SCIENTIFIC ABSTRACT KIRSANOV, A.V. - KIRSANOV, A.V.
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December 31, 1967
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SCIENTIFIC ABSTRACT
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30V/79-28-6-36/63
The Diphenylamide of Trichlorophosphazocarbonic Acid and Its Derivatives
phenylurea at 70 - 80 0 in carbontetrachlor.lde solution al-
most quantitatively under the formation of the diphenylamide
of trichlorophosphazoaarbonic acid according to the scheme
(C6H5)2 NCONE2 + PCI5 0 2HC1 + (C6 H5)211CON'PCl3 (I)* This
diphenylamide is on the one hand ar, analogue of the recently
synthesized triohlorophosphazoacyl (Ref 3) and on the other
hand it is an analogue of the dialkylamides of trichloro-
phosphazo sulfuric acid (Ref 4). The compound (I) is a low-
-melting product whioh only in high vacuum remains undecom-
posable in distillation; it hydrolyzes easily with water and
violently enters reaction with alcohols~j~henols and amines.
On the action of.,~nhydroua Tormic acid con3equently
yields all theoretically possible phosphorus-containing prod-
ucts of hydrolysis, depending on the conditions of the re-
action : the dichloroanhy&ride of the H..N-diphenylcarbamide-
-NI-phoaphoric acid (C H ) NCONHPOC1 (II), the monochloro-
anhydride of the NlN-d~pRer2~Icarbamige-.Iil-phospboric acid
(C H ) NCONHPO(OH)C1 (III) and the free N,N-diphenylcarbamide-
_N�_;h9oaphoric aiid (C H ) NCON"PO(OH)2 (IV). There are 11
Card 2/3 references, 11 of' whiog 24 Soviet.
SOV/ 79-28-6-36163
The Diphenylamide of Trichlorophosphazooarbonio Acid and Its Derivatives
ASSOCIATION: Dnepropetrovskiy metallurgichookiy institut
(I)nepropetrovsk'Metallurgioal Institute)
SUBMITTED: March 5, 1957
1. Phosphoric acids--.,Synthesis 2. Urea--Chemical reacticna
Card 3/3
Kirconov, A. V., Porkitch, G. I* ~009-29-7-AJ6/64
TITLE: Trichloriao 'Dhosphazoac.,,,la of the Arn-matic Scriet. (Tri-
khloricofoofs.-.zoatsily -romstich6:ikogo ryadn)
d
Zhurnal obshchey khi-nii, 195q, Vol, 'M, Nr 7, Pp. 1887-16"
( Tj F's R )
Ali-,,TRACT: Rec,~ntly trichloro obt-'4ned. accord'~ng to
the reactions (1), (2) nnd (3). It wt~s of import;.rce to the
authors to find out rhether the reaction (3)
RCONIIPOCl2 + Pr'l5 -> POCI 3 + wan of goner-il
character or whether it holds only for carboxylic cells with
a clearly eloctronegative chnracter. Itt=cd out that thil
reaction (3) iv of general character for acids of the aronttic
series. The authors obtained trichlorophosphazoncylz of
type RC01 NPOC1 in almost quantitative yielis, in which
R is of the electronegative chr'.ranter junt mentioned (Table 1).
This reaction tnkes place considernbly more slowly nnd at
higher temperature than (1), and it reminded the nuthorn of
Card 1/2 the reaction of phosphorus-pentachloride rith the X,11-dinlkyl-
Trichlorisophoophazoacyls of the Axomatic Series SCV/79-28-7-36/64
amides of carboxylic acids (Ref 5). The t rich loroitionhos T hazo-
acyls of the aromatic aeries are liquid and low meliing cryct'al-
line products and cleave-off POCl 3 on heatine unler the formll-
tion of nitriles according to the scheme:
RCCI NFLIC12 > POCI + RCN (4). They are stable in t.,o
absence of humidity and hn be well ttored in clo!~ed containrrs
at room temperature. Some trichlorophosphazoacyls and di-
chloranhydriden of acylamidophosphoric acids nit well as the
correaponaing acylamidophonphoric acids, which mere aynthe7ized
by the authors and had bel~,n unknown before, oerved sis initial
products. There nre 2 tablen and 7 references, 6 of -;-h1ch
are Soviet.
innti4tut organichc::!,oy 1-himii nunk T11'rainskoy ')MR
(Institute of Organic Chenistryj AS UkrSSR)
SUBMITTED: May 10, 1957
1. Cyclic eampounds--Synthesis 2. Cyclic compounds-Properties
3. Acids-Chemical reactions
Card 212
a 131P 1; OR S Firnanovp ~.. 11, , Matvey(~Pko,
TJTL*~,: Histriaroxyphosphtizo 11oilfonon ind Tetrnnryl Fnter,- o1 the.
.Aj1famI4cb1!-ho!.-nhoric ',011 1
tetrtiarilovyye efiry klaloty)
i ~'A T CID I CA L: Zhurnal obrihph,~.y HJnil, 11)r.R, llo-, 28, :1l- 7, PT 180--V~C!
