethyloxazoles (2,4-, 2,5- and
4,5-) and 2,4,5-trimethyloxazole under the influence of
hydrogen sulfide upon them in connection vrJ 'th aluminu-;i
oxide and at elevated temperatures, like other five- and
six-membered oxyGen-containing heterocycles, undergo a
oubatitution of the bridge hydrogen by sulfur, where the
corr6dpondin.- dimethylthiazoles (2,5,and 4,5) and 2,4,,5-
-trimethyla2ole are Produced. The catal.-tic conversion of
the oxazole-cycle to the thiazole-cycle takes place iii the
manner as the analoL~ous conversion of furfurane -to
thiophene *--But -it-became evident -that-the oxazole cycle is
much more resistant than furfuranelwith regard t6_the-
action of hydrogen oulfide under these conditions. There
are 8 referencesi 2 of which are Slavic.
ASSOCIATION Moscow State Uhiversity Noskovskiy gosudarstvennyy
Card 2/3 universitet)

-AU THOR S Y VV-, .-Y,
A.-r" Sadovaya. N, K, -3-12161
79-28
ra TLE: Selenophene Chemistry (KhimfYa aelenofena)
X. Synthesis of zhe 3-methy'~-sel-enopher~e-2-Aldehyde and
293-as Well as 2~4-DimettYlselenophene
(X. Sintez 3-metilselencfen-2-alldegida i 2,3- -4 2~4-
dimetilselenofena)
PERIODICAL: Zhurnal Obshchey Khimii, 1956, Vol~, 28, Nr 32 pp. 620-624.
(USSR)
ABSTRACT: In the iodination and reaction with metallo-organic compounds
of the selenophene Aucleus in 3-methylselenophene and 2,4~-
dimethyleelenophone (Ref 3) the authors annumed in
consequence of the analogous structure of selen-s- and
thiophene that there must be also an analogy with respect
to their chemioal properties. Therefore they assumed
a priori that in the 3-~aethylselenophene the substitution
of hydrogen by iodine ia accompanied by the formation of
2-iodo-3-methylagi-Anophene, Wh4eh after the a,-,tion of
Card 1/3 lithium phenyl and after carbonization converts to 3-methyl-

Selenophene Chemistzy 79-28 -3--1216!
X. Synthesis of the 3-methylselenophena-2-Aldehyde and -
293-as Well as 2T4-Dimethylselenoph6ae
selenophene--2-carboxylic ac-id. They alac concludqd that in
the iodination of - 2 4 -,dime thyAl eel enophene the oubsti tuticri
of *drogen by lodinu in tho pooition .5 of tho nuol6ua tctkf)~i
place at a formation of 5-iadQ-2~, 4-dime thy In o1 s~rxophetvt---
Therefore, after its metal reaction and carbonization they
attributed to the final product the structure 2,4-dimethyl-
aelenophene-9--corboxylic acid. The proof had, h~we-fer, to be
given that in the presenf;e of a methyl groupin the position
3 of the selenophene nucle-as halogenation and merourization
actually take place 4-n the position 2 and that also with
4-dimethylsilenophene, this substitution reaction takes
2,
place in position 5. In the present work convincing proof
is furDished for this orientation with regard to 3-methyl-.
and 2,4--dimethyloelenophene in the iodination and
merourization~ For the 8.yntheais of 2,4--dimethylselenophene.
the autho~-a used the 2-mLthylpentene-3, which was added to
the reaction with selenium dioxide in the presence of chromilm
oxide and aluminum oxide., as well as to the reaction with
metallic selerium (&ee mentioned reaction proov~ss),, From
Card 2/3 this can be seen that f roin the ritep:-by-step proce3s only

Selenophene Chemistry 79-28-3-12/61
X. Synthesis of the 3-methylselenophone-2-Aldehyde and
2p3-as Well as 2,4-Dimethylselenophene
one 294-dimethylselenophene could be ohtained, For the
synthesis of 2;3-dimethylsel6nophene the 3-methylselenopherLe
was used-the formulation of which leadsto an aldehyde
to which the structure 3-methylselenophene-2-aldehyde was
attributed; this could be supported by experiments. This
aldehyde converts to 3-methylselenophene-2-carboxylic acid
in oxidationg and to 3-methylsei'.enophene-2-carbinol In
reduction. In the investigated reactions of halogenation,
mercurization and formrlation of 3-met-hylselenophene it
was also proved that the substitution of hydrogen takes
place in the position 2 of the selenophene cycle (see
formulae).
There are 8 references, 7 of which are Soviet,
AO 41AAY A MT^'KT
!!oakovskiy gosudarstvennyy univeraitet
(Moscow State University)
SUBMITTED: February 4, 14957
Card 3/3

Yurlyev, Yu, K.; Dyatlovi-kkaya, S, V. 79-28-4-6/6o
TITLE: Ethylene Sulfide in the Synthesis of fleterocycliG
Compounds With 2 Hetero Atoms (Etilensulifid v sintoze
geterotsiklicheskikh soyedineniy 9 dvumja geteroatomami)
VII. 3-Aryl Thiazolidine-2-Carboxylic Acids and Their
,Der4 -vatives (VII, 3-arilti.azolidin--2-karbonovyye kisloty
i ikh proizv-odnyye)
PERIODICALs Zhurnal Obahchey Khimii, 1956, Vol. 28, Nr 4,,
PP,. 875-88o (USSR)
ABSTRACT: The chemistry of thiazolidine and its derivatives was
studied specially and in detail with the example of
thiazolidine-4-carboxylie a~aid, which forms an essential
part of "he structure of the penicillin molesule. Howevert
thiazolidine-2-carboxyll.o acid itself as well as its deri-
vatiyes viere unknown until very recently. In one of the
previous works the authors demonstrated (Ref. 1) that
N-(O-meroapto ethyl) aryl amines easily condensate with
ITI-dihalogen alkyl and form 3--aryl thia-zolidine. In the
Card 1 3 present work an analogous condensation with dichloro-

Ethylene Sulfide in the Synthesis of Heterocyclic 79-28-4-6/60
ComDounds With 2 Heterr, Atoms. VII. 3-Aryl Thiazolidine.-
2-Carboxylic Acids and Their Deri7atives
acetic acid itb amide and ether was carried out on the
Occasion 04' which the corresponding 3--aryl thiazolidine.,
2-,-arboxylir, acids, their amides and ethers, and from the
latte.- hydrazide3 were obtained. Conclusion: 1) Inter.
action betirfee'r, u-'(6-mercapto ethyl)-aryl amines and dich.:
loro-aceUl,,- acid leada to 3-ary-1 thi,ixzo.'I,idine-.2--carbo.Vlj.c
arids not deu~,ribel in t~;~,hnic;al, 1J.-Ilerature. By this Method
.3.-phPny1_w-;3-7!-roly1 and X,-1(---niay'L t hiazo I f dine -2 --carboxylic
d 2) Condensation of N-(A -mereapto
aej. wei~a ottaine
ethyl)-aryl with dichloro-acetamide which takes place in
analogous way leads to amidea of the 7-aryl thiazolidine-
2-carb,axylic a,,---do which are not described in techni-.al
.literature. By this method amides of the 3-phenyl-,, 3-!
..tolyl-I 3o-tolyl-, 3-IE-anisyl and 3-o--anisyl thiazoli-
dine-2-carboxylic acids were obtained-. 3) CondensatiOrL
of the N-((~_mercap-,c ethyl.)-aryl amines with ethyl ether
of the dichloro acetin acid leads to ethyl ether 3-phenyl-,
3-jE-tolyl-, 3-2L-anisyl- and 3-o-anisyl thiazolidine-2-
carbo--cjlic acids not described in technical literature
and which pass into their hydrazides under the action of
Card 2/3 the hydrazine hydrate.

