SCIENTIFIC ABSTRACT MAKIN, S.H. - MAKINSKIY, T.A.

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• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

lu"Killy S. M.
"Estem of /,-Phenyl-4-?lper.`Ldolj ',!*:_t.,. FuncLic;nal -)'ubstJLtuto,, in
the Presence of Nitror?en and in Acyi. Groups." Canu Chev: 3ci,
Moscow inst of Fine Chenical Technolo~-,y Lmeni ". V. Lormonosov,
11 Oct 54. (VIII, 29 Sep 54)
SO: Sum 432, 29 XP-r 55

459
AUTHORS: Nazarov, I. N., and Wikin, S. M.
TIM: Heterocyclic Compounds, Part 50. Synthetic Anesthetics. Chap. 13.
Reaction of Primary Amines with beta, beta-dimethyldivinylketone
and 1-methoXY-5 methyl-4-hexene-3-on. Esters of 1,2,2-trimethyl-
4-phenyl-4-Piperidol (Geterotsiklicheskiye soyedineniya. 50.
Sinteticheskiye obexbolivayushchiye veshchestva. XIII. Deystviye
pervichnykh aminov na beta, beta-dimetildivinilketon 1 1 metokal-5
metil-4-geksen-3-on. Slozhnyye efiry 1,2,2-trimetil-4-fenil-4-
piperidola)
PERIODICAL: Zhurnal Obshchey Khimii, 1957, Vol. 27, No. 1, PP- 94-100 (U.S.S.R.)
ABSTRACT: A study of the reaction between primary amines (methylamirra,
ethylamine, isopropylamine) and 1-methoxy-5-methyl-4-hexene-3-on
taking place at room temperature showed only the addition of the
amines according to the double bonds and the formation of unstable
methoxyketoamines which during the distillation in vacuum decomposed
almost entirely into initial comporients. The reaction of 1-methoxy-
5-methyl-4-hexene-3-on with aquecus solutions of primary anines
(methylamine, isopropylamine) at 60-650 for 4-6 hrs resulted in
the formation of 1-21kyl-2,2-dimethyl-4-Piperidones. The reaction
Card 1/2 of methylamine though smoother than that with isopropylamine, showed

Heterocyclic Compounds, Part 50 459
considerable tar formation (resinification). Efforts to eliminate
tar formation by reducing the reaction temperature or by decreasing
the heating period produced no positive results because of the
formation of almost inseparable mixtures of piperidones and iso-
meric amines. Cyclization into gamma-piperidones during the
reaction of primary amines with beta-beta-dimethyldivinylketone
is less smooth but with much smaller yields than in the case of
other divinylketones having substitutes in both vinyl groups.
The reaction of 1,2,2-trimethyl-4-piperidon with phenyl lithium
yielded about 60% of 1,2,2-trimethyl-4-phenyl-4-piperidole the
esters of which were obtained for pharmacological experiments.
ASSOCIATION: Moscow Institute of
(Moskovski Institut
EomonosoZ
PRL9ENTED BY-
Fine Chemical Technology im. M. V. Lomonosov
Tonkoy Khimicheskoy Tekhnologii im. M. V.
SUBMITTED: November 9, 1955
AVAILABIE:
Card 2/2

Al -
460
AUTHORS-. Nazarov, I. N.; Makin, S. M.; and Grapov, A. F.
TITLE: Heterocyclic Compounds. Part 51. Synthetic Anesthetics. Chap. 14.
Esters of 1,2,5-trimethyl-4-phenyl-4-Piperidole with Functional
Groups at Acyl radical. Analogues of promedol and Isopromedol. 1.
(Geterotsiklicheskiye Soyedineniya 51. Sinteticheskiye obezboli-
vayushchiye veshchestva. XIV. Slozhniye efiry 1,2,5-crimetil-4-
fenil-4-piperidola s funktsionallnymi gruppami pri atsillnom
ostatke. Analogi promedola i izopromedola. 1)
PERIODICAL: Zhurnal Obshchey Khimii, 1957, Vol. 27, No. 1, pp. 101-1-10 (U.S.S.R.)
ABSTRACT: Studying the physiological activities of various esters, the authors
synthesized numerous 1,2,5-trimethyl-4-phenyl-4-piperidole esters
containing (in the acyl radical) alkoxy, phenoxy and alkylsulfide
groups as well as halides, nitrogen and double bonds. It was found
that the introduction of these groups into the acyl radical of
acetic and propionic esters of 1,2,5-trimethyl-4-phenyl-4-piperidole
sharply reduces or completely destroys the analgetic activity of
these substances. Esterification of 1,2.5-trimethyl-4-pherql-4-
piperidole with chlorides of analogous acids by the Spasov (4)
Card 1/2 method led to the formation of methoxyacetate and ethoxyacetate.

Heterocyclic Compounds. Part 51. 460
Esterification with chloride of beta-phenoxypropionic acid gave
beta-phenoxypropionic ester. Results showed that, of the many
esters synthesized, only acrylate and methacrylate showed a
considerable anesthetic effect equal to 35-50'p" of the promedole
effect, all other esters were practically void of any morphine-
like activity. Propionates were found to have maximum analgetic
activity of all the 4-phenyl-4-piperidole esters investigated.
There are 14 references, of which 4 are Slavic.
ASWGIATION.- Moscow Institute of
(Moskovski Institut
LamonosovaT
PRESENTED BY:
Fine Chemical Technology im. K. V. Lomonosov
Tonkoy Khimicheskoy Tekhnologii im. H. V.
SUBNITTED: November 9, 1955
AVAILABLE:
Card 2/2

,AUTHORS: Nazarov, 1. N. and Makin, S. M. 79-2-50/58
TITLE: Heterocyclic Compounds. Part 52. Synthesis of 1-gamma-.klkoxypropyl-4-
Piperidones and 1-gamma-Dialkylaminopropyl-4-Piperidones (retero*tsik-
licheskiye soyedineniya. 52. Sintez 1-ga=a-aikoksipropil-4-piperidonov
i 1-ga=a-dialkilaminopropil-4-piperidonov).
PERIODICAL: Zhurnal Obshchey Khimli, 1957, vol. 27, No 2, pp. 499-509 (U.S.S.R.)
ABSTRACT: Considering the great importance of gamma-piperidones for the synthesis of
now physiologically active ccmpounds possessing strong pain killing,
anesthetic and spasmolytic properties, the authors investigated the re-
action between vinylpropenyl ketones with gamma-dialkylaminopropylamines,
gamma-alkoxypropylamines 'and gamma-ethylmercaptopropylamine which are
easily obtainable from acrylonitrile. It was found that different vinyl-
propenyl ketones react with the above amines much easier than with or-
dinary alkyl amines, giving high yields of gamma-piperidones. Instead
of vinylpropenyl ketones, it is quite possible to utilize homologous
beta-methoxy ketones which form as a result of addition of methanol to the
Card 1/2 vinylpropenyl ketones. The outhors synthesized more than tweniy now gamma-

Heterocyclic Compounds. Part 52. 79-2-50/58
piperidones and 2-methyl-4-ketodecahydroquinolines of three different
types.
Some of the gamma-piperidones derived were reduced with the aid of by-
drazinehydrate by employing the N. M. Kizhner method (10), into hamo-
logous piperidine bases.
There are 11 references, rf which 8 are Slavic
ASSOCIATION: Moscow Institute of Fine aemical Technology Imeni M. V. Lomonosov
PRESENTED BlYt
SUBMITTED: Novembe-c- 9, 1955
AVAIIABTE: Library of Congress
Card 2/2

OOTHORSi Nazarov, I. N. and Makin, S. M. 79-2-51/58
TITLE: Heterocyclic Compounds. Part 53. Synthetic Anesthetics. Chapt. 15.
Synthesis of 2,5-Dimethyl-4-Phenyl-4-Piperidoles and Their Esters Con-
taining, in Presence of Witrogen, Piamma-Substitutpd Propyl Radicals.
Analogues of Pranedol and Isopromedol TT. (Geterotsiklicheskiye soyedineniya.
53. Sinteticheskiye obezboli,~ayushchiye veshchestva. XV. Sintez 2,5-dimetil-
4-fenil-4-piperidnlov i ikb slozhnykh efirov snderzhashcbi-kh pri azote
gamma-zameshchennyye Propillnyyeradikaly. Analogi promedola, i izopromedola.
PERIODICAL: Zhurnal Obshebey Khimii, 1957, vol 27, No 2, pp. 510-518 (U.S.S.R.)
ABSTRACT: Some of the gamna-piperidones described in report 53 were used for the sim-
thesis of 4-phenYl-4-piperidoles Pnd their esters (acetates and propionates)
which belong to the group of hig)-ly actibe anesthetics. Synthesized were
numerous 1-propyl-2,5-dimethyl-4-phenyl-4-piperidoles and their esters
having in the DroDyl radical at the nitrogen (in game position) alkoxy,
alkylsufide and dialkylamine groups. The pripionates of 1-~Lgama-methoxy)-
Card 1/2 and 1-(gAmma-ethoxy)-propyl-2,5-dimethyl-4-pheny'L-4-piperidoles were found