A!1:;T;1ACT: Only the hie htt!,.P-to
been known of al! vin (torivativrn of
ncid. Ma)itlwr t),.%: ~--,O.`onev nor the ot~ter,
of 00 qu1fw.,,ideh!!-,hosphnrJc h., v.2 been doecribed In
reactc turbulently
with phiniulatec, In dry nt.-.te .-ve.,n to cavbonization. 'In di-
001red k!tz;1lu the r,t,.etion tnke2 vInQt.- wich -.,L'C viiietly under
tv,- formation of the corre:!-onding bi:--triaroxy;,~oupha%o sul-
fonev (1) according to thts !!,-h-?n#!
0 + 614,lOAr --> :,r) 11 0.;,r
2 61NCI (TT).
Th-~! forzatJon of (1) to the schere (IV),
'Urd 1/3 1.%!.) riccording to the fo.-wation c,*' ths- triurox.,.- or trialk-
17
Biptriuroxyphosphazo .;tjlfoner and Tetroaryl Fit-rs o!' tire
phosphoric Acid
or-fphosoh-t-to vulfom.- n1kylit (!,-f ho,.-t-vor, the ri-tictim iTI)
~Y.np Much !,ore difficult than tho!t of (IV) Kith (T) Areptiir
mall imruritl(in o!' the inittal prod,i,!t-_! exprtpd U Strong In-
fl;ienoe or the 'purity of 0'1.- flnil proluetr, _~o thtit for each
Oulfont, (1) GP(!ci?41 conditionri of -synth rift and v Ificatior
weve reqvired. ~~ul Funvv o" t~e type ;r,, N= NO;, V rhc-ro
0-, M- (InA r-"'H ".H (vi, V11, VIII), .nd
'VS 3 h 4 1
9-C10H 7(iX and X), p-1'1(;6!14 (XI) and were syn-
thesized accordinp, to scheme (TY1. Th.~ etruwturp, of these
nPittrR1 compotinis ~7ort, dt!termin-d by merwi of
dttta Gnd conveigionj; tlje--,r were obtrilned in pure et:~te ir-
rpite of their high moleculpr wiight 1.71'-10E' !". nn th-ir
boiling vith alcohol of diluted ilkall liquor the caponifi-
ct4tion according to the =cntion:,d nchcm.-. t.,Aos- rlnco ,(,itnin
2o-,Io minuteal thin the tetraaryle:-~terp of the siL1f.nmidcb.,,_-
phosilhoric acid (XTV) o" the tvvp 1!C 1*0
obtained, rhere Ar-C6H 5 ( Yv 0 m v P_.CH C ivi, !,;Tr
and XVITI), a- Find 'k-C H (XIX 1110 XX:1 'And
10 7
Card 2/5 P-NO C 11 (XXTI). They are fine-crysttil line proAr.**t111' they
1? 6 4
,;!)V '79 -)B
Bintrisroxyphosphazo .",ulfones and Tetroaryl ,-;stern of the
phosphoric Acid
melt tinder decomponition, thty nre not -oluble in g!-.t,~r, i--vt
art, ealublp in acetone, tilcohol t-.)l diox.-ine. There ,-.re 4
reforenceat 3 of whioh are noviet.
ASSOCIATION: Dn~.,propetrovskly metallurgicheakiy inctittit
(Dnepropetrovsk Uetallurgical Institute)
SUBRITTTED: March 5, 1957
1. Bistriaroxyphosphazo sulfones-Chemical properties
2. Sulfamideblophosphoric acid eaters-4hemical reactions
Card 3/3
A1JT'1ORS: Kireanov, A. V., Derkach, 0. 1. SOV/71-2b-8-51/66
TITLE: Triaroxyisophoo,.'tioazoocy3gcf the Aromatic Series (Triarokaiizo-
foefazoatsily aronaticheskogo ryada)
PERIODICAL: Zhurnal obelichey khimii, 1958, Vol. 28, Hr 0,
pp. 2247 - 2252 (USSR)
ABSTRACT: Until now only five triaroxyisophosphoazoacyle of the type
RC(ORQ - NPO(ORQ,,have been synthesized according to
-
+311aOR' --+ 3NaCl+RC(ORQ-NPO(ORQ
the reaction RCC1 "UPOCI
2
2
Reaction I, with the notation R and RO). On1j, one of theoe
compound 13 is crystalline. On the basis of the few facts known
the reaction (1) may be considered a ceneral reaction, or a
conception of the general properties of tYe triaroxyiao-
phosphcazO compounds may be formed. In the previous paper
the authorsworked out a general method for synthesizing
the trichloroisophosphoazoacyle of the aromatic series (Ref 3),
which offered the possibility to determinethe limits within
which the reaction might be used in ret-ard to the triaroxyiso-
phosphoazoacyls. It was found that this reaction can be used
Card 1/3 in all cases for the aromatic series. 22 triaroxyisophospho-
Triaroxyisol;hosphoazoacyle of the Aromatic Series SOV/79-28-8-51/66
azoacyle and 1-trimethoxyisophosphoazoacyl were obtained
in good yield (see the experimental section and table 1).