Enylene Sulfide in the Synthesis of Heterocyclic 79-28-4-6/6o
Compounds Uith 2 Hetero Atoms. V11. 3-Aryl Thiazolidine-
2-Carboxyl-lc Acids and Their Derivatives
There are 2 tables and 1 reference. which is Soviet.
ASSOCIATION: Moskovskiy gosudarstvr-nnyy universitet (Moscow State
University)
SUBVITTED: March 14, 1957
Card 3/3

AUTHORS2 Yar 1yev, Yu. K., Uakarov; ff., Be 79-28-4-8/6o
TITLE: 1,4-Oxyketones and 1,44 iketones in the Catalytic,Synthesis
of 6~ -Pyrroline-,, 4;4-Dihydro-Thiophene Homologs and of the
and Thyophene Homologs Respectively (1,4-oksike=
toli~ I : .4-cLiKet-ony v katali ticheskom sinteze gomologov
10~-pirr~lina, 41--digidrotiofena i sootvetstvenno gomologov
pirrola i tiofena)
PERIODICAL-z Zhurnal Obshchey Khimii, 11958. Vol. 28, Nr 4,
PP- 885-891 (USSR)
'ABSTRACT; As can be seen from previous papers (Refs. 1-8) saturated
as well as unsaturated 1..,4-diols are introduced in the ca-
talytic synthesis of 5-membered heterocycles~ On this occa-
sion the double or triple binding had the central position
in the case of the latter. and it was between the second
and the third carbon atoms in this system of four carbon
atoms. In this connection it was of interest to introduce
the most simple 194-katone alcohol as well as 1,4-diketone
into the described synthesis. These are bound to react in
Card 1/3 joint catalytic dehydration with ammonia, with amines or

1,4-Oxyketones and 1,4-Diketones in the Catalytic 79-20-4-0/6o
Synthesis of eY-Pyrroline-i 4-1-Dihydro-Thiophene Homologs an(L Of
the F7rrt~.e and Tki!qphene Homologs Respectively
with hydrogen sulfide in the enol form like unsaturated
diols with one and correspondingly hydroxyl groups with
the carbon atoms of double bond. In the present work the
authors used -acetopropyl alcohol as representative of
the 1,A .' oxykSones. It reacted like pentene-2-diol.-2,5
in the onol form under the action of ammonia in the pre-
sence of aluminum oxide at increased temperature, and
produced the 2--methyl-67--pyrroline (50%) under the action
of aniline-l-phenyl.~.2--methyl.-,81-pyrroline (58%) and under
the action of hydrogen sulfide -2-methyl- A2,-dihydro tiophene
(38,5%) (Ref, 9). It was found that in the reactions descrim
bed the precipitation of water and the closing of the nitro~-
gen or sulfur containing cycles takes place directly by
means of joint catalytic dehydration of ammoniap the amines
or of hydrogen sulfide as well as of the 194-diols and also
of the IA-oxyketones or 1,4-diketones in their enol form.
Consequently the formation of 2-methyl- 61:.dihydro-furan is
no obligatory intermediate stage in catalythic synthesis
of 2-methyl- 616--pyrroline from 91-acetopropyl alcohol and
Card 2/3 ammonia. Conclusiont 194-oxyketones and 1,4-diketones can

1,4-Oxyketones and 1,4-Diketones in the Catalytic 79-28-4-6/ o
Synthesis of 4"-Pyrroline-, &-.Dihy&ro-Thiophene Homologs
and of the Pyrrole and Thyophene Homologs Respectively
be used successfully in the catalytic synthesis of
5-membered nitrogen- and sulfur containing heterocyclic
compounds. The joint catalytic dehydration of sr-aceto.
propyl alcohol with ammonial aniline, and hydrogen sula
fide in the presence of aluminum oxide at 325-330 0 re=
presents a good method for the corresponding synthesis
of 2-methyl- &-pyrrolineq 1-phenyl-2-methyl- 6%.pyrroline,
and 2-aethyl- 42--dihydro thiophene. In the case of joint
catalytic dehydration of acetony-lacetone with ammonia and
hydrogen sulfide at 3250 in the presence of aluminum oxide
the corresponding_2,5--dimethyZ_pyrrole,--I-phenyl-2,5-dime.-
-thyl pyrroleg-an-d 2-,5-dimethyl thiophene form.
There are 3 tables and 28 referencez, 17 of which are
Soviets
ASSOCIATIONs Moskovskiy gosudaratvennyy universitet (Moscow State
University)
SUBMITTEDt March 2op 1957
Uard 3/3

AUTHORS:
-28
yako'v G-. B 79 -5-41/69
__~~_o ~Osov~,A.
TITLE: 1b1.'raacy1o)q-q-ilanes _'n Organic Synthesis
(Tetraatsiloksisilany v organicheskom sinteze).
XIV. Synthesis of Homologs of Unnamic Acidkof
o( -Alkyl- 13 -Phenylacrylic Acids)
CXIT. S.-ntez gomologov korichnoy kisloty (0(-a1kil-',6 -
-fenilakrilovykh kislot)]
PERIODICALt Zhurnal Obshchey Khimllip 1958, Vol.w. 289 Nr 5,
PP, 1302-1 3o6 (ussp,)
ABSTRACT: In the previous paper it was reported (reference 1)
that tetraacetoxysilane the mixed anhydride of
eilicic and acetic aoid can be used successfully
in place of acetic anhydrida in the synthesis of
aromatio o~ /12 .-unsaturated acids according to Perkin.
This silane enters oondensation with benzaldehyde in
the presence of usual condensing agents, anhydrous
soditim acetate as well as potash, in which case cinnamic
Card 1/3 acid is not obtained in smalle-. yields than in the, f,,age

4
%btraacy;oxy-qi1anes in Organi., Synthesis. 79-28-5-41/69
XIV. Synthesis of Homologs of Cinnamic-Acid (of OC-Alky-l-
-Phenylaorylic Acids)
of acetic anhydride. It wag therefore of intereat to
use also the sili,-;io acid anhydrides of other
saturated monobasia acids -for the synthezie of cinnamic
acid homolog5j~ In the prevent work the ~illlcio aoid
anhy4rldov at' propri-oni,,,-,butyrle-~ va,."rianic--
isovalerianii,,- and lapronlo acid were Introdvood/on wh1oh
occasion a number :~f ~( , -alkyl-, /~ --phenylacrylic aoid3
were obtained in yields of from 29 - 69;,5 clo (see schr~-me)z,
Thus the siliclo aoid anhydzides uf the monobasic
aliphatic. acids can be -a--ed in place o:f the anhydrides
of the corresponding a--ids in the conden--ation with ,
benzaldehyde, witlh ~(-alkyl*innami(, acids roe-ulting from
it. When, 1-ilic;ic, acid anhydrides of proprioric- and
,Valeric acid, are ueed,,only the -3orresponding cinnamic
a.-I.ds are obtained; ir. the case of the acid
anhydride of isovaler-io aeid the /~--'Lsi:;propyletyrene is
formed as final produt:~t. Wher, using silicic acid
anhydrides of butyric acid and oapronic aoid besides
Card 2/3 d,' -ai-aycinnamio. a,~ids alvo sty-renes are obtained as

Tetraacylo xy-silanes -' in Organic Synthesis 79-28-5-41/69
XIV. Synthesis of Homologs of Cinnamio Acid (ofd/,-Alkyl-/~
-.Phenylacrylic Acids)
side products. There are 14 references, 2 of-which are
Soviet.
ASSOCIATION: Mo8kovskiy gosudarstvennyy universitet
(Moscow State University)
SUBMITTED: April 3, 1957
Card 3/3