79-2-51/58
Neterocyclic Compounds. Part 53. Synthetic Azesthetics. CYapt. 15.
Syntbesis of 2,5-Dimethyl-4-Phenyl-4-Piperidoles and Their Esters Con-
taining, in Presence of Nitrogen, Gamma-Substituted Proryl Rndicels.
An8logues of Promedol and Isopromedol II.
to have a high anesthetic (analgetic) and locally-anesthetic characteric-
tic. The snalgetic activity of all the esters described was still much
lower than the activity of promedol and Isopromedol. It was established
that a methyl. radical in presence of nitrogen, as comrered with other
known siibstitutes, has a much greater effect on the analgetic properties
Card 2/2 of 4-phenyl-4-piperidole esters.
There are 4 rererences, of whieb 2 are Slavic
ASSOCTATTON- Moscow Institute of Fine Chemical Technology imeni M. V. Lcmonosov
PRESFNTED BYi
STTEKNTED-. November 9, 19r,5
AVATLABLEi Library of Congress

20-114-3-28/60
AUMORS: NaZarqv, 1. N., Member of the AS us,9R, Krasnoya, Zh. A.,
Makin, S. M.
TITLE: AniOnOtrOPic Regrouping of 2,6-Dimetbvlocta~2x4p7-Triene-6-oI
(Anionotropnaya peregruppirovka 2,6-dimetilokta-2,4,7-triyes-
6-ola)
PERIODIM: Doklady Akademii Nauk SSSR, 1957, Vol 114,Hr 3, PP 553-556(Wsft)
I nam ly
ABSTP.40T. Polyene alcohols have an interesting characteristic,
that they are easily subject to anionotropic regrouping unfle
the influence of deluted acids, on which occasion hydroxyl
is shifted and the m=ber of conjugated double bonds is
increased. The investigation of this regrouping is interesting
from the point of view of the production of primary polyene
alcbhols, especially of those of an isoprenoidal type. The
authors investigated the anionotropic regrouping of the sub-
stance mentioned in the title, which, as regards the structure or
the carbon chain, is similar to linalool ILnalcool with an addl-
t1onal double bond. By the influence or lithium acetylide in a
solution of liquid amonia of 2-methyl-bepta-2,, 4-diene-6-on the
Card 1/3 hitherto not described 2,6-dimetbylocta-2,4-diebe-T-In-6-o1

Anionotropic RegrmVing of 2,6-Dimethylocta-2.,4,,T-Triene-6-01
20-1.14-3-28/60
was produced with a higt output. By absorbing 1 mol. of hydro-
gen in the presence of the Pd-catalyzer carbinol was changed
into 2,6-dimeth-ylocta~2,4,7-triene-6-ol. It is a liquid with
the pleasant well of flowers. There are two possibilities
for the anionotropic regrouping of caebinol. III: either by
the formation of a primary alcohol (dehydrogeraniol IV) with
the shifting of a double bond, or by the formation of a tertiary
alcohol with a parallel shifting of 2 double bonds. The authors
stated that only a tertiary alcohol V and no primary alcohol IV
develop on the occasion of a 1.5-hour-long iction of 0.05 %
sulfuric acid on carbinol 13:1. In order to prove this di-
rection of reaction the obtained alcohol V was subjected on
complete hydration. Then 2,6-dimethyioctane-2-ol(VI)de"loped.
The same alcohol VI was obtained by 't owing reactions -
2,6-dimethylocta-2,4-dierie-7-In-2-o:IL,=ch an aniono-
tropic regrouping is posdible oniy in the direction of the
formation of a tertiary alcohol, isomerizes under the in-
fluence of 1 % sulfuric acid i-arto 2,6-dimethylocta-3,5-diene-
7-In-2-*l M. This again changes under partial b~dration in the
presence of Pd-catalyzers into Vp and in the case of a complete
Card 2/3 hydration into VI. The saturated alcohols VI, obtained by eltber

20-114 3-28/60
Anionotropic Regrouping of 2,6-Dimethylocta-2,4,7-'-;riene-6-oI
of the above methods, produce 3,5-dinitrobenzoates (mole-
cular compoundgwith OL6naphthylamine)., which melt at the same
temperatur- (100 - 101 )'Q which. is unchanged by Joint melting.
The methylhoptidienonQ 1, ne-
cessary for the synthesis of carbinol II, was obtained by
two differert ways. 1) By pirolysis of the acetoa(Aate of
dimethylethynyle,-rbinol and 2) by the condensation of di-
meth,ylacryl-aldehyde with acetone under the influence of iSo-
propylate and of tertiary aluminum-amylate as well as of so-
dium hydrate (production 47,5 %). The experimental part with
constants, nethods, and production of the stibatances A!49-
cussed follows. - 2here are 4 references, I of which io Soviet..
ASSOCIATIONs Moscow Institqte for Fine Chemical Technology imeni M. V.
Lomonosov ('Joskovskiy institut tonkoy khimicheskoy tekhnologii
im. M. V. Lomoncsova)
SUBMITTED3 January 9, 1957
Card 3/3

AIJTHORSt Nazarov, I. N. Member, Academy of Sciences, 2o-114-4-32/63
USSR, Guser, B. F., Makin S, M., Mochalin, V. B., Hazarova,
I.J., Vinogradoy, V. P., Kruptsov, B. K., Shayrygina, 0. A.,
Nazarova, D. V.
TITLEt The Condensation of Acetylene With Methylheptanone and Its
Analogues (Kondensatsiya ateetilena a metilgeptanonom i yego
analogami) The Synthesis of Linalool and Its Analogues (Sintez
linalools i yego analogov) .
PERIODICkLi Doklady Akadem.ii Nauk SSSR; 1957, Vol. 114, Nr 49 pp, 796-799
(USSR)
ABSTRLCTt Several years ago a simple method of synthesis of different
acetylene alcohols was worked out in the laboratory of the
authors by means of condensation of aldehydes and ketones un-
der the influence of powdery caustic potash with acetylene at
high pressure (5-1o at superpreseure). It was of interest to
employ this method in the condensation of acetylene with methy)-
heptanone and similarketones, in order to obtain the correspond-
ing acetylenealoohols. Linalool and some gnalogues may then be
obtained easily by partial hydrogenation with a Pd-catalyst.
Hitherto such condensations have usually been carried out under
Card 1/4 the influence of metallic sodium in a solution of liquid ammonia.

The Condensation of Acetylene With Methylheptanone and Its 2o-1-14-4-32/63
Analogues. The Synthesis of Linalool and Ito Analogues
It was found that methylhoptanone and its various and1oguee
may be condensed very easily with caustic potash and acetyl-
ene at the above-mentioned pressure. At o-2oOC they give as a
result the corresponding tertiary acetylene alcohols with an
almost quantitative yield (more than go%*). This reaction may
also be carried out without acetylene pressure, however, some-
what more slowly and with a yield of only 6o-8o%. It has been
previously shown in the same laboratory that acetylene alco-
hols which contain a non-substituted acetylenehydrogen may be
hydrated highly selectively in the presence of palladium over
calcium carbonate or copper coated zinc powder. Thereby
,rin,Tialcohols with an almost theoretical yield are obtained.
The acetylene alcohols mV not be selectively hyLdrated with
other catalysts (Ni, Pt) and are therefore usfiless in the pro-
duotion of pure vinyl alcohols. An analoguas picture may also
be noticed with the hydrogenation of the above-described aoe-
tylene alcohols which are obtained by condensation of acety-
lene with methylheptanone and its analogues. These acetylene
alcohols may also be highly selectively hydrated in the pre-
Card 2/4 sence of a Pd-catalyst. They form linalool and its analogues

The Condensation of Acetylene With Methylheptanone and Its 2ck -3-14-4-32/63
Analogues. The Synthesis of Linalool and Its Analogues
with an almost theoretical yield. The purity control of the
vin.Tlalcohole (linalool and its analogues) was carried out
by means of the acetylene test (with ammonia solution of
silver or copper oxide), whose aensitiveness was det3rmined
by special teats and amounted to 0,2-0,3%. At the hydrogena-
tion of the acetylene alcohols with a Pd-oatalyst the aoety-
lene test always disappears at the theoretical point, that is,
as only one hydrogen molecule is strongly attached. The acety-
lene alcohols obtained in the course of this work are summa-
rized in table 1. Linalool and its analogues (table 2) were
obtained by a partial hydrogenation of the above-mentioned
acetylene alcohols with Pd-catqlyats. In the experimental part
the methods and yields of the said substances are described in
detail. There are 2 tables and 5 references, 3 of which are
Soviet.
ASSOCIATIONs Institute for Orffanic Chemistry imeni N.D. Zelinakiy of the AN
'USSR and Moscow Institute for Refined Chemical Technology imeni
M.V. Lomonosov (Institut organicheskoy khimii im. N.D. Zelins-
Card 3/4 kogo Akademii nauk SSSR i Moskovskiy inatitut tonkoy khimiches-

The Condensation of Acetylene With Methylheptanone and Its ,I.- 114-4-32/63
Analogues. The Synthesis of Linalool and Its Analogues
koy tekhnologii im. M.V. Lomonosova)
SUBMITTEDs March 12, 1957
Card 4/4