The properties of these compounds differed sharply from
those of their isowerio triaroxyphosphoazoacyis (Ref 4), as did
those of the triaroxyisophosplioazoacyle from the properties
of the trichloroacetic acid aeries (Refs 1,2). The triaroxy-
isophosphoazoacyls of the aromatic series are crystals of low
melting point and which can be distilled in a hik;h vactium
without decomposition. With heatine under atmospheric
pressure or at reduced vacuum they carbonize gradually, and
the foxiation of triarylphosphates does not occur (this is
a difference from the isomeric triaroxyphosi.lioazoacyle). This
shows that the reaction
ArC(OH) ~IIHPONR) 2 heat ) Or(IOR) doe3 not occur. The tri-
aroxyisophosphoazoacyle of the aLuatic series do not hydrolyse
in boiling water and they saponify easily and quantitatively
only by boiling aqueous alkali alcohol solutiois acco~edinj;
to diagr-w 01)(sve table 2). There are 2 t4bles and 7 refer-
Card 2/3 ences, Ihich are Soviet.
Triaroxyisophosphoazoacyls of the Aromatio Series SOV/71'-~-28-8-51/69,
ASSOCIATION: Inatitut organicheskoy khimii Akademii nauk USSR (Institute
of Orgranio Chemistry AS UkrSSR)
SUB14ITTED: June 5, 1957
Card 3/3
KIRSANOV.--&V.; ZWWTA, I.N.
Reaction of phosphorus pentichloride with phosphoric acid saidese
Zhuroob.khim, 28 no,9:247&2484 s 158. (MIRA l1tll)
1. Institut organlohookoy khimil AN USSR.
(Phosphorus chlorides) (Amides)
1UTHORSS Kirsanov, A. V.9 Derkach, G. I.
r~ -
SOV/79-29-2-52/7'-'
TITM C-Aroxy-P,P-dimetboxyisophosphazoacyls and idixed Triaroxyisophou.-
phazoacyle (C-Arokei-P,P-dimetokaiizofoafazoatoily i emenhaWye
triarokeiizofosfazoataill)
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 2, pp 600-605 (USSR)
ABSTRACTs In the preceding paper (Ref 1) the authors synthesized C-chloro-P,
P-dimethoxyisophomphazoacyls and C-chloro-P,P-diaroxyisophosphazo-
acyle (I) according to the scheme
RCONHPO(OR1)2 + PC15 POC13 + HC1 + RCCI-=NPO(ORI) 2- (1)
The problem was whether the C-aroxy-P,P-dimethoxyi:ofho;pbazoacyle
and the mixed triaroxyisophosphazoacyls of the typ II , which
have hitherto been unknown, may be obtained by aroxylation
of these compounds (1) according to the acheme
RCCl= NPO(OR')2+R"ONA ) NaCl+RC(OR-')~NPO(OR1) (n)
Other syntheses are connected with great difficulties, Synthesj3(11)
Card 112 takes place without difficulties. In mixing equivalent amounts of
SOV/79-29-2-52/71
C-Aroxy-P,P-dimethoxyiaophosphazoacyls and Mixed Triarcxyisophosphazoal~Yls
n-chlorophenolate and C-chloro-P,P-dimethoxy13ophosphazoacyls in
benzene solution the synthesis takes place under 8 strong develop-
meat of heat within 5-10 minutes, in the case of other derivatives
only within 2-3 hours- All mixed triar,.)xyisophosphazoacyls are ob-
tained in crystal-line fo--& after the distillation of the solvent.