All' 11M)
TITLE
A.
'y
Tetrtwyloxysilunas In Organic Synthesip
."lany 7 organicheskom sinteze) XV. Thp Syi~thezlz of C,O-
-Unsaturp-ted Acids of th4.% 'Furfuran- anft Thiophene Seriee
I - a ' f
(XV, ','intez ci,P-nepr~det'nykh k1slot r%! d!-, furfina i
PE-1110DICAL! Zhurnal obshchey khimii... 1958, Vol., 28, '1r 6. pn, 5 1
(USSR)
AB3TRACT- In connection with earlier papera tne authc,-,%~ 1."
Card I
interested in bringing about conderovation -,f -Ierrnaoyllxy-
silanes with other aldehydes of aromatic type, with
furfuro3mand thiophene-P--aldehyde, In or&-Ir t,,, rblvain the
.B-(furfury1-2)- urd, corresporidirteLy,
acid. According to Mar~~kwaild ~.Ref 2) (J.arkralld) C,-(furfur,--1-
-2)-acrylic acid (80 is ob-tained accordinr.: It-,c the wz~uql
re ac. t i'on mathod rea:jmm,.-mded bly Perkirt ':jerkin) 4:X furfurol'?
and acetic zirihvdrido in the off acetic p~-tat-!aium-
There P-re no reports in papers regarding the syntheai,3 of
c(-methyl-~ a-propy).- and a-butyl-o-(Vurturyl-2)-r%cr.,/Iia acid,

Tetraaoyloxysi lanes in Organic Synthesis. XV. 'I'lle "yn- SUV179-2le-6-26116";
thesis of Acids of ti-le and
according tc: Perkin's _eaC~40-. In t
A- _. A he present paper fLip
following acids were synthesized in the performz~d cardensa-
tion -w-f furfurole ,ith silicoti anhydride-sof tht- neet~(~-,
propion-ic-, valleric-, isovaleri-. !trod cqpronic acid:
j1-( furfury1-2)-ac,ry1i-. acid and correspondingly t-methyl-,
a-ethyl-, a-propy-l-, a-isopropyl and a-butyl-~-(furfuryl.-2)-
-acrylic acid, which proved that the fie.]d of application
of tetraacyloxyzilane in organic syntkiesi3 .-art ve extended
(see scheme 'I), The condensation of thiophene-2-fl.dehyde
with siliconacetic anhydride in the iprpnewc,?, of neetic
potassium lead to 0-1'thienyl-2)-ucry1_i(, at,1(1A. This acid had
alreadybeen Produced by Biderman (Biderman) (Ref 7) wi,rh
acetic anhydride in the place of the above mentloned an-
hydride, no yield was mentioned, however. There are 2 tables
and 11 references, It of vhich is Soviet.
ASSOCIATION: Moskovskiy goaudarstvennyy universitet (Moscow state University)
SUBMITTED: May 29. 1957
Card 2/3

AU 'THOR S: Yurlyev, Yu. K., Belyakova, Z. V. SOY/79 -26 -7 -,0/0'4
TITLE. Tetraacyloxy-Silanes in Orj~,,anic Synthesis (Tetraatailoi-oisilany
v orf;anichenkonr nintoT~o) XVI. Bonzoyloxy-Trichloronilane ,.,nd
the nowitivity of tho flon."OY1 Ofro-lip (XV1.Bonzoi1oVsitrik1ilo,r-
py)
PERIODICAL: ZhAArnal obf3lichey khinii, 195B9 Vol. 20, 1Tr 7,
PP. 1755 - 1760 (USSR)
ABSTRACT: In the investigation of the reaction of silicon tetrachlorile
with benzoic acid the authors fou-nd that in the case of an
excess of the former (molar ratios 1,7:1 and 2:1) without a
solvent, and on a heating, within 12 hours with subseqi,,ent vacuum
distillation the benzoyloxy-trichlorosilane (Formula 1) is
obtained almost quantitatively. According to references 2 and
3 or--anic acids form on the action of excess silicon tetra-
chloride at 1500-1600 in closed vesnels the corre::ponding
--- ----chlorine anhydrides and the cilicaLI,el (II) , sicl +41RCOON
g
Card 1/3 2RCOCJ Aria --producti
indtAc t1 -n-of-bCILZO,[~-,
4

w ~LN--"4 I ft'-3 t a 0
Tetraacyloxy-Silanes in Organic Synthesis. XYT. SOV/70-28-7-9/64
Denzoylozy-Trichlorosilane and the Reactivity of the Benzoyl Grou."
chloride-from berzoic acid and silicon tetrachloride is bask.
on this fact. Contrary to earlier assum-Aions, concerning- thiv
reaction process (Schemen III and IV) t'!Ie data of the prer~ent
experiments furnish a much more complicated picture. The
formation of benzoyl chloride is the re2ult of the conversion
of the tetrabenzoyl oxy3ilanc and benzoyloxy-trichlorosilane
forning in the reaction mixture, as well ar) of the oiibnequen';
decomposition of the latter at hi,-Iier temperature. The
benzoyloxy group in benzoylox.-trichlorosilane in r.,iore reactive
than the chlorine atoras and it is more easily substituted by
the etho%y group on the action of ethylalcohol. There are 1
table and 20 references, 11 of which are Soviet.
ASSOCIATION: Monkovakiy gooudaro-tvennyy univornitet (Mooooi--, Ot,~,lto Univ,~,rnity)
SUBMITTED: June 3, 1957
Card 2/3

MT ORS Yurlyev, Yu. K,, S&dovayaj 11, K. S(JV/79,-213-8-34/66
TITLE: Chemistry of Selenophene (Khimiye selanofena) X1, O-Iodo-
selanophenes in the Organo-lodine Magnesium 5ynthesis of
Selenophene-,--carboxylic Acids (XI, CA.YQdselenofen v magniyo:r-
ga;qtcheakom sinteze selenofen-g-karbonavykh kialot~
PERIODICAL-, Zhurnal obahchey khimii$ 1958% Val*. 28, Hr 69 pp, 2162-2164
(Ussa)
4)3!1TB4CT% whoveaQ UMQUawo Naegave) in his paper on the halogenation
Qt th,% selenagone kAucloue (Rot 1). alatims -that 2-hologen
Irk partioular 2-Iodoselenophene, show almost
to arignard N-labyar) reaction with magnesiun, the authors
bave la their present paper, that magnesium can
tax% IcAfte mgmestun eelonaphe4es In dry ether, This re-
havever, requires, an activation of the reaction
xkth ethylona bra-aide and a alaw addition of 2-todoeeleno-
g&em t* nagnestual the other solution boiling continuous-
17. Carbomylation of the resulting 2-iodomgneslum seleno-
rba-men f=%Slakwe the c=reajxmdIng a-carboxylic aelde of thi)
C&3:d. VZ, LvlemaFbexe serlas, which a" Identical with those s5mthesized

Chemla~xy cf Se3expgm&eme. Zr. r-rvdOveI#MhmWv In WTI?9,-2"-34166
the Orgww-ladimrr. Tzg=.zd= Whcomis of
~T' Um PMU=-V Cm Cm ftrUer occasion (rof 2) (Reaction dia-
pun). TU sum tzprfr"t with 2-brazoselonophsite was un-
sIz=Cx-qft,I. Me difirecutiva Constants of "14norkao-2-
mazuvylkq aC14 WA, of bezz8ft sold *Or# detsmifted In 80
atl~rl alcagtol rpt 20 F usiffS a ptontim4tor L.I',-5
* CUSS d1saftwdo, acid
W" 9&,MM tO ft fW - ftftiv &S -804M 90 UNSOIC 0614 (Table 2).
aalftv Thdw6 S" 2 tLiktuir =d .5 refeffe"ag" I of which is
.~4g 1;_
50 1957