IN, j - 14f. 20-5-31/60
AUTHOR NAZAROV I.N., member of the Acadeayv low
3.P., 1=19,S.M. azA
YA5OV3iFYi,L.A., GUSIV)
NIZAR071;1.1.
TITLE The Synthesis of Geranjlacetone, 3-Methylgaranylacatone,
Poeudolonon and Peaudotron.
(Sintez geranilataetonao 3-meiiigerafilataetor-',
PGeT1-.'A,)nOna i pseydoirona.- huaalsal
PERTODIOAL Doklady Akademy Nauk SSSR 1957, Vol 114 Hr 5,
PP 1029-1032 (U.S.S.R.)
ABSTRACT In the course of systematic work on ths syntheeia of
iaopronoidoompounds a paper by Carrol attra,Aed the
attention of the author. That author reports that with
the heating of linalool with acetoacrtic etter, in the
presence of a small amount of sodium alcoholate, gerany-
lacetone with a 40-45 % yield develops. Kimel and Cope
obtained 61 % linalylacetoacetate from interaction of
Iftnalool with diketone, in the presence of m9tallic
sodium. Its pyrolysis at 170-235 0 lielded 76 % gerany-
lacetone. The authors thoroughly examined both syntbesis
varieties on linalool and 3-methyllinalool, in order to
work out a production method for geranylacetone and
3-methylgeranylacetone. It was found out thht reaction
proc"ds beet at 160-ISOOC without any catalysts.
CARD 1/4

20-5-31/6o
The Synthesis of Goranylaoetone, 3-Mothylgoranylacotons,
Pseudtouon and Pseudoiron.
90-95% of the theoretical 00 2-amount precipitato, and
an almost theoretical amount of aloonol (with admixture
Of aaetono) ia distilled. Sinae the latt-3r pr3ofsBS is
torminated oonaidertably oarlier t1ita t~f, 00 2-olimina-
tion, it may be assumed that the reaotien paoses the
seetoacetete-stage. A system is giTen. This meo'hariam.
was pro-fed by the authors for the re&otlon Ietweaja
dimethylvinyloarbinol and acatoaoatic other. From a
study of the second variety of synthesis the authors
found that the acylation of linalool and mathylinalool
with cliketone may beat be performed in the preagnce of
pyridine or triethylamine, and not of metallic sodium.
Based upon the results obtained, the authors decided
to inwestigate both varieties in dehydrolinalool and
3-methyl dehydrolinalool, in order to w6rk out synthesis
methods for poeudooionon and poeudoiron. Soxetime during
the beginning of this work a paper by Lacey was
published demonstrating the possibility of a synthesis
of dienones on most simple othinylearbinols according
to a general system mentioned here. The second half of the
reaction the pyrolysis of acetoacetate, was performed by
Lacey in the presence of small amounts of p-toluolaulfonic
CAD 2/4 acid. This kind of dienone synthesis was thoroughly

20-5-31/69
The Synthesis of Geranylacetone, 3-Methylgeranylacatone,
Pseudoionon and Pseudoiron.
studied in the laboratory of the authors. During the work
the pape.- by Haves of the same topic was published. He
also described a production method for 3-methylpseudoiron
from 3-methyldehy4rolinalool and a-methyl acetoacetio
ether. Recently Preobrashenskiy and collaborators wrote
on this topic. The authors studied b6th synthesis varieties
and found that the reaction between dehydr6linalool or
3-methyl dehydrolinalool and soetcacetic ether proceeds
beat at 110-180 0Co The yield of pseudoionon and pseudoiron
amounts to about 55 %. The aoylation of dehydrolinalool or
3-MethyldehydrolinAlool by diketone proceeds beat in the
p:eesence of pyridine or triethylamins. The pyrolysis of
the two mentioned slOstances thus obtained was performed
at 185-1950 C. In this connection about 80 % of the
theoretical 00 -amdunt.is obtained. The yield of pseudo-
ionon and pseugoiron amounted to 50-55 %, of the initial
materials. The oyolization of'the thus obtained pseudionon
CARU 5/4 with a mixture of sulfur- and ioe-aoetic acid gave*ionon

20-!-;-31/60
The Synthesis of Geranylacetone, 3-Methylgeranylacetone,
Poeudoioqon and Fseudoiron.
with a 65 % yield. Experimental part with the usual data.
(2 Slavic-referenoes)
A380CIATION: "N,D. ZELZINSKY" Institute for organic chemistry of the
Academy of Scienoesof the U-SSR.
(Institut organioheakoy khimii im.N.D. Zelinakogo Akademii'
nauk SSSR)
PRESENTED BY: -
SUBUTTED: 74-57
AVAITABLE: Library of Congress.
CARD 4/4

AUTHORS: Nazarov, 1. N., Academician, Makin, S. -M., 20-114-6-29/54
-
-
-
a
r
dov, V. P.9
Mochalin, V. B., Nazarova, D. V., Vinog
Kruptsov, B. K., Namrova I. I. and Shavrygina, 0. A.
TITLE: The Synthesis of Methylheptenone and Methylheptadienone
Analogues (Sintez analogov metilgeptenona i metilgeptadiyenona)
PERIODICAL: Doklady AN SSSR, 1957, Vol. 114, Nr 6, pp. 1242-1245 (USSR)
ABSTRACT: This synthesis is of interest for the production of a
number of corresponding analogues of natural isoprenoid
compounds. The initial acetylene-alcohols for this purpose
were produced according to the authors' method (reference 1).
By a selective hydrogenation in the presence of palladium
on calcium-carbonate acetylene alcohols are almost
quantitatively converted to analogous vinyl alcohols
(reference 2). These latter yield the corresponding
analogues of methylheptenone in three different ways
(reference 3). Method A. By the influence of gaseous
hydrogen chloride 8r hydrogen bromide upon tertiary vinyl
alcohols at 0 - 20 C primary haloid-derivatives of an allyl-
-type easily form (reference 4). Their condensation with
Card 1/3 sodium-acetate-acetic-ether with a subsequent saponification

The Synthesis of Methylheptenone and Methylheptadienone 20-114-6-29/54
Analogues
leads to methylheptezione analogues. Method B. At 140 -
19ooC tertiary vinyl alcohols directly react with the same
ether. An almost theoretical quantity of ethanol and CO 2 is
separated and the same analogues as in A) are obtained.
Method V. By the action of diketene upon tertiary vinyl
alcohols in the presence of small amounts of triethylamine
or piperidine, acetonacetic ethers of these alcohols are
obtained (table 2). Their pyrolysis also leads to the above-
-mentioned analogues (reference 6). The 2,3-dimethyl-2-
-heptene-6-on (IV) necessary for the synthesis of irone was
produced all three ways mentioned. Dimethylisopropenyl-
carbinal (initial substance) was produced by the influence
of methyl-lithium upon methyl-metacrylate. All methyl-
heptenone analogues produced are comprised in table 1. The
authors further produced: allyl- (1) (reference 9), crotyl-
(II) and oblorocrotyl-acetone (III) (reference 8), dimethyl-
isopropenyl-carbinol-acetoacetate, dimethylheptenone (IV),
cyclohexylidenpentanone (IX) and tertiary butylheptadienone
(XIII). The production methods and constants of these
substances are given. There are 2 tables and 12 references,
Card ?/3 6 o. which are Slavic.

The Synthesia of Methylheptenone and Methylheptadienone 20-114,6-29/54
Analogues
ASSOCIATION: Institute of Organic Chemistry AN USSR imeni N. D. ZelinBkiy
AS USSR and Institute for Fine-Chemical Technology imeni
M. V. Lomonosev, Moucow (Inatitut organichookoy khimii im.
N. D. Zelinskogo Akademii nauk SSSR i ,Ioskovskiy institut
tonkoy khimicheskoy tekhnologii im. M. V. Lomonoscova)
SUBMITTED: March 12, 1957
Card 3/3

AUTHORS: Nazarov, 1. N., Member of the Academy, 20-117 -5- 27/54
(Deceased), Dlaki~.S.__M.j and Kruptsov, B. K.
TITLE: The Synthesis of Ethoxyisoprene (Sintez etoksiizoprena).
PERIODICAL: Doklady All SSSR, 1957, Vol. 117, Nr 5, pp. 823-625 (USSR)
ABSTROT: The alkoxydienes are interesting for the organic chemistry by
the presence of 2 double conjugated formations since they can
be used furthermore for the synthesis of various substances
in consequence of a alkoxyl group capable of reac+4on.
Especially intersting is the ethoxy-isoprene (1-ethoxy-3-
mothyl-butadiene-1,3) since it can be used for the synthesis
of important isoprenoids (zitral, vitamin A, aarrotine and
others). It has a methyl-branching in the third position and
has therefore an isoprenoid structure. Reactions (I) - (IV)
are given by means of which the authors have obtained the
synthesis mentioned in the title. By action of tetra-
ethoxysilane on acetone the acetone-diethyl-ketal (II) was
obtained- The syntheses according to former references
(reference 1) led to only small yields (10-1500. The authors
obtained yields of 92% of acetone-ketal (in presence of
0,5 mol ethanol pro I mol tetra-ethoxysilane) by the
Card 1/3 anplication of phosphorous acid of 85 % as catalyst. Acetone-

The Synthesis of Ethoxyisoprene
20-117-5-2,7154
diethylketal was then introduced into the condeneation
reaction with vinyl-ethyl-ether. The addition of ketals
to these ethers was hitherto scarcely researched. The
authors succeeded in carrying out this reaction at 00 and in
presence of catalytic quantities of I.ri-fluorboron-othyrate
with a yield of 85% of 3-methYl-1, 1p3 triethoxybutane, with
reference to the acetone-diethylketal which enterel into the
reaction. In order to prevent a further condensation a ketal
excess has to be used which is higher by 1,5 times- In the
case of passage of vapors of the 1,10-triethoxy-3-methylbutane
by MgHPO4-catalyst at 3500 in a 15-20 mm-vacuum 2 alcohol
molecules are oplitted off and ethoxyisoprene is formed with
a yield of 77%- Furthermore this latter substance was obtained
with a good yield in the passage of vapors of the P-methyl-
croton-aldehyde-diethylacetal over the contact catalyst
NaH2PO . The initial substance in question was produced from
iso-vaterian-aldehyde (reference 6). In the experimental part
the usual data are given with the preparation of the catalyst.
Card 2/3