The C-aroxy-P,P-dimethoxyisophosphazoa:.yis form first as oils,
which soon adopt a crystalline shape,, Compounds (II) do not hydro-
lyze with water if they are boiled, they hydrolyze difficultly in
boiling,alkal.i lye and easily in aqueous alcoholi,: sclutions of
alkali Scheme 3). Some of the initial compounds were synthesized
anew according to scheme 1 described abo7e~ The mixed triar3xyino-
phosphazoacyle are no insecticides~ In this respect C-n-nitro-
phenox,y-P,P-dimethoxyisophosphazobAntcyI is very active,- There are
3 Soviet references.
ASSOCIATION: Institut organicheskoy khim-IJ Akademii nauk Ukrainskoy 33R
(Inatituf,e of Organic Chemistry of the Academy of Sciences, UkrSSR)
SUIMITTED% December 16, 1957
Card 212
5 (3)
AUTHORS: Kiraanov, A. V., Moloonova, V. P. SOV/79-29-3-53/61
TITLE: Dimethyl Amides of the Alkoxy-dichloro Acetic Acids (Dimetil-
amidy alkoksidikhlorukausnykh kislot)
PERIODICAL: Zhurnal obshchey khimii, 1959, Vol 29, Nr 3, PP 1000-1005 (USSR)
kBSTRACT: Phosphorus pentachloride acts upon the aliphatic esters of the
oxamic acid under formation of the amides of the alkoxy-di-
chloro acetic acids (Ref 1):
NH2COCOOR + PC1 5 ~"'POC13 + NH2COCCl2OR (1), the reaction is
always accompanied by the formation of the trichloro-phosphazo-
alkoxy-dichloro acetyla according to scheme (!I) (Ref 2). In
the case of the dimethyl oxaminates the reaction cannot be car-
ried out according to acheme'(11) so that only the formation of
the dimothyl amides of the alkoxy-dichloro acetic acids accord-
ing to the scheme (CH 02 NCOCOOR t PCI 5-P- POC13+ (CH 3)2NCOCC12OR
(III) is bound to occur. It was found that the reaction (111)
proceeds easily and with an alnost quantitative yield in the
case of the application of the methyl-, ethyl-, n-butyl, and
isobutyl ester of the-dimethyloxamic acid. The phenyl-ester
Card 1/3 of the dimethyloxamic acid cannot react according to scheme(II)
Dirnethyl Amides of the Alkoxy-dichloro Acetic Acids
S07/79-29-3-53/61
so that it is impossible to obtain the dimethyl amide of the
phenoxy-dichloro acetic acid according to scheme (III). The
dimethyl amides of the alkoxy-dichloro acetic acid and the di-
methyl amide of the phenoxy-dich3oro acetic acid are liquids of
pleasant smell, soluble in acetone, M 4' benzene, scarcely
soluble in ether and petroleum ether. They hydrolyze at rcom
temperature slowly with water, moro quickly in the case of
heating. The chlorine atoms in this compound are very mobile
and easily to be substituted. The acid chloride of the dimethyl-
oxamic acid was obtained b~! the thermal dissociation of the di-
methyl amides of the alkoxy-dichloro acetic acids. The aromatic
eaters of the dimethyloxami.c acid were obtained by the reaction
of the sodium arylates with the a.-id chloride of the dimethyl-
oxamic acid or by the action of the phenols upon the dimethyl
amides of the alkoxy-dichloro acetic acids. There are I table
and 5 references, 3 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimli Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences,
Card 2/3 Ukrainskaya SSR)
Dimethyl Amides of the Alkoxy-dichloro Acetic Acids
SUBMITTED: January 23, 1950
SOY/79-29-3-53/61
Card 3/3
5(3)
AUTHCWs Levohenko, YO. 3.t Sheynkmant 1. E.t MY/79-29-5-W75
Kirsanov, Av V.
TITLE& PrePILMUOnr)f Phosphorus-Diiodide and -Triiodide (Poluoheniye
dvukhyodistogo i trekhyodistogo foafora)
PERIODICALs Zhurnal obahohey khimii, 19599 Vol 29, Nr 5, pp 1474-1477 (U33R)
ABSTRAM In -the work under review the authors devised a harmless and - as
to preparaticn - convenient method for the production of phosphorus
diiodide and at tbe same time a method for the pr9duction and
purifioatioL of phosphorus triiodide without use of white phosphorus
and carbon d.sulfide. After numerous experiments it was found that
phosphorus e..iodide and phosphorus triiodide can be obtained in
absolutely I tre form lireatly from iodine and red phosphorus with
subsequent tryaWlization from suitable solvents. The reaction
may be carr.ed out by fusing iodine and phosphorus orlWbcdMgaf iodine
and pbxoxm In solvents applicable to crystallization. Butyl. iodide
and bromide, dichloro ethane, ethyl iodide and other alkyl- and
alkene halcgens can be used for the crystallization of phosphorus
diiodide. (aloro benzene is the most suitable one. The phosphorus
iodide obtiined represents rather large, orange, longish la-In with
Card 1/2 a melting point of 126-1~70. Higher quantities of this preparation
Preparation of Phosphorus-Dtiodide and -Triiodide WV/79-29-5-14/75
can be prepared vithout difficulties. Carbon tetrachloride,
chloroform, butyl iodide can be used for the reorystallization of
phosphorus -triiodide, but most suitable is diohloro-othans.
Phosphorus triiodide is obtained in the form of rather large brilllm4
dark-red crystals with a melting point of 60-610. There are
5 references, 2 of which are Soviet.
ASSMATIONs Institut organicheakoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences,
Ukrainian SSR)
SUMUTTEDs May 61 1958
Card 2/2
5(3) SOT/79-29-5-59/75
AUTHORS: Kirsanovp As V*p Moloonova, V. P.
TITLE: Orthoesters of Oxaminio Acids (Ortoefiry oksaminovykh kislot)
PERIODICALi Zhurnal obehohey khiciip 1959, Vol 29, Yr 5, PP 1684-1687(USSR)
I
ABSTRACT: Amides and dimethyl amides of alkoxydiaroxy acetic :Oid (ortho-
eaters of oxaminio and dimethyl oxaminio acid) NE C C(OR)(OAr)
2 2
and (CH 3)2ffCOC(OR)(OAr)2 were represented by the reaction of
sodium arylates with amides and dimethyl amides of alkoxy
dichloro-acetio acid. Amides with the following alkyl residue
R and aryl radical Ar were synthesized:
R Ar
CH3 CH3
CH3 C6H5
C295 C6H5
C2H5 P-K02C6H 4
n-C499 C6H5
iao-C4H9 C6H5
Card 1/2 and the following diamides:
Orthoesters of Oxaminic Acids SOY/79-29-5-59/75
R Ar
CH3 C6H5
CH3 P-HO2C6H4
C2H5 C6H5
n-C4H9 C6H5
iso-C4H9 C6H5
Reaction temperature* reaction durationg yield v, melting tem-
peraturot formu,la, nitrogen content found and eolubility in
different organic solvents are given in a table. There are
I table and 3 references, 2 of which are Soviet.