,
l
e.
3
Yu
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lenotena
ilimiya !~e
.~rlr Of' 1-elenopaen.-~ uahe. rid -2
seicn
t
ro
_11i
H %nd 5
,Feleno~en-
it,-O
-
ophene
,
e i 5-n
j
_
cn
~,,
,
aegi
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I",
11i trove leno,~
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I
exid
-i -,, 167
-16
4
1~himi 4 p '!oi.
--hchey
ob
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US
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,

en
r,-
Vhe uUtho r.:r!!j cti
of 4, 1,
L
11 ntool b:,, t r_uthors
r,oml , . , , F V
Tn
2,1
.v~.nilide ',, good

-r-
ethyl DO
jj
,
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1E:' 1103)hen,~
d the
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ere
ren
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itrif
its n
t-rif ictit ion O
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-Autt, o
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above diacetate,
!--ld being 66 cv'_-.~nlatod
t'l-,c- yi fo.- the ca_Ieno,_'icnr_--
-
-elillc!wde in~ro,!uccd i1n Mc~ roaction) . By oxid~Wor: -ith
1--otnsrium 'Ach1rivts, gne :-u',fir~,ic !%cili the corre!--un,"irle,
cLrboxylic w::i'd -",o.-:rLd, a,ij IV- ~;st erificatiun --:-ith ni:thyl
alcoho"I its corre,-Ino,~J~j2~njz rvthyl Pz-t~,r _-t!action
The oicLcrninritioyi of -Jie

i..ci(~ ahrj-.-.-A haf j' 4
t n
stron-,_,r than of o-nitro-
There im-, 1 '~;blt! .r.:* o" ","Ai.cil

Orr: 'q.G_d:-o-s~uIziy gosmdan3tvenayy univerz;i-tCA
':RIBMITT'~_'D J111Y.5, !957
rd 2/2

yu. G-9 s0;/79-28-8-36/66
yur I ye, Rozantrle'vt
2 5-Dimethyl-3-plkylfuraniaines (sintez
TITLE, SynthesiB of the t furanidinov)
2,5-dimetil~3-.alkil . 6, Vol. 28, Nr 8t
Zhurnal obahchey khimii, 195
pj,,RjODIGJAL: 66 - 2171 (IjSSR) ,
pp. 21 sis of the trialkyl-
esent paper describea the synthe 1s in the 2,3 and 5-
ABSTRACT- The pr which have the alkylradica yl-3-ethy:L-
furanidines, to in literature on the 2t5-dimeth
positions. Repor Lble (Ref 2). The synthesis is
furanidine only are allils of the 4-ethylhexene-1-0"5
carried out by distillation thesized the 2#j,5-tri-
with phosphoric acid. The authors 5yn ranidone-3 according
alkylfuranidine3 from 215-dimethyl-fu
t6 the folio-,ving_scheme* I Alktl,gX 2 -alityl-3-
2,5-dimethyl-3 112
-3
imetbylfuranido,e ran 1-
215-d 1 U20 -alkyldihydrofil' 5
hydrox-Yfuranidine -'~- 295-dimethYl-3
Card 1/3 J2
M

Synthesis of the 2,5-Dimethyl-3-Alkylfiaranidines SoV/79-26-8-36/66
2,5-dimet)Lyl-3-alkylfiiranidizie. According to this method
2#5--dimothyI-3-ethY!-3-
'hydroxyfuranidine and the 2,5-dimethyl-3-6ropyl-3-hydroxy-
furanidi-ne-which-has not-beon described,_heretofore, were
4. -lkyl 3
synthesized. The dehydration of the 2,5-dimeuhyl-3-a
hydroxyfuranidine produces a mixture of the dihydrofuran
isomers with an admixture of diene hydrocarbons. For the
dehydration of the tertiary alcohols of the furanidine series
iodine and p-toluene sulfonic acid are the best means. The
catalytic hydration of the 2,5-dimethyl-3-alkyldihydrofuran3
3rields 2,5-dimethYl-3-alkylfuranid#ne. The described synthesis
of the 2,1,5-trialkylfuranidines represents a -general methol
of synthe6is of the f~uranidine homologs of this structure.
There are 1 table and 7 referencest 4 of which are Soviet,
ASSOCIATION: Moskovskiy gosudarstvanny-y universitet (Moscow State University)
SUBIMITTED: July 1, 1957
Card 2/3

K=M~-Tf-
MRIUV, TU.K.; BELTAKOVA, Z.T.; VOLKOT, V. P.
Tetraacyloxy silanes In organic quthesis, Part 17: Acylation
of benzene by silicon aabydriden of acetic acid, mono. di and tri-
chlorloacatic anda-bromopropionic acids. Zbnr.ob.khim. 28 no.q:
2372,2376 S 158. (KIRA 11:11)
1. Kookovskly gosudarstvennyy universitet.
(Benzene) (Acylation)

YURIUVO YU.K.; DYATLOVITSKAYA, S.V4
Atbylene sulfide in the synthesis of heterocyclic couTouads with
two hateroatoms. Part 8: Synthesis of 2-(furyl-w2l)-, 2-(thienyl-21)
and 2-(BelenYl-2l)-3-arylthiazolidines. Zhur.ob.khim. 28 no.9:
2377-2380 IS '58. (MIRA 11:11)
1. Moskovskly gosudarstvannyy universitet.
(Thiazolidine)

AUTHORS: t.XurOyev, Yu. K., Belyakova, Z. V., SOY/79-26-lo-27/6o
i~ Ti-ar-0 ~ ~11 -
TITLE: Tetra-Acyloxy Silanes in Organic Synthesis (Tetraatsilokei-
ailany Y organicheakom sinteze) XVIII. On the Structure
of the Silicic Anhydrides of the Bivalent Saturated
Organic Acids (XVIII. 0 stroyenii kremneangidridov dvukhos-
novnykh predellnykh organicheskikh kislot)
PERIODICAL: Zhurnal obahchey khimii, 1958, Vol 28t Nr lo,
pp 2766 2770 (USSR)
ABSTRACT: In connection with earlier papers concerning the syn-
thesis of silicic anhydrides of-bivalent organic-acids
from silicon tetrachloride and saturated bivalent acids
in benzene (Refs 1,2) under the formation of hydrogen
chloride the problem concerning the structure remained
unsolved. Based on geiieral considerations the structure
of a silicio anhydride of the bivalent acid could be
given by the schemes (I),(II) and (III). With reapect
to the experimental results obtained in the acylation
of benzene and thiophene with the above mentioned an-
Card 1/3 hydrides it must be mentioned that only ketonic acids

Tetra-Acyloxy- Sildnes in Organic Synthesis. XV111. SOY/'tq-20-1o-27/6)0
On the Structure of the Silicic ~Lnhydrides of 40he Bivalent Saturat-l~d
Organic Acids
;~ei~,`Ao,h-raccount ketoneat i.e.the symmetrical dibenzoyl
and di(tenoyl-2)-alkanes, were obtained as reaction
products, as it is the case in the acylation of the
benzene nucleus with these anhydrides. The absence
of the diketones in the acylation products of benzene
and thiophene with the silicic anhydrides of the
bivalent acids was regarded as important, however, not
completely sufficient, proof of the 5tructure(III). The
further experiment supplied ample proof of the structure
(III) since the twice smaller, theoretically necessary
amount of hydrogen chlorida formed in the reaction
of silicon tetrachloride with succinic vqid in benzene
medium corresponded to the formation of this structure.
The data of the analyses of the formed silicon succinic
anhydride tend to Drove the structure (III). The com-
parison of the experimental data and the calculated
data in the table shows completely that the silicon
succinic anhydride synthesized from succinic acid and
Oard 2/3 Sici 4 according to the method mentioned corresponds to