AUTHORS: Nazarov, I. N.(Deceased),,Mokin S. Y., SOV/79-29-1-25/74
Kruptsov, B. K., "fironov, V. A.
TITLE: Synthesis of Acetals and Ketals by Means of Tetraalkoxy-
Silanes (Sintez atsetaley i ketnley s pomoshchly-u tetraalkoksi-
silanov)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 1, pp 106-111 (USSR)
ABSTRACT: It is known that the most suitahle acetylnting agents Pre the
esters of the ortho-formic acid. Owing to their hi7h costs
they can however not be used as initial substnnce for the
synthesis of ecetals. As n substitute for th,2 above esters
the authors chose the :~nsily available esters of the ortho-
-silicic acid (tetraalkoxy-silanns). Relferich and Hansen
(Ref 1) found that the tetr8alkoxy-silpnes are nble to
acetylate aldehydes and ketones in n1coholic medium in the
presence of hydrogen chloride. The Puthors met however with
many difficulties at the attempt to obtPin some acetals and
ketals according to this method end the yields were Plso small.
For this reason, they investig.-ted thoroughly the reaction of
the tetranlkoxy-3ilnnes with nldehydes and ketones under diffei
Card 1/3 ent conditions. On the reaction of acetone with

Synthesis of Acetals and Ketals by Means of SOV/79-29-1-25/74
Tetraalkoxy-Silanes
tetraalkoxy-silane they used HC1, concentrated H 2s0 41
p-toluenesulfonic acid, phosphoric acid, etc. as catalysts for
the acetylation. Phosphoric acid proved to be the most suitable
catalyst. In contrast with the general opinion, tetrnnlkoxy-
-silanes react well with aldehydes and ketones in the presence
of some alcohol. Thus the diethyl ketpl of acetone with
tetraethoxy-silane was obtained in 93 16 yield, on addition of
0.5 % alcohol only. Many other acetals of various aldehydes,
ketones, etc. were synthesized n1so with good yields and very
limited use of alcohol. The small alcohol quentity is important
in the synthesis of low-boiling Rcetnls and ketels: It is thus
possible to obtain in the distillation the acetsl and ketsl
with minute alcohol quantities which can easily be removed by
water, which is rather difficult at higher quantities of Plco-
hol. In the synthesis of high-boiling acetals the amount of
the easily asparable alcohol is of no importance. in the
acetylation of the croton Pldehyde the alcohol quantity is of
particular importance: At 0.1-0.2 mol alcohol with I mol nlde-
Card 2/3 hyde dimethyl and diethyl Rcetal were resulting in a yield

Synthesis of Acetals, and metals by Means of SOV/79-29-1-25/74
Tetraalkoxy-Silanes
up to so %. On addition of more than 1 mol alcohol
1,1,3-trialkoxy-butanes sre formed as main products (Ref 2).
Without any alcohol the reaction yields 47 % only. For the
removal of the acetals and ketals two methods were anDlied
according to whether they are lower or higher boiling than the
tetraalkoxy-silanes used in the renction (see experimentni
part). The diethyl acetals of the croton nldehyde and methyl
heptenone were obtnined in good.yield by the eaters of
ortho-formic acid as well. Both tables present Pll scetals and
ketals synthesized. There are 2 tables and 3 references, I of
which is Soviet.
ASSOCIATION: Moskovskiy institut tonkoy khimicheskoy tekhnologii (Moscow
Institute of Fine Chemicnl Technology)
SUBMITTED: July 19, 1957
Card 3/3

OTHORS: Nazarov, I. 14.(Deceased), 90V/79-29-1-26/74
Makin, S. 111. , Kruptsov, q. K. , Mironov, V. A.
TITLE: Synthesis of Vinyl and Diane Ethers (Sintez prostykh vinilo-
vykh i diyenovykh efirov)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 1, Pp 111-117 (USSR)
A13STRACT: n the passage of the vapors of dimethyl and diethyl acetals
of the acetone of acetic acid, propi one, butyric Acid, iso-
butyric acid, as well as of the dimethyl An~ diethyl ketals
of acetone And cyclohexanone over 9aH 2POI and MgHPO4 (as enta-
lysts) at 300-3750 the nuthors obtained the substituted vinyl
ethers listed in t-ble 1. The simple diene ethers are consider-
ably interesting in organic chemistry since they possess two
conjuF,ated double bonds and a reqctive alkoxy 4roup. Further-
more,methoxy and ethoxy isoprenes were synthesized And the
methoxy and ethoxy butadienes previously described (Refs 7,8,9)
were investignted. The alkoxy dienes specified were_, obtnined by
catalytic cleavage of the acetals of croton Ani /3-methyl-
-croton aldehyde,as well as of the 1,10-trialkoxy-butanes and
Card 1/3 1,1,3-trialkoxy-3-methyl butanes. The dimethyl And diethyl

Synthesis of Vinyl and Diene Ethers SOV/79-29-1-26/74
scetals of A - mathyl-croton aldehyde were synthesized according
to scheme 1 in the presence of small quantity of BF 3.0(C2 H5)2v
the butpnes mentioned Pccordinir to reference 7 and scheme 2
(Refs 11,14915;16), The catalytic cleavage of the acetals of
croton and /-S-methyl-croton aldehyde, as well as of the
trinlkoxy-butanes into the simple dieno ethers was thus
carried out on thri catalysts NsE 2 PO4 and MgHPO 4* Active
charcoal, silica gel, and glass were used as cnrriers, This
process proceeded in vacuum 10-20 mm in the nitrogen current
(Scheme 3). The maximum yield of ethoxy-isoprone was attained
on the catalysts hIgHPO 4 on active charcoal and 1.*HPO 4' NaSiO3
(TPble 2). As to durnbility, rAgHP0 4 on charcoal proved to be
-4he best cAtalyst. The activity of the cataly!,ts produced from
NaH2PO4 decreases more rapidly. On the catalytic cleavage of
the 3-methyl-1,3-dimethoxy-l-ethoxy-butane a mixture from
methoxy- Pnd ethoxy-isoprene resulted in about the same
quantity. There are 2 tables and 16 references, 8 of which
are Soviet.
Card 2/3

. Synthesis of Vinyl and Diene Ethers SOV/79-29-1-26/74
I ASSOCIATION: Moskovskiy institut tonkoy khimicheskoy tekhnolol-ii- (',Ioscow
Institute of Fine Chemical Technology)
SUBMITTED: September 10, 1957
Card 3/3

5 (3) SOV/79-29-3-4/61
AUTHORS: Nazarov, 1. ff. (Deceased), [in .3. M., Mochalin, V. B.,
Shavrygina . 0. A., Nazarova, D. V., Kruptsov, B. K.
TITLE: Synthesis of Analogues of Geranyl Acetone and Pseudoionone
(Sintez analogov geranilatsetona i psevdoionona)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 3, pp 744-753 (USSR)
ABSTRACT: These analogues are inilial products for the synthesis of
the corresponding analogues of the most important natural
isoprenoid compounds, of vitamin A, carotene, farnesol, as
well as of phytol, a component of vitamins K and E. Recently,
the authors reported on three syntheses of ketones of the
isoprenoid type carried out by them: 1) By reaction of sodium
acetoacetic ester with halogen derivatives of the ally! type
(method A). 2) By reaction of vinyl- and ethynyl carbinols
with acetoacetic ester (method B), 3) By pyrolysis of the
acetoacetates of vinyl- and ethynyl carbinols (method V).
This method was used to obtain mathyl heptenone, methyl
heptadienone and their analoguen (Refs 1, 2). By condensation
of methyl heptenone and its analogues with acetylene under
pressure (5-10 atmospheres excess pressure), dehydrolinalool
Card 1/3 and its analogues resulted almost quantitatively. These com-

SOV/79-29-3-4/61
Synthesis of Analogues of Geranyl Acetone and Pseudo-ionone
pounds were transformed by partial hydrogenation over a
Pd-catalyst into linalool and its analogues (Ref 3). The
three methods used for the synthesis of the ketones of the
isoprenoid type were also employed for the synthesis of
various analogues of geranyl acetone (Scheme 1). The syn-
thesized analogues of geranyl acetone are shown in table 2.
The synthesis of the pseudoionone analogues was carried out
according to the methods B and V. In heating the analogues
of dehydrolinalool with acetoacetic eater the analogues of
pseudoionone were formed (Table 3) (Scheme 2), in yields
of 50-70o. The pyrolysis of acetoacetates of the dehydro-
linalools preponderantly leads to one of the pseudoionone
isomers; the other is obtained but in small quantities which
is not the case with the pseudoianone analogues (XVIII~ and
(XX), where two stereoisomeric forms (Table 3) were separated
in form of their hydrazones. The compounds synthesizee are
characterized by absorption spectra in the ultraviolet range.
There are 3 tables and 7 references, 5 of which are Soviet.
ASSOCIATION: Moskovskiy institut tonkoy khimicheskoy tekhnologii
Card 2/3 (Moscow Institute of Fine Chemical Technology)