ASSOCIATION: Inatitut organicheakoy khiaii Akademii. nauk Ukrainskoy SSR
(Institute of Organic Chemiatry of the Academy of Scienceng
Ukrainskaya SSR)
SUBMITTED: March 31, 1958
Card 2/2
50) SOT/79-29-5-60/75
AUTHORS; Zhmurova# 1. H., 1irfian0Vj__A&_JL-_
C___'
TITLE: Extension of the Range of Applicability of the Phosphazo
Reaction (Rasehireniye granite primeneniya foofazoreaktaii)
PERIODICAL: Zhurnal obahchey khimiif 1959P Vol 29, Or 5, pp 1687-1694 (USSR)
ABSTRACT: By the action of phosphorus pentachloride on triaryl phosphits
one obtains triaroxy phosphorus dichlorides. Not only phos-
phorus pentaohloride but also pentaphenoxy phosphorus and Ari-
phenoxy phosphorus dichloride may be utilized as phosphorus
containing components for phosphazo reactions. Triphenoxy
phosphazo aryls are obtained by the xsaollon of.tbe above-
mentioned compounds with aromatic azines. Production and
properties of the following compound& are given* Triphenoxy
phosphorus d1ohloride, pentaphonoxy phosphorus, triphenoxy
phospha1 0 phenyl, triphenoxy phosphaso nitrophenyle
ArN.P(OC 6H5)3 with the aryl radicals: 4-10 2 C6H 4'
294-(NO 2)2C6R3' 314-(N0 2)2C6H3' NO2 , 2,4,6-(xo 2)3 C6H2
N
(Table 1)9 triphenoxy phosphazoacyls AcHwP(OC6R 5)3 with the
Card 1/2 acyl radicals: C 6a5so 21 302 [H-P(OC6H 03121 (C6H 50) 2POO
SOV/79-29-5-60/75
Extension of the Range of Applicability of the Phoophazo Reaction
(C6H5O)2PS (Table 2). Diphenyl ether of aryl amido phosphoric
acids (C6H50)2 POXHAr with the aryl radicals: C6H,9 4-HO2C6H4'
2~4-(NO2)2CO39 394-(N02)2 C6H39 No 2 (N (Table 3).
There are 3 tables an4 19 references, 10 of which are Soviet.
ASSOCIATION., Institut organicbeekoy khimii Akadecii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Scienceep
Ukrainskaya SSR)
SUBMITTED: April 5, 1958
Card 2/2
50)
AUTHORS: Kireanovt A. V.0 lirsanova, N. A. SOV/79-29-6-7/72
--------
-
TITLE: --------------
Derivatives of m- and p-Benzene Disulfonic Acid (Proizvodayye
m- i p-benzoldisullfokislot)
PERIODICAL: Zhurnal obahchey khimiig 1959# Vol 29, Nr 6, pp 1802-1813
(USSR)
ABSTRACT: The derivatives of the p-benzene disulfonic acid can be
used as initial products for new high-molecular products.
The simplest derivatives of the p-benzene disulfonic acid
are of particular interest. In the present paper the authors
tried the synthesis of the simplest derivatives of the m-
and p-benzene dieulfonic acid and further that of the
m,mi-diphonyl-oulfone-dioulfonic acid. The methyl and ethyl
eaters of the m- and p-benzene disulfonic acid as well as
of the m,mi-diphenyl-oulfone-disulfonic acid were obtained
by the action of a benzene solution of the corresponding
diobloride on sodium alcoholate solutions which were previ-
ously concentrated by evaporation in the vacuum to syrupy
consistency. When using nearly dry sodium alcoholates the
reaction takes place at the boiling temperature of benzene
Card 1/3 only with a considerable alcohol excess, but it is not
Derivatives of m- and p-Benzene Disulfonic Acid SOV/79-29-6-7/72
possible to separate the dieeters of the benzene disulfonic
acids as they are strongly alkylating agents and therefore
react with the excess alcohol. The reaction thus proceeds
according to the scheme
C6 H4(SO2CI)2 +2ROKa - 2NaC1 + C6H4 (SO 20R)2;
C6H 4(30 20R)2+ ROH ___w ROR +C 6H4 (SO 2OR)SO2OH. At a lower
alcohol quantity the reaction proceeds slowly in the second
step, and it is possible to separate the diester prior to its
alkylation. The methyl and ethyl esters of the m- and p-
benzene disulfonic acid are crystalline, readily melting
compqunds and are iapidly saponifidd when heated in water.
It was shown that the methyl esters of the acids mentioned
have an intermediary position between the methyl esters of
the aryl oulfonio acids and those of the nitroaryl sulfonio
acids as far as their alkylating capability is concerned.
The phosphaso-reaction was carried out for the diamides of
the above-mentioned acids. The following compounds were ob-
tained; m- and p-bia-trichloro-phosphazo-sulfone-phenylene#
tetia-acid chlorides of the m- and p-phenylene-bis-oulfon-
Card 2/3 ami o-phosphoric acid, m- and p-bia-trialkoxy- and bia-tri-
Derivatives of m- and p-Benzene Disulfonio Acid SOV/79-29-6-7/72
phenoxy-phosphazo-oulfone-phenylene and totraestera of the
m- and p-phenylene-ble-oulfonamido-phosphoric acid (5 Tables).
The monoamide-monochloride of the p-benzene-dioulfonic acid
and a number of N-alkylated amides of the m- and p-benzene
disulfonic acid were obtained. There are 5 tables and 17
references, 9 of which are Soviet.