29ZMWNWAC~
Tetra-Acyloxy Silanes in Or,,,--anic Synthesis. XVIII- SOV/79-28-lo-27/6o-
On the Structure of the Silicic Anhydrides of the Biv-,lent &~turated
Or,3anic Acids
the structure (III) in which the carboxyl groups are
maintained in each of the four acid radicals combined with
the silicon atom. There are 1 table and 10 references,
3 of which are Soviet.
ASSOCIATION: Moskovgkiy aosud,~.rotvennn universitet (L"Oscow State,
University)
SUEMITTIED,: September 20, 1957
Card 3/13

-kUTHORS: Yurlyev,,Yu.~ K., Vysokosov, A. N., SOY/79-28-lo-28/6o
G oTeM&b7W,--3-. -"-
TTTLE: Tatra-Acyloxy Silanes in Organic Synthesis (Tetraatsiloksi-.
ollany Y organiahookom sintoze) XIX, Synthesis of the
3- and 4-11itro-ftzmatnio Axida and Tfiotr lloi-ftologo of tho
a-Alkyl *-p-(Nitrophenyl)-Acrylic Acide(M. Silitez 3-1-4-
nitrokorichnoy kislot i ikh gomologov a-alkil-p-(nitrofenil)-
akrilovykh kislot)
PERIODICAL: Zhurnal obshchey- khimii, 1958, Vol 28, ITr lo,
pp 2770 - 2772 (USSR)
ABSTRACT: In the present paper the condensation of the sillcic
anhydrides of the saturated monovalent organic acids
with m- and p-nitro-benzaldehyde was carried out.
The following nitro-cinnamic were obtained in high
yields: 83,57* 3-nitro-cinnamic-, 89,Z 4-nitro-cinnamic-,
86% 4-nitro-a-methyl-cinnamic-# 87% 4-nitro-a-ethyl-
nnami-c~.~j -47
loo--4-nitr-of!7-a-.P-roPYl-ainnairic-, 59% 4-nitro-a-
isopropyl~ainnam --- a6d -4;~;-nilro-
Card 1/3 Sodium acetate was used its condensing agent in the

Tetra-Acyloxy Silanan in Org,anio Syntheal"I.M. BOY/79-28-lo-28/66
Synthesis of the 3- and 4-11itro-Cinn-riic At;-4,~'z _atid EcinoloL-a of the
a-Alkyl-p-(Nitrophenyl)-Acrylic Acids
reaction of the m- and p- nitro-benzaldehyde
with silicon acotic anhydride; in the condenSat4ona
with silicic anhydride of the other acids potash
(Scheme) was used. The same behaviour of these an-
hydrides and the anliydrides of organic acids in the
Perkins reaction ir, demonstrated by the fact that their
condensation with nitro-benzaldehyde takes place more
completely and In-ads to higher ~,ields of nitro-cinnamic
acids than of unsubstituted cinnamic acids. The
stabilizing effect of tho nitro group of the carbonyl
component is shown -aithout any doubt in the intermediate
staLge of the reaction where the ester of the ortho-
ailicie acid and of the a-alkyl-p-(nitrophenyl)-p-
oxyhydro acrylic acid (II) formod from the affiliation
product (I) loses-the silic-4.c acid more easily under
the formation of the compound (III) than it is subjected
to the decarboxylation and the separation of silicie
acid under the formation of the nitro-styrene homolog (Iv).
Card 2/3 The condensation mentioned above offers high yields of

Tatra-A4yloxy Silanes-in Organic Synthesis. XILLm SOY/79-28-lo-28/6o
Synthesis of the 3- and 4-ffitro-Cinnamic Acids a`--d Their Homo'-logs of the
a-Ak-y'~-lrj-(.114-trophenyl)-Acrylic Acids
the corresponding nitro-cihnamic acids also in the
case where the silicic anhydride is formed from an acid
with a ramified radical. There are 2 tables and 9 refer-
ences, 2 of which are Soviet.
ASSOCIATION: Moskovskiy gosudarstvennyy universitat (Moscow State
University)
SUBMITTED: September 23, 1957
Card 3/3

AUTHORS: Xurlyev. Sadovaya, N. K., SOV/79-28-11-30/55
Titov, V. V.
TITLE: Tlhe-Chomiotry of Sol C'nophen o -(Khimiya selonofena)
XIII. Cyano-Ethylation of the Ketoneo of the Selonoph-one
Series (XIII. Toianetilirovantye ketonov ryada selenofena)
PERIODICAL: Zhurnal obshchey khimii, 1956, Vol 28, Ur 11,
PP 3036 - 3041 (USSR)
ABSTRACT: In an earlier paper (Ref 1) the authors succeeded
to amino-methylate the ketones of the selenophene
series according to Mannich (Mannikh), which led
to some P-dinethyl-aminoallgl-(selenienyl-2)-ketones.
In the present paper they continue the investigation
of the reactivity of these ketones and attempted to
carry out their cyano-ethylation. The cyano-ethylation
of the 2-acyl selenophenes that do not have alkyl
radicals in the position 3 takes place quantitatively
on the action of acrylonitrile in the presence of an
alkyl alcoholate. In this way the following S-k-etone
nitriles of the selenophene-series were obtained:
Card 1/3 11,11,11-tri(eyano-ethyl)-2-aceto-selenophene,

The Chemistry of Selenophene. XIII. Cyano-Ethylation SOV/710-28-11-3o,/55
of the Ketones of the Selenophene Series
11,11-di(cyano-ethyl)-2-propioselenophene, and
11-methyl-11-eyano-ethyl-2-propioselenophene. The
cyano-ethylation of the 3-methyl-2-acyl selenophene
does not take place, apparently because of the
difficulties in the spatial arrangement. Only in the
cas6---of-the 3-methyl-2-ace'toselenophene-a-xeaction
took place, however, with a smaller yield of
3-methyl-11,11,11-tri(cyano-ethyl)-2-acetoselenophene.
In the alkaline hydrolysis of the ~-ketonitriles
of the selenophene series &-ketonic acids unknown
before in thin series were obtained:11,11,11-tri-
(cirboxy,-cthyl)-2-acetoselenopheneq 11,11-di(earboxy-
a t I 1Y I)-1--propioselenophona, I-riiethyl-11-carboxy-
and 3-mothyl-11,11,11-tr'-
(SohoMo I . Tho
reduction of the 11-iiic~tliyl-lt-ayatio-ot)iyl-2-
propioselanophone with formic acid according to the
method by L.N.Kost and his collaborators (Ref 0)
the,3,3-dimethyl-2-(selenienyl)-piperidon-6 was
Card 2/3 synthenized (Scheme 2). In the synthesis of the