SOV/79-29-3-4/61
Synthesis of Analogues of Geranyl Acetone and Pseudoionone
SUBMITTED: January 23, 1958
Card 3/3

5 (3)
AUTEORS: Makin, S. M.,11ochalin, V. B.,
/7,
-STFP-vrygina, 0. A., Nazarova, D. V., 11azarov, I. Deceased)
TITLE. Synthesis of +hp Analogs of Nerolidol, Farnesil Acetone nd
Geran-1 Linalcal (Sintez analogov norolidole, fnrnezilatsetana
V
i geranillinaloola)
PERIODICAL: Zhurnal obshahey khimii, 1959, Vol 29, Nr 4,
pp 1176-1182 (USSR)
ABSTRACT: In the present paper the authors investigated thoroughly
the synthesin.of isoprenoid alcohols and -ketones (of the
analogs of the above-mentioned products) and of the inter-
mediate products according to the given scheme. The
condensation of the analogs of geranyl acetone (a) with
acetylene was carried out in the steel reactor at 0-200 anO
at 3-10 atmospheres exceog pressure in the presence of
powdery caustic potas'. The yield of tertiary acetylene
alcohols N was 80-85 %. The condensations hitherto used
(Refs 5, 6) are vnrv nomplinated. All analogs of dehydro-
nerolidol (b) syn.hasized in this investigation are
presented n table 1. According to previous experiments
Card 1/3 (Ref 7) it whs possible to carry out the hydrogenation of the

Synthesis of the Anrlogs nf IT--arneoil
Acetone and Geranyl Linn!-)6L
ric,~tyl.;ine rlcol,oln. obtitined, thi oi'
rC
(b), in the of tihe
nerolidol (V) obtpin,~d b,., pnrti-.tl hy:, 1~ tyl one
111'rohols (b) vii th this cstaly~.;t ;~r- -'Iven in t-bl!! 2. Accor('in(5
to the reaction rtit,. catril.-i-.3to (Pmcrilbed in rt~f-:,2-cncn F3 thf!
authors were able er.rlicr to carry out th-2 rcaction of 0
terti,,--ry vin-:l -lrohol.~~ --ith aceto,,;~cetic ester nat 1 )C-1~~)
also without catalysts, and obt-r3ined in this methyl
heptene, geranyl ;tcetone, and their analor.,s (Rcf!-, 1, 2). In
the present study they applied this method to the nynthesis
of the analogs of fr~rnesil acetone (C). When heating the
nerolidol Pnalogs ~oscribed above (Table 2) with cetoncetic
eater at 180-2000 the analogs of farnesil acetone (g) were
obtained (liable 3). The analogs of farnesil ncetone (g)
synthesized were then condensed with acetylene. The resultin,c-
tertiary acetylene alcohols (d) were converted by partial
hydrogenation on Pd/Ca!--O- into the analogs of gerinyl linalo6l
(e) (Tables 4 and 5). The compounds obtained cmil,i be used in
Card 2/3 the synthesis of the correspon-ding -.na!,Dgs, the rhytol, a

3ynthesio of the Anologs of Nerolidol, Farnesil
Acetone nnd Geranyl Linalobl.
constituent of vitamins K and E.
8 references, 6 of which are Soviet.
ASSOCIATICN: Moskovskiy institut tonkoy khimicheakoy
Lomonosova (Moscow Institute of Fino
imeni Lomonosov)
SUBIMTTTED: March 28, 1958
30V/79-29-1-?9/77
There 5 tables and
tekhnologii imeni
Chemical Technology
Card 3/3

5.3400
77868
SOV/79-30-2-19/78
AUTHORS: Nazarov, I. N., Makin, S. M., Shavrygina, 0. A.,
Smirnyagin, v. A.
TITLE: Synthesis of Higher Fatty Acids and Alcohols From
Tertiary Vinylearbinols
PERIODICAL: Zhurnal obshchey Ichimil, 1960, Vol 30, Nr 2, pp
443-450 (USSR)
ABSTRACT: The higher unsaturated acids were synthesized
using acetoacetic and malonic esters. Diesters
(III, R - CH RI-OC H ), (XV), (XXII) and (XXIX)
were obtaine4 by rhc~ing sodium derivatives of
malonic or acetoacetic esters with the respective
bromides (see schemes I and 2 for designations
and for synthetic routes).
Card 1/7

77868 SOV/~9-30-2-19/(8
Scheme 1. Synthesis of higher fatty acids and alcoholz.
Card 2/7
Na -CRCOCHS CH BE CH
~
~

CH3Br RON H
fo 14
~o
(VII) (VM) Ux)
CONS
I iHBr
COOCINI
CHZ-CH t
I CHICOCHI
C00CtH5
CHZBr

if

M MY,

0
COON
1.
61 ~COOCZN,
CH
coo Cos
2. NCI
CH
04.
1 UAIH4
'Co0y

N
CH,OH ,
-CH
61, '-C00CJHj
(XIX) w'; Pd (Mil) Ifl;ML (XVI) i

77868 SOV/79-30-2-19/-(8
fj) T- I-X; M) L
CH,OH /"-/COON
HBr (MV)
CH3Br mac'li cooc:M5 COOC,H,

CH
cooczH,
61
~cooczmj
ooa)
COON
UAIN, CH20H
(=V)

cec, HI;Pd
(xx)
0
0 H
ON - U,
(Xxv) (XXVI I
(XXVII)
~octms /cooct", COOH
CH
I
u1

Card 3/7 (MM) CO
(M)

Synthesis of Higher Fatty Acids and Alcohols
From Tertiary Vinylcarbinols
77868
SOV/79-30-2-19/78
Scheme 2. Synthesis of geranylacetic acid and
of its analogues.
R R cow R CORI
CH%Br I",-CO5C'H'
CH 95VICION
R COOM LtAIH4 CH'OH
(V)
It =CHI 'CtH5 'Cl OCZHS CHI
The diesters were converted by successive saponification
and decarboxylation into (2, 6-dimethyl-2,6-decadien-
Card 4/~ -10-oic (geranylacetic) acid (IV, R -CH 3 ), 6-methyl-

77-
Synt lesl:~ of ~111.1-iier
Eilrcm Tertiary Vinylcarblriol-
-2,b-decadieri-10-oic acid (XII),
-tetradecutviev,-14-olc acid (XXIII)l arld 'j, io, 14-
- -I.-rimethyl-2,6-10, 14 -oc tade eate tri,~n-18-ol c ac-ld
(XXX) . The table below lists the constant.; of 1;1~iu
synthe:Azed acidt; w1th the com;tantL~ of their, S-
~-ults. The hl(rher alcollcil:;
were obtained by VIL-ULICU16 tile VeL;pf:'-'UVC W-'Ids
wit.lh 11thLum 'aluminurn hydr-Ide (2 0--dlrn(Ah,,,j1-2
6 '1
-decadien-10-ol (V), bp '[2-74 mm),
n2o 1.4740, d2 Q0-67t)G; 6-mctliyl-2,()-d(,cadi(2i,-'-O-(~I
D 11 20 2 0
) I -, D1 .1171 , d
(XIII), bp b4-660 (0.03~ mm I ~j
0.8720; (-;,10-dlmeti-iyl-2,6,10-tetradec!atrlc-it-1111-cI
(XXIV), bp 123- 12~o (0.4 mm), n 20 1.4845, d 0.
D
or, by hydvo_~,enatiGn of unsaturated alcohols (e.-,
6-methyl-10-decanol (XIV), bp 114-11~O (4 mm),
11 20 1.4416, d 20 0.83119). Saturated acids were
Card 511 7 D 4

S,vrj,-;jesis ot' Higher Fatty Acids arid Alcohols 77868
U.
FI-on Tertiary Vinylcarbinols SOV/~9 -3 0-2 - 1
Table 3. Constants of higher fatty acids.
Key to Table 3: (1) Acid; (2) bollin-P point
(pre3sure in rrim); (3) found; (11) calculated;
Cormula; ((.,) yield (In %); ('() S -L)cnzy1pseudo-
LhIUVOIULIrnoult; bolling point.
moo 7 1.
(2) J w -
of (J-1
D (5
) C i H 1 C. H Al

(it I 11~-11113 12.5- 12r 1.4735 - C1214.111 1 [3- 114- (:VI1,O,N,S 7.8b. 7.7-1
1
. 124-121 Of 1.47:10 7.74
1\111 125-127 0) 1.4684 0.9419 M.77 M-57 Gillil'ol 72-5j. 11 'N,. 72.5_1 n44 I I i- I 1." 19. M."i
72S5 9
1 .95
111AP-02 1.48421 O.W24 76.61
7b
-29 C,411~(), 10-S:..
77A)I. 1
12 111
77
% 71;.84 10.16
(N N 1."t-162 AMC U.9263 q?,77 98JG Cq, II,,f 1, .
-
VIA I. I IM. 111.11 141.71 V) MI-M
:,Ii S ,"M 3. -, 7

(1% It !0.1,121
I w- Nq 1:111 1 `111
11.9213
61111 1
62,43 13 11.117
-
-
117-11S
:
N 5

ji, 7M
: T84
1 1 1:t-M i~.Iij 1.4") 10-721 N4.1#6 1 :A. 67 C , I I ,I ),UI 3N 116--117 IN,,S! fi.qO 7.31

Notes to Table: *T he y.Lr-_!ld lo 1, -:iscd on the Lei-t 1ar,,
ole-Cinic alcohol
Ca.imj 6/7