ASSOCIATION: Institut organicheekoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences,
lUkrainstaya SSR)
SUBUITTED: Uay 20, 1958
Card 3/3
AUTHORS: Levobenko# Ye. S., Kirsanov, A. V. SOV/79-29-6-8/72
TITLE: Reaction of Phosphorus Pentachloride With the N-Chloro-
Derivatives of Aryl Sulfamidea (Reaktsiya pyatikhloristogo
foofora a N-khlorproizvodnymi ariloullfamidov)
PERIODICAL: Zhurnal obshohey khimii, 1959, Vol 29, Nr 6, pp 1813-1814
(USSR)
ABSTRACT: Two methods have so far been applied for the synthesis of
the trichloro-phosphazo-compounds: The reaction of phosphorus
pentachloride with acid amides (Ref 1) and the reaction of
phosphorus trichloride with the sodium salts of the chloro
amides of the sulfonic acids (Ref 2). The latter reaction
proceeded according to the scheme
Ar$02NNaCl + PC15---p- NaCl + ArSo2N'PC'3 - It was previously
assumed that the acting force of this reaction would preva-
lently be the tendency of the trivalent phosphorus atom to
pass over into the pentavalent state. It was found, however,
that also phosphorus pentachloride does not only vigorously
reaot with the sodium salts of the H-chloro-amides of the
sulfonio acids, but also with the N,N-dichloro-amides of the
Card 112 sulfonic acids, thus yielding trichloro-phosphazo-compounds
Reaction of Phosphorus Pentachloride With the SOV/79-29-6-8/72
H-Chloro-Derivatives of Aryl Sulfamides
and free chlorine according to the scheme
ArSO 2XNaCl+ PC1 5 NaCl + C12 + ArSO 2N~Pcl Y
LrSO 2NC1 2+ PCl 5---a- 2Cl 2+ ArSO 2 N-PCl 30 This reaction pro.
ceeds readilyp with good yieldep and gives high-purity
trichloro-phosphazo-compounds. Without solvent the reaction
of pho 'sphorus pentachloride with the above-mentioned salts
takes place so abruptly that the reaction products are
completely charred. In carbon tetrachloride the reaction
proceeds normally under heating. The N,N-dichloro-amiden of
the sulfanic acids react slowly with PCI 5 in CCl 4 at room
temperaturep but rapidly when heated. There are 4 Soviet
references.
ASSOCIATION: Institut organicheakoy khimii Lkademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences,
Ukrainakaya SSR)
SUBMITTED: May 27, 1958
Card 2/2
AUTHORS: Derkach, G. I., Kirsanovp A. V.' SOV/79-29-6-9/72
TITLE:' C-Phosphinyl-P,P-Diaroxy-Iso hosphazo-Aroyls (C-Poefinil-
P,P-diarokaiizofoafazoaroily~
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 6, PP 1815-1818
(USSR)
ABSTRACT: The C-ohloro-PgP-diaroxy-isophoaphazo-acyle of the
ArCCl-mNPO(OArl )2 type yield under the influence of water
the diaryl eaters of the acyl-amido-phosphoric acids (Ref 1),
under the inf3uence of sodium alcoholates and sodium arylates
the corresponding eaters (Hof 2). They reactreadily with
ammomia and amines and are an acylating agenta'analoge of
the acid chlorides of the carboxylic acids. It was of intere4
to find out whether this analogy also holds for the reaction
of A. Ye Arbu30v# i.e. whether the above-mentioned acyle
'
also
rea;t wit1h the eaters of the phosphorous acid like the
acid chlorides of the earboxylic acids. This was confirmed
by the experiments. Theoe'aoyle react already at -150 under
considerable heat evolution accor4ing to Arbuzov and yield
Card 1/2 the corresponding C-phosphinyl-P,P-diaroxy-isophosphazo-amyle
C-Phoophinyl-P,P-Diaroxy-Isophosphazo-Aroyle
according to the scheme;
ArCC1-NPO(OAr1) 2 +P(OAlk)RRI
SOV/79-29-6-9/72
- AlkCl +ArC-HPO(OAr' )2 (1)
0PkR'
(1)
only two have a
Among the 9 compounds synthesized
crystalline nature, the remaining ones are dense liquids or
vitreous products. Analytical dati.t appearance, solubility,
and melting points of these compoinds are given in the table.
By shaking with 90 0,6 alcohol they hydrolyze quantitatively
within 4-6 hours yielding the dieiters of the acyl-amido-
phosphoric acids and the correspozding acid eaters of the
phosphorous acid, phosphinic acid or also of the free
diphenyl-phosphinic acid, accordin,- to scheme 2. On the
hydrolysis of the compounds (IV) and (VIII) (Table) it was
possible to separate nearly quantilatively the aiphenyl-
phoephinic acid. There are I table, and 5 references, 3 of
which are Soviet.
ASSOCIATION: Institut organicheskoy khimii Akadev-ii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences,
Ukrainskaya SSR)
SUBMITTED: May 27, 1958
Card 2/2
5 (3)
AUTHORS: Zhmurovaj I. No, Voytsekhovskayaq I. Tu., SOY/79-29-6-67/72
Kirsanovp A. V.