The ChoLiztry of SelenophOne. X111- Cyano-Ethylation, SO'V/79-20-11-30/55
of the Ketones of t.'lie 3eje.,jOp.,,jere Series
2-isobutyroselenophene, 3-methyl-2-isobutyroselenol)henc,,
and similar selenophenes it became evident that the
~;ilicio unhydridon of the saturatedm*wvalent or-.-.-.Iic
ac ids are convenient acylation a,~enta of tho selenophe:;O.
aucleus, which in also the case in the synthesi 's cf tile
Iletones with ramified radicals. There -are 12 references,
8 of which are Soviet.
ASSOCIATION: MoskovQl-iy gosudarstvennyy universiLet (moscow State Univer-
sity)
SUBMITTED: Septa-lber 20, 1957
Card 3/3

lv"M_4 #QP" t RNR &39 a rat=_
-----------
AUTHORS Yurlyev,--Yu. K.,-Ilezentsova, 1. 11. SOV/79-28-11-31/55
TITLE: Chomirtry of Solenop-hene (Khimiya selenafena) XIV.
Reac -tions of Selenophene-2-Aldehyde (XIV. I_eaktaii so-
lenofen-2-alldegida)
PERI ODICAL. Zhurnal obahchey khimii, 1958, Vol 26, Nr 11,
PP 3041 3045 (USSR)
ABSTRACT: Continuing earlier papers (Refs 1-3) tile nut'.',.ovL;
further investiC;at ed the reactions of sol. c)i~ o
aldebyde which are characteristic of armiaLic -J,,chydes.
They introduced this aldehyde into the Hantsch
(Ganch) reaction and in a condensation with acetic
ester and v:z-mi-a obtained the diethyl ester of the
dicarboxylic acid (Scheme*1). The condensation of
selenophene-2-aldehydes with barbituric acid, malonic,
acid and malononitrile yielded the selenenal-2-barbi.-
turic, selenonal-2-malonic acids, and selenenal-2-
malononitrile (Scheme 2). In the cleavage of the
Card 1/2 5-(f3elenenal-21~thiazolidone-4-thione-2 (Ref 2) with

Chemistry of Selenophene. XIV. Reactions of Seleno- SOV/79-26-11-31/55
phen e - 2 -Al d ehyd e
alkali liquor the 2-thione-3-(selanionyl-2l)-propionic:
acid was obtained in -,ood yield, which on the action
of hydroxylamine was transformed into the 2-oximino-3--
(selenienyl-2l)-propionic acid (Scheme 3). The oxime
of selenophene-2-aldehyde served as basic product for
the selenenyl-2-amine, obtained by the reduction of
nitrile. The condensation of this ,mine with
selenophene-2-aldehyde lead to the '.--I-(3elenenal-2')-
selenenyl-2-amine, with salicylic aldehyde to the
N-s--14C,rlal-(selenenyl-2l)-amine, which could form
_7 T'icr- nre 2 figures and
vcfo.rences.
ASSOC IAT101i Mo.- ."YY unlverOILOL (i-,~oscovi State
Univeroity)
PUBMITTED: September 30, 1957

Card 2/2

LUTHORSt N., SOY/79-28-12-22/41
TITLE. Tht-., Chemistry of Selenophane (Khimiya selenofena) XV. 2-Vinyl
Selenophene (Xv. 2-Vinilselenofen)
PERIODICAL: `Zhuxnal obahchey khimii, 1956 Vol,28, Nr 12, PP 3262-3265
ABSTRACT3 Contin'-,ing their 4a:!~ljer papera in the field of selenophene
,,hsiaistry with respoot to 14-he selenophene-a -aldehydes (Refs 1-5)
the alathors synthas~zed tho 2.,Yinyl selenophene; the
aatalytiQ dehydrai;ion of methyl-(selenienyl-2)-carbincl turned
out to be a better uynthesis -method than the decarbo-Tj,lation
of P -(.selenienyl)-2-aarylic acid, aa it led to the synthouis
of 2-pinyl selquophene in considerably higher yieldst
-4T C) cop
CTION CH3 CH-CH 2 1 1 OH_4H__CO0H
e
Met as well as the ethyl and
were obtained by the reaction
Card 1/3 of selenop'luene-2-aldehyde with alkyl and aryl magnesium halides.

The Obemistry of Selenophene.XV.2-Vinyl Selenophene SOV/79-28-12-22/41
In the investigation of the effect of various dehydration
agents on meth,,fl,-(selenieriyl-2)-oarbinoI it was found 'that in
the presence of acid nompounds (of potassium bisulfite, p-
toluene-sulfonic aoid etc.) as well as in the presence of
caustic potash the 2-vinyl selenophene.formed is almost com-
pletely polymerizel. In the thermal dehydration the yield of
thwa amount.$ to 50%~ whoreae in 8he dehydration in the vapor
phase with aluminum oxide at 200 thig figure is 60%. In the
aDove-mentioned decarboxylation reaction the yield amounts
to 40% only. 2-7iriyl selenophene reacts with diazo methane
and forma 44seleniany-0-21)-pyrazolinet and with dimethyl
formamide in the presence of Dhoophorus oxychloride the
(Si~hame 2). - In the oxidation of
the latter with silver oxide the P _(selenienyl-2)_aorylic
acid was obTained, with hydrogen peroxide, however, selenophene-
2-.qarboxylic acid (Scheme 3). There are I table and r, Soviet
referenoes.
ASSOCIATIM Moekovskiy gasudars-tvannyy universitet (Moscow State University)
Card 2/3

AMOits:
TITLE
SOV/51-fi-1-8/30
N.A., Xate-sk-,~,, V,M. and Yurlyeir,. YU-K,
Ti~,s ar,4 Raman 3-rfsqtra of Solon"spharzo and Its Mattjel
MRIODMA-L - OptIks i 3,)-3ktr-3z.,1ccPiya, 1150, Vol kz, Nr 1. pp 45-,qo (USSR)
ABSTRACT,
Card 1/3
'fas r-~roxti: L~f t;:vs Irarared and ultraviolA.,aboorption
!"Ve~:trr- An-- Aanai~ :-~p*.-~tra czfA,.)1ouc3:4,e3* ki),
(V", V1 ri
i . no ( a
Ra-man zre,~tra wera cbtainee- on a Stainhoil apectrograph (linear
di.:F-oarz4i,,r 0.1. =/11 The absorptica spectra In the infrared were
vbta-1-ar,' ar. !K-11 spactr=etor with LiF (3300-5000 CM 1).
and Or (400-00 CM-1) prism. An infrared
r-Poetrm%tor 770TIM-S 'with a NaCl prism vna also sased. The ultraviolet
woro cbtainal In lapoot%na uu&rr, rA- SP-4 spoctro-
rhott-mater. laeamirwmata of, tho Id rarad spectra, obtained usius the
V*(KM-3 cpactrzmate.-, an4 of the ultraviolet spectra were carried out
at the Optii~s Laboratory of of the Academy of Sciences of the
U.S.S.R. Salenopheae and its hi=ologaes atudied ia the prasent Work

.,the Absorption and Farnan Spectra of Salanophana and Its, Mathyl Hmologw
had the properties given in a table on p 50. Fig 1 gives the
Raman spectra of substances 1, 111 and V (curves a, 4 and C re3pectively).
Fig 2 gives the infrared absorption spectra of all t-he six substances
,studied and Fit 3 give; the corresponding ultraviolet absorption spuetr.&,
In all the substances (with the exception of VI) characteristic intense
1
absorption bands appeared in the infrared between 1209 and 1250 cm
The coincidence of certain frequencies and the general similarity of
the infrared absorption spectra of thiophene and selenophene and its
homologues, -aa be taken as confirmation of the plans structure of
sale.-ophave, Ydiich balcnKa tc the C2-F type of symmetry. i'he Raman and
the infrared absorption spectra of selenophana agree with the results
reported by Gording at al. (Raf 1). The spectra of selanophene
homolo&ues show characteristic frequencies due to vibrations of the
substituents (tabla on pp 4:6-4:7). The ultraviolet absorption spectra
ef selenophana and its homologues, obtained in the region 2200-2800 A did
not differ graiitly between each other (Fig 3). The ultraviolet spectre.
Cara 2/3 of thiophene and its homologuos behave in a similar manner The authors