Synthesis of Higher Fatty Acids and Alcohols 77868
From Tertiary Vinylearbinols SOV/~q--~O-2-iq/78
ASSOCIATION:
SUBMITTED:
obtained from the previously hydrogenated diesters 0
(e.g., 6-methyl-10-decanoic acid (XVII), bp 128-129
(3 mm), n201.4548, d 20 0,9209). There are 1 table;
D 4
and 9 references, 7 Soviet, 1 Germar~ 1 U.K. The
U.K. reference is: M. 0. Forster, D. Cardwell,
J. Chem. Soc., 103, 1346 -(1913-).
Moscow Institute of Fine Chemical Technology (Moskovskiy
inetitut tonkoy khlmichskoy tekhnologii)
February 4, 1959
Card 7/-(

5/079J60/030/05/15/074
B005/BI26
AUTHORBs Makin, S. M., Mochalin, V. B., Nazarova, D. V.
TITLEs Ring Closure of knalogs of Pseudoiononeland Citrall
PERIODICAM Zhurnal obahchey khimii, 1960, Vol. 30, No~ 5, PP. 1471-1476
TEXTt The authors examined the ring closure of five previously (Ref. 11)
synthesized analogs of pseudoionone with different gem,-substituents in
position 1. The reaction scheme of this ring closure is given. The ring
closure was carried out with the help of two standard methodst 1) Ring
closure under the effect of boron trifluoride in a benzene solution at
-50- With this method the relevant a-ionone is produced. 2) Ring closure
by the effect of a mixture of concentrated sulfuric acid and acetic acid
at 10-150- A mixture of c(- and ~-ionone is produced by this method. The
products were identified by the analysis of their ultraviolet absorption
spectra. Table 1 shows the results obtained by ring closure by method I).
The analogs of pseudoionone with the following gem.-substituents R in
Position I were examined% R - H; C2H 5; iso-c3H7; tert '-C4H9; Cl. The
Card 1/3

Ring Closure of Analogs of Pseudoionone and s/o79/60/030/05/15/074
Citral B005/B126
above table shows boiling range, refractive index, A MaX9 6..X q yield
and results of the C,R-determination for each of the products 6~tainsijy ring
closure. 2.4-dinitrophenylhydrazones were produced from the resulting
analogs of a-ionone. The table also gives melting point, A max , and
nitrogen content of these derivatives. Table 2 gives the results obtained
by ring closure by method 2). Both analogs of pseudoionone with the
substitueInte R - H and R - Cl gave no ring closure by either method,
since the activating energy neoeaaary to form the carbonium ion, which
is an important intermediate, is in both cases too high. The authors
also examined ring closure of some analogs of citral, which were previous-
ly (Ref. 13) synthesizedo In this case ring closure was brought about by
the effect of sulfuric acid on the Schiff's base of the citral analog
(Ref. 14)- Mixtures of ot- and A-cyclocitral were thus formed; the re-
action scheme is given. The analog with R - H gave no ring closure here
either, While the Schiff's base of the compound with R w Cl split off
under the effect of sulfuric acid H01, and changed into a cyclic product,
whose structure was notdetermined. Table 3 gives the results obtained
from the ring closure of the citral analogs. All the ring closures
Card 2/3

Ring Closure of Analogs of Pseudoionone and S/079/60/030/05/15/074
Citral B005/B126
carried out are fully described in the experimental part. There are
3 tables and 16 references: 4 Soviet, 6 English, I German, 4 Swiss, and
1 Czechoslovakian.
ASSOCIATIONt Moskovskiy institut tonkoy khimicheskoy tekhnologii
(Moscow Institute for Fine Chemical Technology)
SUBMITTED; May 21, 1959
Card 3/3

84876
S/07 6o/o3o/oi0/016/030
B001YBo66
AUTHORS: MakiEl-S.M. and Kruptsov, B. K.
TITLE: Chemistry of Unsaturated Ethers. V. Acetals of Vinyl
.Ltaldehydej. A New Method of Synthesizing I-Alkoxy-
dienes-1,3 I
PERIODICAL: Zhurnal obs chey khimii, 1960, Vol~ 30, No. 10,
pp. 3276 - 3280
TEXT: The authors of the present paper investigated the autocondensa-
tion of vinyl ethyl',jvinyl butyl, and vinyl isoamyl etherslin the pres-
ence of BF.,,, -O(C,H5)2', in the comple with HgO,Hg(OCOCH 3)2) HgS04* HgCl
1 1 2'
of FeCl 3 in the complex with HgO and%g(OCOCH 3)2, and of ZnC'2 in the
complex with HgO. Acetone, dimethyl formamide, diethyl ether, nitro-
methane, and acetophenone were used as solvents. The autocondensationq
was most efficient in acetone or diethyl ether when using BF '0(c H5).
3 2 2
in the complex with HgO or Hg(OCOCH 3)2 . The acetal of vinyl acetaldehyde
Card 113

84876
Chemistry of Unsaturated Ethers. V. Acetals Sl079V601030101010161030
of Vinyl Acetaldehyde. A New Method of B001/ 'D 066
Synthesizing 1-Alkoxy-dienes-1,3
and a small amount of condensation products of this acetal with vinyl
alkyl ethers was thus obtained. In the absence of BF 3* O(C2 H5)2' HgO
and mercury acetate are ineffective. On the other hand, vinyl alkyl
ethers are known to polymerize readily in the presence of BF 3* O(C2 H5)2'
so that the autocondensation was assumed to take place in two stages,
first under the formation of an acetal acylal (III) (Ref-4) which is X
added in the second stage to the other molecule of the vinyl alkyl
ether by means of the catalyst (Refs.5--7) (Scheme 2). The autocondensa.
tion of vinyl alkyl ethers by means of HgO + BF 3* O(C 2H5)2 obviously
takes place according to Scheme 3. The resultant acetals of vinyl acetal-
dehyde are added to a molecule of the vinyl alkyl ether, thus forming
1,T,3-trialkoxy COMDounds (VI) (Scheme 4). This reaction, however, pro-
ceeds slowly and with low yields of the compounds (VI). The highest
yield was 246. The infrared spectra of the autocondensation products of
vinyl ethyl and vinyl butyl ethers showed frequencies characteristic of
the vinyl group (CH2~CH-) (Ref.9). The spectrum of the diethyl acetal
Card 2/3

8h876
Chemistry of Unsaturated Ethers. V. Acetals S/079~60/030/01 o/ol 6/030
of Vinyl Acetaldehyde. A New Method of B001/ 066
Synthesizing I-Alkoxy-dienes-1,3
of croton aldehyde shows an absorption band characteristic of a sub-
stituted Vinyl group (Ref. 9). When passing acetal vapors of vinyl
acetaldehyde in vacuo at 3500C over the acid catalyst MSHPO 4' 1-alkoxy-
butadiene-1,3 (VII) resulted (Scheme 5)- With maleic aldehyde, the
1-alkoxy-dienes-1,3 gave the adducts (VIII). Their hydrolysis (Scheme 6)
yields crystalline alkoxy-tetrahydrophthalic acids (IX). There are
12 references: 9 Soviet, 2 US, and I Japanese.
ASSOCIATION: Moskovskiy institut tonkoy khimicheskoy tekhnologii
(Moscow Institute of Fine Chemical Technology
SUBMITTED: December 7, 1959
Card 3/3

MKIN9 S.M.; ROZHKOV, LNO
Chemistry of unsaturated ethers. Part 6: Condensation of acev--16
with 1-alkoxydienes. Zhur.ob.kbim. 31 no.10:3214-3220 0 161.
OURA 14:10)
1. MoskovokLy institut tonkoy kbimicheskoy tekbnologii imeni
M.V.Lomonosova.
(Acetals) (Mefins)

MAKINS S.M.; ROZHKCV, I.N.
Chemistry of unsaturated others. Part 7: Addition of
-aldebyde acetal to I-ethoxy~-2-methyl-1,3-butadiene. Zhi=.ob.
khim. 31 no.10;3319-3323 0 161. OMIA 14:10)
1. Maskovskiy institut tonkoy khimicheskoy tekhnologii imeni
M.V. Lomonosova.
(Aldehydes) (Butadience) (Ethers)

MAKIN. S. 14,
Wbr method of producing polyene aldehydes. Dokl.AR &WR 338 no.2;
387-389 Vq 161. (mm 14:5)
1- MOSkOVskiy instituttbnkoy Ichimicheakoy tekhmlogii im. mv.
Lomonooova., Predstavleno akademikom I.V.Kmmyantsem.
(Aldehydes)

MAKIN, &M4--7ELEGINA, N.I.
Chemistry of unsaturated ethers. Part 9: Alkoxylation of furan.
Synthesis of dialdehydes and glycols. Zhur.ob.khim. 32 no-4:
1104-1.111 Ap 162. (MIRA 15-34)
1. Moskovskiy institut tonkoy khimicheskoy tekhnologil.
(Furam) (Alkoxy groups) (Glycols)

MAKIN, qjjj NAZAROVA, D.V.; KIRSANOVA, E.A.; SMIRNOVA, L.N.
Chemistry of unsaturated ethers. Part 10: Addition reactions of
1-alkox.v-1,3-dienes. Zhur.ob.khim. 32 no.4:lUl-Ul6 Ap 162.
(MIRA 15:4)
1. Moskovskiy institut tonkoy khimicheskoy tekhnologii.
(Unsaturated compounds) (Alkoxy groups)