TITLE: Direct AmIdation of Carboxylio Acids (Kepo3redetvennoys
amidirovaniye karbonovykh kielot)
PERIODICAL: Zhurnal obahchey khimii, 1959P Vol 29, Nr 61 pp 2083 - 2088
(USSR)
ABSTRACT: In this investigation the authors attempted to extend the scope
of application of direct amidation of carboxylic acids, under
"softer conditions in a pyriaine solvent" (Ref 3) without ex-
amining the question of amidation under "harder conditions at
higher temperatures". Different amides affect carboxylic acids
quite differently, It is especially unintelligible that several
homologues and analogues of trianilide of the phosphoric acid
do not react with carboxylic acidap when heated in pyridins.
The question was of interest, whether the amides of the mono-
basic phosphoric acids occur in pyridine as an agent of amida-
tion, and whether for amidation under "soft conditions" the
presence of two groups of amides in the molecule is necessary,
in which at least one "free" hydrogen atom, connected with the
Card 1/3 nitrogen atom of the amide group (Ref 2) has to be present.
'Direct Amidation of Carboxylic Acids BOT/79-29-6-67/72
Amides of the type (RO)2P0NH2 and Ar 2PONH2 and their N-subeti-
tuted compounds were selected as samples to be analysed. The
amide and the dimethyl amide of the diphenylphosphinic acid am.
idate the carboxylio acids, when heated in pyridine or dioxane
and are very easily saponified. The amidation capacity of the
amides of the diphenylphosphinic and diphenylthiophosphinic ac-
ids corresponds to thair easiness of saponification i.e. to
their capacity to combine with hydroxyl. The amide, dimethyl-
amide and phenylamide of the diphenylthiophosphinic acid and
the phenylamide of diphenylphosphinic acid do not amidize the
carboxylic acid under the same conditions, and it is difficult
to saponify them. The mechanism of amidation of carboxylic ac-
ids with amide and dimethylamide of the diphenylphosphinic ac-
id differs from the mechanism of amiclation of the carboxylic
acids with amides of the sulphuric acid. Some amidea of the
diphenylphosphinic and diphenylthiophosphinic acid were syn-
theaized. The amidation with the amide of the diphenylphos-
phinic acid, according to the scheme
RCOOH + (C 695)2PONH2 --3,RCONU2 + (C 6H 5)2 POOR
Card 2/3 takes place especially smoothly. In the table amides of both
*Direct 1midation of Carboxylic Aoide 807/79-29-6-67/72
phosphinic acids are listed. There are 1 table and 11 refer-
ences# 2 of which are Soviet.,
p
ASSOCIATION: Institut organicheskoy khimii kkademii nauk Ukrainskoy SSR
(Institute of Organic Chemintry of the Academy of Sciences
of the Ukrainian SSR)
SUBMITTED: May 6, 1958
Card 3/3
5'(3)
AUTHORS: Kirsanov, A. V., Marenets, M. S. SOV/79-29-7-33/83
TITLE: Urethan Phosphoric Eater (Efiry uretanfoafornykh kislot)
PERIODICAL: Zhurnal obehohey khimii, 1959, Vol 29, Nr 7, pp 2256 - 2262
(USSR)
ABSTRACT: Mothylurethan-N-phosphate CH 3OCONHPO(OCH A (Ref 1) which was
recently synthesized by Kirsanov proved to be an active non-
poisonous insecticide preparation for haematherme (further re-
ferred to as X-20-35)- It was of interest to synthesize com-
pounds similar to this preparation and to develop less compli-
cated methods of the synthesis of K-20-35 and its analogues
and to produce them industrially. They succeeded in working
out two now reaction schemes for the synthesis of K-20-35, the
first of which consists of three stages "3 Yield) and the
em ) (
second of two stage;J(80~). LSch e (1 and 2)]. For higher
Iluantities scheme ( ) is suited, for the homologues of E-20-35
scheme M According to scheme (II) a solution of methylureth-
an-11-phosp~ate (K-20-35) in methanol resulted after the second
stage which contained 2 mole of HC1 and 1 mol of methyl chloride
Card 1/2 per 1 mol of X-20-35. After longer standing (more than 3 hours)
Urethan Phosphoric Eater
SOV/79-29-7-33/83
as well as in immediate evaporation of the mothyl chloride the
yield is considerably reduced. AmonC the eaters of trichloro-
phosphazo carbonic acid of the type n0CON.PCl 3hitherto only
the ethyl estor (Refo 3,4) has been known (Scheme III). Accord-
ing to the same scheme the methyl-, isopropyl-, n-propyl-, 'Loo-
butyl- and n.-butyl ester of trichlorophosphazo carbonic acid
were obtained. When these esters are heated, thel decompose
quantitatively according to scheme (IV) (Tabl e 1 . In contrast
to the earlier scheme (V), the acid dichlorides of urethan-N-
phosphoric acids were obtained accordinC; to scheme (VI) in an
almost quantitative yield (experimental part). In table 2 the
acid dichlorides of these acids are given. The temperature of
the thermal cleavage of the above estero into alkyl halides and
acid dichlorides of isocyanate phosphoric acid depends on the
nature of the alkyl. Some of the eaters synthesized proved to be
active insecticides. There are 3 tables and 6 Soviet references.