SOV/51-6-1-8/30
'The Absorption and Raman Spectra of Selenephans and Its Kethyl H=Ologueg
suggest that the Infrared absorption and the Raman spectra of
seleacphane and Its homologues may be used for identification of
these compounds. There are 3 figures, 2 tables and 11 references,
5 of whicn are Soviet, 3 Frene--h, 2 English and 1 Japanese.
SUEOTTED; March 31, 1958
Carl 3/3

S/055j59/000/06/21/027
2004/BO02
AUTHORS: Yurlyev, Yu. K., Rozantsev, E. G.
TITLEs Dehydration of 2rM I-Trimethyl-3-oxyfuranidine~
PDRIODICAL: Vestnik Mookovskogo universitetal Seriya, matematiki, mekhaniki,
astronomii, fiziki, khimii, 1959, No. 6t pp. 171-179
itUt During the dehydration of 2,3,5-trimetbyl-3-oxyfuranidine by means of
,,p-toluene-sulfonid acido the three isomers shown in the scheme on p 171 may,
,develop, which differ from one another by the position of their double I)onds.
It was the purpose of this paper to isolate these isomers from the reaction
product. The starting substance was produced from 2,5-dimethyl-furanidcne-3
!'according to reference 3. By fractionating the product obtained from the
reaction with p-toluene-sulfonic acid, the authors obtained three main fractions
(Table 1, Fig. 1). From the first main fractiont 2,3,5-trimethyl-&3-dihydro-
furane was isolated. Its structure was shown by treatment with ozone (develop-
ment of ketonic acid) and by proving the methylketone group by means of KIO
V
furthermore by its Raman and infrared spectra (Table 2, Fig. 2), but mainly by
means of the infrared spectrum within.the range 2T40 - 3100 cm-1 (Fii;. 3). If
Card 1/3

Z
Dehydration of 2p3p5-Trimethyl-3~-oxyfuranidine 3/055/59/000/06/21//027
B004/BO02
clearly shows the absorption bands at 3065 am-1 of the CH groups of,!LN,3-di-
hydr,l)-furane. The ultraviolet spectrum (Fi& 4), however, has no absorption
maxitia, but it shows the absorption which corresponds to substituted ethyleae.
2,3,$-trimethyl-&-dihydro-furane was isolated from the third main fraction.
Its structure was determined by the oxidation with-ozone into-2-penten-one-4 and
the oxidation of the latter into crotonic acid by means of KBrO. Table 2 and-
-IL'igures 2,3,4 also give-the correspon ding spectra of these compounds. The 1
Raman spectrum shows-that the interise.line of the double bond is 1581 am- as is
--the -case -with - t e-similarly built cyclic vinylether. At 3095 am-' the infrared
spectrum shows the absorption bands of n, 2-dihydro-furanee The ultraviolet
-spectrum shows the conjugation of the double-bond-of the cycle with the free
electron pair of oxygen.-The third isomer, namely 2,5-dimethyl-3-methylene-
fUraniline was assumed in the second main fraation. After treatment with 2
2,4-diiaitro-phenyl-hydrazine for the purpose of separating 2*3P5-trinethyl-ZN_,-di-
hydro-furane, the.substance was again fractionated, and (Table 3) 2,M-tri-
2
i methyl-,~X -dihydro-furane was again obtained. Thus, the dimethyl-mothylene
compound is unstable and is rearranged into the two trimethyl compounds. Therel
are 4 figures, 3 tables, and 17 references, 5 of which are Soviet.
Card 2/3

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Card-3/3

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to
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car&

Alkylation of Benzene With T4traalkoxy Silanes SOV/79-.29-2-16/71
alkyl benzenea, On alkylating benzene with tetraalkox:f silanee
in the preserce of alumimm a-ad iron chloride the eame ieo-
merization takea pleoe of the alkyl. radical entering the I.-enzene
nucleug as is the case of the alkylation of alkyl halides all-
cording to G. Gustavson (Ref 7). The result,_:i obtainael in the
work un(ler re-.r4lew made it possible for the authors to suggast
the described scheme of benzene alky-lation with tetraalkoxy
silanes. Thu.5, manoalky'. benzenes were obtained withDtt im-
pur-ties ef dialkyl b-_nzensa. On alkylating naphthalenip, unde.-
the above tzons, al.,3o a hyl benzere (12%) was ob4 Jr-ed,
beeides a-ethyl naphthalene (29/.". There are I tab'-,-, and 8 ref-
erences, 4'of which are Soviet,
ASSOCIATION: Moskovskiy gosudarstyennyy universitet (.moacow State Unive--sity)
SUBMITTED: December 29, ';gr?
Card 2/2

SOV/79-29-2-.69/71
.,AUTHORS., Korobitsyna, 1. K., Fivaitskiy, K. K.p Yurlyev, Yu. K.
TITLE: 'Letter to the Editor (Pialmo v redaktsiyu)
Synthesis of Mono and Diketonas of the Tetrahydropyrane Series From
Furanidones--3 and furanidindiones-3-94 (Sintez-mono- i diketonov
ryada tetragidropirana iz furanidonov-3 i furanidindioaov-3.4)
PERIODICALt Zhurnal obahohey khimiip 1959, Vol 29, Nr 2, pp 6911-693 (IJSSR)
ABSTRACT: In continUatioA of their earlier works and basing on the experience
gathered concerning the synthesis and properties of the ketones of
the tetrahydrofuran series, the authors carried out the 'reaction of
diazomethane sol-fed in.ether (7.2 g, 21 % ezoess) with 20 g 2?295,5--
tetramethylfuranidone-3 in ether in the presence of methanol (at 200,
3 days) and obtained 3-95 g 2,2v6,6-tetramethjv1 tetrahyllropyzone-3
(18 % yield, calculated for the ketone introduced into the reaction,
boaidoa traces of 2,2,696-tetramethyl tetrahydroPYrone-,4 (Scheme !)
(Ref 2)~ On the action of diazomethane upon 2,295,5-tetraalkyl furani-
dindione-3,4, the 3-diketones forming with the extensi.= of the
cycle are methylated by diazomethane, vihich fact loads to the methyl
ethers of 2~2v5?5-tetraalkyl tetrahydropyrandiones,-3,ff- Thus~ fQr
Card 1/2 example, the methyl other of 21216y6-tetramethyl tetraJVdropyran:]iane-A5

SOY/79-29-2-69/71
Letter to the Editor. Synthesia of Mone and DIketones of the Tetrabydropyrane
Seriao From Faranidones-3 and Furanidinuionee-394
was .obtained on the action of diazomethane solved in ether upon
212,5,5-tetramethyl furanidindicno-314~ The hydrolysis of the
product with hydrochloric acid yielded 212,6~6-tctramethyj tetra-
hydropyrandione-3p5, which is soluble in alkali lye. The reaction
carried out according to scheme 2 ofo(-diketones with dia;,,omethane
is-deacribed by only one example in publicatl(zw, namely J,,l the cone
of camphor quinone (Ref 3).- There are 3 references, 2 of which are
Soviet. ~
ASSOCIATION: Moskovskiy gosudarstvennyy universitet
-(Moscow State University)
SUMITTEDs October 29, 1958
Card 2/2
(3) SOY/79-29-4-6/77
MHORS; yur,yev, yu. K., Dyatiovits,k Iayaj S-.-- V-
S-With
TITLE: Ethylene sulfide In the Synthouin of Heterocyclic COMPOUnd'
Two Hetero Atoms (Etilensulffid v sinteze geterotaikliotleskikh
coyeaineniy s dvumya geteroatomami). IX. synthesis of 2,-Acyl-3-
~aryl Thiazolidines (IX. Sintez 2-atsil-3-ariltiazoli4inov)
PERIODICAL.' Zhurnal obshchey k-himii, 195 .9t Vol 29., Nr 4, PP 1083-10.86 (USSR)
ABSTRACT: On the strength of their previous papers (Refs 1-5)-the authors
could expect that under certain conditions a-keto aldohydes with
N-(P-mercapto-ethYl)-aryl =ines would primarily react with
their aidehyde groupo and that in this way the synthesis of
thiazolidine ketoneS hitherto unknownv with one carbcnyl group
in position 21 would be possible (Ref 6). Methyl glyoxal and
phenyl glyoxal were introduced into the condensation with N-(P-
t"L c Yl-
and 2-banzo.
~me~rcapt~o-eth~~l) y amines, and several 2-acetyl
oli r were obtained in yields of 41-95%;
cancels - V - A-