,,_MAK ~IN ~j NAZAROVA, D.V.
Chemistry of unsaturated ethers. Part 3-1: Synthesis of poljene
others based on I-alkoxv-1,3-dienes. Zhur.ob.khim. 32 no.4:
1117-1119 Ap 162. (KIRA 15:4)
~. Moskovskiy inatitut tonkoy khimicheskoy tekhnologii.
(Unsaturated compounds) (Alkoxy groups)

MWN, S.N.j KRUPTSOV., B.K.
Chemistry of tmsaturated others. Part 12.- Stawtural orientation
of dienis condensations of 1-alkoxydienes with asy=etrical
dienophylso Zhur.ob.7chim. 32 no.8:2521-2527 Ag 162. (MIU 15:9)
1. Hookovokiy institut tonkoy khimicheokoy tokhnologii imeni
M,V. Lamonosovae
(Butadiene) (Ethers)

MAKIN, S.M.; KRUPTSOVP B.K.j MEDVEDEVA, V.M.; SMIWVA,-'L.H.
Chemistry of unsaturated ethers. Part 13: Reaction of acetalization
of 1.1.3-trialkoxyalkanes and the synthesis of 1-alkoxy-1.3-dieneo
with heavy alkoxy groups. Ultraviolet spectra and Raman spectra
of 1-alkoxy-1,3--dienes. Zhur.ob.khim. 32 no.8:2527-2535 Ag 162o
(MIRA 15:9)
1. Moskovokiy institut toikoy khimicheskqy tekhnologii imeni M*V.
Lomonosova.
(Butadiene-Spectra) (Aikksr

Maw., S.M.
Chemistry of unsaturated ethers. Part 14: New method of
preparing retinene (aldehyde of vitamin A). Zhur.ob.kh:Lm.
32 no,10:3159-3161 0 162. (MIRA 15:11)
1. Moskovskiy institut tonkoy khimiohaskoy tekhnologii
imeni M.V. Lemonosova.
(Retinal) (Ethers)

MAKIN S H ; SUDAKOVA, V.S.
Chomiatry of wwaturated others. Part 15: Telomerization
of vinyl ethyl ether with acetaldehyde acetal. Synthesis
of 1-alkoxypolynnes. Zhur.ob.khim. 32 no.10:3161-3166
0 162. (MIRA 15:11)
1. Moskovskiy institut, tonkoy khimicheskoy tekhnologii
imeni M.V. Lomonosova.
(Ethers) (Acetaldehyde) (Polymerization)

M~IN, S.M.; ROZEKOV, I.N.; SMAKOVA, V.S.
Chemistry of unsaturated ethers. Part 16: Telomerization
of 1-alkoxy-1,3-dienes vith acetals of unsaturated aldehydes.
Zhur.job.khim- 32 no.10:3166--3170 0 162. (KIRA 15:11)
1. Moskoviskiy institut tonkoy kbimicheskoy tekhnologii
imeni, M.V. Lomonosova.
(Unsaturated compounds)
(Acetals) (Polymerization)

SHAVRYGINA ik O.A.; MAKIR, S,.X.
Chemistry of unsaturated ethers. Part 17: SWthesis of acetals
of aryl polyene, aldehydes. Zhur.ob.khim. 33 no.10:3176-3180
0 163, (MIRA 16M)
1. Moskovskiy institut tonkoy khimicheakoy tekhnologli im. M.
V,Lomonosma.

R02HKCVf IX; MAKIN, -S. M.
Interaction ofd, P -unsaturated ketones and esters with metallo-
organic compounds. Zhur.ob.khim. 34 no.ls59-65 Ja 164. (MIRA 17:3)
1. Moskovskiy institut tonko
,y kbintichaskoy tekhnologii imeni. Lomono-
sova.

MAKIN, S.M.; LAPITSKIY, G.A.; STRELITSOV, R.V.
Chemistry of unsaturated ethers. Part 18s Synthesis of unsaturated
dialdehydes and their derivatives. Zhur.ob.khim. 34 n-o.l165-70 Ja
164. (MIRA 17:3)
1. Moskovskiy institut tonkoy khimichaskoy tekhnologii imeni Lomonosova.

LAFITSKIY, G.A.; MAKIN, S.M.
Synthesis of polymeric Schiff bases with a system of conjugate bonds.
Zhur.VKHO -9 no.1:1-16-117 164. (MIRA 17:3)
1. Vbskovskiy institut tonkoy khimicheskoy tekhnologii imeni
Lomonosova.
tit",

MAKIN, 3. M. V. I'll.; r~';"INA, M. 1,
3
.?f al.6co.,.-y-4 --3-i,~plropyrans (L:y-- -4 -7 ac,~
glu rarona L-:Iehyde) . Zhux. ob. inim. 34 no.6~1&)(~-1?15 ~"e
IV'.~A
Imst tut torikoj K~.iml-tioskoy tekfinologi~ imenl Lomono-
sollrpl.

~~jj~ -1- ~~, -------------

V.M.
S..M,; LIKHOSHERSTOV,
5 thesis of dianila of elutaconic aldehyde from 2,6-dialkoxy
P-dihydrnpyrans. Zhur. org. khim. 1 no.4:-640-643 Ap 165.
(MIRA 18:11)
1. 14oakovskly institut tonkoy khimicheskoy tekhnologii imeni
1,)vicnosova.

~11 A K 7ti I I Ki:
viral a t i -,, A ty c~ f
I - p - - . ..I
larivai-lves). Fa!-m. I r. .!.~J,4,1') .;a - F
9 y n!l i-,:.-on~ c 'i,. a d z P Mo c v:- -I
on k- C, y k .; y

ACC NR: AP6031299 SOURCE CODE: UR/0366/66/002/009/1586/1589
AUTHOR: Shavrygina, 0. A.; Nazarova, D. V.; Makin, S. M.
ORG: Moscow Institute of Fine Chemical Technology im. M. V. Lomonosov (Moskovskiy
institut tonkoy khimicheskoy tekhnologii)
TITLE: Chemistr-y of unsaturated ethers. XXIV. Preparatioa ofvitamin A ethers
SOURCE. Zhurnal organicheskoy khimii, v. 2, no. 9, 1966, 1586-1589
TOPIC TAGS: vitamin ether
ABSTRACT. Ethyl ether of vitamin A (bp 144-1470C, n10 1.5735)was
obtained by the following reactions:
C113
(CH,CO),NBr I
CHf'=C"-C=CIIOC2'16 BrC113C11=C-C11(OC2H3)I
CJ1,0H
U113
H+ HGaCLI
HSC2OCHjC11-=C-CH(OC2"1)3 H&C-.0G112CH=C-CHO
&3 CH3
(IV)

ACC NRt
OH
HfClQCH2CII=C-CH-CMCH
M
C',
CHS 3
H-CH-~=O HCaCL( CH=CH-C-C.=-U"
(VII)
(V) ONI
Cl'3 CH3
CII=CH-C C-G-CH-LCII-CH2OC2HS
Oil OH
(Vill) LIAM.
C113 CH3
U-CH-c"-
Preparation of -the starting 'compounds ib ed
(WA-50; CBE No. 121
Card 2/2 SUB CODE; OT/ SUBM DATE:

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wntwupds ages'O
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14
UrOO

M"UrVA, F. A.
125?. Ogrardzats4a ucheta raskhoda matektalov v bor'be za ikh ekonomiyu i
snizhentye sebostoimsti pron7qj~lennqy produktail. (Na opyte predlpriyatiy
mestnoy prom-sti g. Leningrad4j. L. 1954. 209. 203M. (M-vo V_yssh. obrazovanlya
SSSR. Leningr. Fin-ekon. in-t). 100 ekz. B. t9. - f54-,cl634_/
SOi Knizhnaya Letopis, Vol. 1. 1955

2/5CT 29
.0
Synthesis
erivation of Alcohols by the Grignar-d. Method'$~=
OM -Oxides; III 'Synthesis of Pr0py4Soprqj*1C%p-
lsopropyllsobutylcar~b-~ W12 ~ _(II)-and: Iso-
6pyibutylcarbinol (my Fran Isdamilezie Oftide,",
,S.~ YAaimyekiy.,. B. N., Konevichem, stud, 3 pp
bur Obahch Khlm" Vol XVIII,, No 10
mWlene oxide reacted with ethylusineiium btopdd#,
1magnesium bro~lde, and isdjropy1wguesi= bro-
g;Lve -alcohols I,'jr, and III ;rom leowWlene
do'* i**%ted I Oct k7-
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KAMSKIT, I.Z., kandidat takhnichaskikh nauk.
116;,u
Using sea water for supplying steam boilers and vaporizers. Acirb.
neft.khox.33 no-1105-38 9 156. (KaA 10:4
(sea water) (Feed water)

MEINSKIY, I.Z., kandidat tekhnicheskikh nauk.
MWANAMON _j 1
Preventing scale formation in vaporizers operatini, on Caspian
Be& water. Azerb.neft.khoz. 36 no.1:28-31 Ja '57. (KLRA 10:5)
(Food-water purification)

MAKINSKIY, I.Z.
~ --- Z~
Thermochemical method for softening sea water. Izv.v7s. uchelb. zav -
neft' i gaz no.4:95-103 '58. (MM ll:;~
l.Azarbaydzhanakiy induatriallnyy institut im. M. Azizbeko7a.
(sea water)