SOV/79-29-4-6/'77
Ethylene Sulfide in the Synthesis of Heterocyclic Compounds With Two Hatero
Atoms. IX. Synthesis of 2-Acyl-3-aryl Thiazolidines
Ar-C6H5; o- and p-CH3C6H 4; o- and P-CH3 dc6R4; P-C2H500fic 6H 4;
R-CH 31 C6H5' The absorption spectra in the infrared range of
2-acyl-3-aryl thiazolidines synthesized in this way exhibited a
maximum which corresponds to the aboorption band of the carbonyl
group (Ref 7). The obtained ketones from 2-acyl-3-aryl thiazoli-
dines enter but very difficultly some reactions characteristic
of ketones. For instance, they do not react with seml.carbazide
or thiosemicarbazide, not even on prolonged heating :~Ref 8).
Oximes of these ketones cannot be obtained owing to a cleavage
of the thiazolidine ring observed in the experiments. There are
8 references, 6 of which-are Soviet.- I
ASSOCIATION: Moskovskiy gosudar8tvennyy universitet (Moscow State University)
SUBMITTED;' February 20, 1956
Card 2/2

-A
50)
AUTHORS:
TITLE:
PERIODICAL;
ABSTRACT.-
Card 1/3
SOV/79-29-4-9j'77
Yurlyev, Yu. K,, ZaytBeva, Ye. L.
... ................
Chemictry-of Selenophene (Khimiya selenofena). XVI. 4- and
5-11itroselenophene-2-aldehyde and the Synthesis of Isomeric
Mononitrouelenophenes (XVI- 4.- 1 5-Nitroselenofen-2-alldegid i
sintez izomernykh mononitroselenofenov)
Zhurnal obshchey khimiit 1959, Vol 29t Nr 4t PP 1067-1093 (USSR)
In connection with the previous paper (1) the authors decarboxy-
lated 5-nitroselonophene-2-carboxylic
in the quinoline medium in the presence of
pulverized copper, -and obtained e. y1eld of 59.5% pure 2-
nitroseleneo7.Lher,~iz.Nitroselenophene synthesized in this way melted
at 33.5-34u and differed from the preparation obtaimed by
S. Umezawa (Ref 3) by direct nitration of belenophene which
melted,at,45-460. As the repeated recrystallizatio.a of 2-nitro-
selenophene synthesized by the authors did not alter its melting
point and the elementary analysis pointed to this, they con-
cluded that the preparation of Umezawa. was a mixture of 2- and
3-nitroselenophene, and that this result could be supported by
investigation of the absorption spectra of isomeric mononitro-

Chemistry of Selenophene. XVI. 4- and 5-Mitroselenophene-2-aldehyde ;=d the
Synthesis of Isomeric Mononitroselenophenes
selenophenes obtained in different ways. The product described
by Umezawa thus represents, according 'to the investigations of
the authors, a mixture of 2-nitroselenophene (3041) and 3-nitro-
selenophene (70%). From the nitration of selenophene-2-aldehyde
with the nitration mixture a mixture results consisting of
4-nitroselenophene-2-aldehyde, 5-nitroselenophene-2-aldehyde,
and 2,4-dinitroselenophene. The first and the latter were sep-
arated therefrom. The presence of 5-nitroselenophenti-2-aldehyde
vas confirmed by the absorption spectrum in the ult:vaviolet
rango. The oxidation of 4-nitroselonophene-2-aldehyde and the
docarboxylation of tho resulting 4-nitroselenophene-2-carboxylic
acid lead to the formation of 3-nitroualonophone. 1he absorption
spectra in the ultraviolet range of the nitro derivativeo of
selenophene under invest-~gation are similar to the spectra of
the corresponding nitro derivatives of the furan- and thiophene
series, which is due-to the diene,structure of this compound
rather than to the nature of the hetero atom. There are
4 figures, 1 table, and 10 references, 2 of which are Soviet.
Card 2/3'

50)
ALMORS z
Yuryyev, Yh,&., Belyakova, Z* V.
SOV/79-29-5-11/75
TITLE: Tetraaoyl-oxy-silanes in Organic Synthesis (Tetraatsiloksisilany
v organioheskom sinteze).
20. Synthesis of fl-Diketones by Aoylation of Malonic and Acetcacetic
Eater With Tetraacyl-oxy-allanes (20. Sintez Adiketorov
atailirovard.yem malonovogo i atsetoukausnogo efirov
-tetraatsiloksisilanami)
PERIODICAL: Zhurnal obahchey khimiit 1.959, Vol 29, Nr 5,, pp 1458-1463 (USSR)
ABSTRACT: An interesting synthesis method of /Idl-ketones of tho ROOM 2COR
type is the acylation of malo-nic ester with acid anhydrides in the
presence of magnesium oxide or copper acetate catal3st (Ref 16).
In the present paper it was investigated whether silicides of
monobasio organic acids can be used in this reaction. By their
application to the acylatlon of mallonis., este.- in tha presence of
magnesium oxide or copper acetate at 165-170P the following
A-diketones were obtained in vields of 34-3'1%-- pentanedione-2,4,
hentanedione-3,5, non&ned.;o~ae-4,6, undecanedione-5,r, 2,6-dimethyl
nonanedione-4,6 and tridecanedione-a",,S. By the action of banzoic
Card 1/3 acid silioide on maloni*,ester dibenzoyl methane -gas obtained in a

Tetraacyl-q,xy-silanes in Organic Synthesis. SOV/79-29-5-11/75
20. Synthesis of O-Diketones by Acylation of Worjx and Acet-Oacetic Eater Ttith
Tetraacyl-o xy-e Llanes
method of synthesis for A-diketon,3s of the
19% yield. Furthe
Card 2/3
r a
CH COM?OOR type was devised. It consists of acylation of the
3
acetoacetic eater,with silicides of saturated monobasic organic
acids. The reaction takes place under the same conditLons and with
subsequeiit ketonic, cleavage of the obtained G-aoyl derivative of
,the acetcacetic eater. in this way the followingp-diketones were
obtained in yields of 34-5-77%: pentanedions-2,4v haxanedione-2,A,
heptanedione-2,4, 6-methyl-keptanedione-2,4 and nonarLedione-2,4.
The yields increase on a change of the ratio aoid: acetoacetic eater
from -1 -. 11 to 2 -. 1. in the synthesis of the /3-diketones of the
CH COCH2COR type by acylattion of the acetoacetic ester with
5
totraacyl-oxy-silanes it is noValways suitable to isolatte them in
the foxm of copper salts. On slow diotillation suffteiently pure-
#-diketones are obtained in good yields. The lo"s yields which are
obtained on separation on copper salt are probably due to the fact
that too little copper salts are formed from the A-diketone mixthwe
with corresponding asters. There are 23 reforenoes.

9-5-3.2175
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