KAKINSKIY, I.Z.
,e,-~~PbssZble designs of high and extrahigh pressuze boiler-units
using highly mineralized water. Azerb. neft. khos. 37 n0.3:35-38
Mr 158. (KIRA 11:8)
(Boilers)

10(4), 5(4)
AUTHORSt Makinskiy, I. Z., Simonov, P. P. SOV/152-59-3-19/25
TITLEs On the Problem of the Influence of the Salt Content of the
Liquid on the Ascending Velocity of Gas and Vapor Bubbles
(K voprosu o vliyanii solesoderzhaniya zhidkosti na skorost'
pod"yema puzyrikov gaza i para)
PERIODICALt Izvestiya vysshikh uchebnykh zavedeniy. Neft'f i gaz, 1959,
Nr 3, Pp 83-90 (USSR)
ABSTRAM The experiments were partly carried out with single bubbles
introduoed from below from calibrated glass nozzles into a
1500 mm high glass tube filled with the liquid to be investigate(%
partly by bubbling up the surfao,5 of the liquid through boiling
or pressing air through. Solutions with varying concentration of
NaCl, Na 2so 40 MgC12 and MgSO4 were investigated. A number of
experiments was carried out under the addition of isoamyl
alcohol for the purpose of investigating the effect of surface-
active substances. In order to determine the influence of
insoluble colloids, disperse Mg(OH)
was formed out of an
2
addition of NaOH and MgSO 4* With increasing NaCl-content
Card 1/4

On the Problem of the Influence if the Salt BOV/152-59-3-19/25
Content of the Liquid on the Ascending Velocity of
Gas and Vapor Bubbles
the capability of the air bubbles to unite decreases and
ceases at approximately 5 9/1 so that a large number of fine,
slowly ascending air bubbles forms. At a salt content of more
than 25 9/1 the capability of uniting returns and becomes
especially conspicuous at contents over 40'gli. For the
ascending velocity w of a gas bubble the simplified formula
X _d
w - 3.6.71-7 is set up (w a the ascending velocity in m/sec,
d - the diameter of the gas bubble in m. V. Levich (Ref 3)
2
d
suggested another formulat w specific weight
Fl
of the liquid,,/4 is not explainedr. Experiments showed that in
the case of lower salt contents the ascending velocity follows
the formula by Levich, in the case of higher salt contents,
however, it passes over into the curve according to the first
formula after a steep descend. The delay in velocity cannot
only is explained by viscosity. Surface-active substances
Card 2/4 accumulate in the cover of the gas bubble and the velocity of

On the Problem of the Influence of the Salt SOV/152-59-3-19/25
Content of the Liquid on the Ascending Velocity of
Gas and Vapor Bubbles
the bubble approaches that of a solid body. By proper dosing
of isoamyl alcohol the velocity can be reduced to a constant
value (-15 cm/sec), independent of the salt concentrationj
it will correspond to that of a solid ball. It is also
possible to assume the solution to be a solution of water in
sa~ It becomes obvious that with ir-;,reasing salt content
the conditions of circumflowing deteriorate tu begin with,
later, however, as soon as the composition of the surface
film approaches that of the liquid the affect of the salt content
decreases. In the surface film a supersaturation occurs under
the formation of insoluble colloids which reduce the velocity.
In the case of bubbles of a diameter being more than 1 mm
deviations occur as a result of deformation. On'boiling, the
bubbling also depends on the tendency of the vapor bubbles
towards flowing t^gether. NaCl shows with colloidal Mg(OH)2
an intensified bubbling between 5-10 9/1, where flowing
together ceases. The explanation for this: the colloidal
Card 3/4 parts form quasi-solid bubble covers which render flowing

On the Problem of the Influence of the Salt SOV/152-59-3-19/25
Content of the Liquid on the Ascending Velocity of
Gas and Vapor Bubbles
together more difficult at certain salt concentrations. At
higher salt contents the oolloide coagulate, no formation of
covers takes place and the bubbles can flow together again.
The same problem had already been investigated by A. Frumkin,
V. Levich, B. Gorodetskaya and others. The effect of substances
solved out of the wall of the vessel was detected by
T. A. Kryukova (Ref 4) and S. A. Durov-(Ref 5). There are
6 figures, 2 tables, and 7 Soviet references.
ASSOCIATION: Azerbaydzhanskiy industriallnyy institut im. M. Azizbekova
(Azerba,ydzha. Tri&j trjaj~ jWtitute meni M. Azizbekov)
SUBMITTEDt December 22, 1958
Card 4/4

MAKINSKIT. I.Z.; SIKOHDV, P.P.
Supplying steam to petroleum refineries. IZT*VYS*ucheb.zavo;
neft' i gaz 3 no.2:87-94 160. (KM 13:6)
1. Azerbaydzhanskiy institut nefti t kbimii im. M.Azizbekova.
(Stea-)

MAKINSKIY, I. Z.
Doc Tech Sci - (diss) "Softening of sea-water and the problem of
its utilization for supplying boilers operating at high and at
superhigh pressures." Moscow, 1961. 34 pp with diagrams; (Acad-
emy of Sciences USSR, Power Inst imeni G. M. Krzhizhanovskiy);
200 copies; price not given ; list of author's works at end of
text (14 entries); (KL, 7-61 sup, 230)

MAKINSKIY, I.Z.; SIMONOV, P.P.
Supplying steam to chemical plants and petroleum refineries.
Izv, vys. ucheb. zave; neft' i gaz 5 no.3:75-78 162.
(MIRA 16:8)
1. Azerbaydzha-nskiy institut nefti i khimii imeni M. Azizbekova*

L 45613-66
FXCC NR, CODE i _MWOL "36610MIWfIO!131611_!~~)
AUTHOR3 Makinskiyp I. Z. (Professor, Raciaw, Doctor of Technical Sciences);
Abdullayev-,-r.-K.-Cx-,rn-gi-neer)
ORGj Azglavenergo
TITLEs Methods of selecting vaporization stages of optimum efficiency for boilers
with stage vaporization
SOURCE3 IVUZ. Energetika, no. 7, 1966, 113-115
TOPIC TAGS: steam boiler, vaporization, ayelzae, industrial separator,
water vapor, calculation
ABSTRACTt Four-stage vaporization stages with inside cylindrical cyclones in the
first stage and outside cyclones in the other stages were studied because there is no
common method for determining the load distribution among the vaporization stages.
The solution is sought by the analytic method. A system of equations is set up and
formulas for optimum throughput of the vaporization stages and for relative quality
of the vapor are obtained. The calculation results show that the throughput of the
first, second, third, and fourth vaporization stages is 569 26.1p 12.2, and 5.7'p,
respectively. The principles presented in this study make it possible to analyze the
effect of various factors on the load distribution among the vaporization stages of
boilers. Orig. art. has: I figure and 17 formulas.
SUB CODEi 131 SUBM DATEs IlDec65/ ORIG RKFs 002
Card i /i mia - nnr A91 _1AA A4A91 _1A

SOV/25-58-12-38/40
AUTHOR: Makinskiy, T.A., Learned Secretary
TITLE: The E idemical Encephalitis (Epidemicheskiy entse-
falit~
PERIODICAL: Nauka i zhizn', 1958, Nr 12, pp 75-76 (USSR)
ABSTRACT: The symptoms of the
described, as well
it.
ASSOCIATION: Inatitut nevrologii
SSSR (The Institute
of Medical Sciences
encephalitis lethargica are
is the medicine used to fight
Akademii meditsinskikh nauk
of NeuroloF of the Academy
of the USSR
Card 1/1

SHMIDT, Ye.V., prof.; KAKINSKITp
Studies on vascular diseases of the nervous system in the Soviet
Union in 1958; based on data from the first conference on research
planning and coordination conducted by the Inatitate of Neurology of
the AcadeaW of Medical Sciences of the U.S.S.R. in November 19571
Iseledovanita v oblasti sosudistykh porazhenii nervnoy sistemy v
Sovetskom Soluse v 1958 g.; po materialam pervogo soveshchantia po
planirovanitu I koordinatait nauchnykh iseledovanii, provedennogo
Iostitutom nevrologii AMY SSSR v noiabre 1957 g. Vest. AMY SSSR
13 no.4:63-68 158. (KIRA 11:4)
(BRAIN. blood supply
dis., review (Ruse)

KAUNSKIY, T.A.
1, -
First conference on the coordination of Soviet research on vaacular
affections of the nervous systeme' Zhur.nevr. I paikh. 28 no.9:1154
'58 (mm 11:11)
(MMVOUS STSTEK-BLOOD SUPPIT)

YAKINSKIY, T.A.
Acute disorders of the cerebral blood circulation. Vest.AMU
SSSR 14 no.7:68-75 '59. (MIRA 12:9)
(BRAIN-BLOOD SLTnY)

MA-KINSIKff , T.A. --I.t,.--,-
Out-of-town session of the listitute of Meurology of-the AcadexW of
Medical Sciences of the U.S.S.R. Zbur. nevr. i paikh'59 no.3:377-378
'59. (IMBA 12:4)
(BRAII-DISFASYS) (POLIOWSLITrS)

MAKINSKIYq T.A.
Joint session of the Institute of Neurology of the Soviet
Academy of Medical Sciences and the Kiev Medical Institute.
Zhur. nerv. i psikh. 60 no. 12:1695 160. (MIRA 14:4)
(NERVOUS SYSTEM-DISEASES)