ASSOCIATION: Institut organicheakoy khimii Akademii nauk Ukrainakoy SSR
(institute of Organic Chemistry of the Ukrainskaya SSR)
SUBMITTED: June 9# 1958
Card 2/2
*K1q'-JA"0V' f\,V.
5 (3)
AUTHORS: Levchenko, Ye. S., Zhmurovat 1. 11.# SOV/79-29-7-34/83
TITLE: Reaction of Phosphorus Pentachloride With Acid Dichlorides and
Diesters of the Aryl Sulphonamidophouphoric Acids (Reaktsiya
pyatikhloristogo foefora 9 dikh1oranj-;idridami i diefirami aril-
oullfonamidofoeforn.ykh kislot)
PERIODICAL: Zhurnal obahchey khimii, 1959, Vol 29, Nr 7, pp 2262 - 2267
(USSR)
ABSTRACT: Xirsanov succeeded in transforming the trichloro phosphazoeul-
phonalkyls and aryls of the type RSO 2N-PC13 into the acid di-
chlorides of the corresponding alkyl- and aryl sulphonamidophos-
phoric acide according to the scheme RSO 2N-PC1 3+H2 0 --4 HCl+
+RSO2NHPOC12 by the action of water or formic acid (Ref 1). It
was of interest to find out whether a reverse transformation
was possible, i.e. whether the corresponding trichlorophosphazo
compounds could be obtained according to the scheme RSO 2 11HPOCIe
Card 1/3 +PCl5 HCl + POCI3 + RSO 2N - PCl 3(1) fron the acid dichlor-
Reaction of Phosphorus Pentachlorido With Acid SOV/79-201-7-34/83
Dichlorides and Diesters of the Aryl Sulphonamidophos-
phoric Acids
idea of aryl sulphonamidophosphoric acids. The experiments
showed that the reaction (1) for the acid dichlorides of o-,
m-j and_p7nitrophonyl sulphonamidophosphoric acids take a place
at 130 350-within 10-15 min in yields of from 47 to 80% as
well as for phenyl eater of the N-(dichlorophosphinyl)-mono-
amide of p-benzene disulphonic acid at 115-1200 within 20-25
min in a yield of 49%. In all cases by-products of unknown na-
ture are formed. Also in the reaction of PC1 5 with the potas-
sium salts of the acid dichlorides of nitrophonyl sulphonamido-
phosphoric acids the same yields wero obtained. In the action
of PCl5 on the acid dichlorides of aryl oulphonamidophosphorio
acids, the molecules of which contain no other substituente in
the aromatic nucleus, no corresponding trichlorophosphazo sul-
phonaryls are formed. In the reaction of n1l 5 with the diphenyl
eaters of the above acids the diphonoxy chlorophosphazosulpho-
naryles irrespective of the nature and the position of the sub-
Card 2/3 atituents, are obtained in the aromatic nucleus of sulphonic
Reaction of Phosphorus Pentachloride With Acid SOV/79-29-7-34/83
Dichlorides and Diesters of the Aryl Sulphonamidophos-
phorio Acids
acid (Scheme 3), The constants, analytical data and the yields
of the diphenoxy chlorophosphazosulphonaryls are tabulated.
There are I table and 7 Soviet references.
ASSOCIATION: Inatitut organicheekoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences of
the Ukrainakaya SSR)
SUBMITTED: June 23# 1958
Card 3/3
KIRWOV, A.V. [Kirsanov, O.V.1; ZHMVLIWA, L*?. (Zhuraviloya, L.P.]
Diethers Of N-diidtOXY- and li-diaro37phosphsnylcarbasinyl..-
phosphouic aaids,' Dop,AN UM no.4:487-489 l6o. (MIRA 13-7)
19 Iu~tltut'orgumIchaskow khimij An USSR. Chlon-korrespondent AN
USSR (for Kireanov).
(Phosphonic aoid)
IURR NOV, A.V. (Kirsanov. O.V.); PIWOROVA. G.I. (Fedorova, H.1-1
Complexes of phosphorus pentachloride with aryl- and st7ryl-
phosphorus tetrachlorides* DapeAH URSR. no.6%801-803 160.
(Ulu 13:7)
1. Inst~tut organicheakoy khimil AN USSR, 2, Chlew-korretpondent
AN USSR (tor Kirsanov).
(Phosphorus chlorides)
XIRSANOV, A.V. [Kirmanov, O.V.1; ZHMVLEVA, L.P. [Zhuraylloya, JA*P*J
1-aryl, 1-benzoyl- and 1.1,dimethyl-4-dichlorphosphinyleasicar-
basides and their derivatives. Dop.AN URSR no.6:804-808 160.
(MIRA 13.7)
1. Institut organichookoy khimii AN USSR. 2. Chlen-korrespondent
AN USSR (for Kireanov).
(Somicarbaxide)
lcill~V, A.V.; ZMUVLIMAg L.P. [2huravllova. L.P.]
0 mom
.Reaction of the dichloranhydride of isocyawtophosphorio sold with
water. lbp.Al UISR UO#72929-931 460, (XIRA 1318)
1. Institut orpulcheskoy khlmil AN USSR. 2. Chleii-korrespondent
AN USSR (for Kirmanov),
(Carbamic acid)
I
A.T (Kilvanov, G.T.1; 710MOTA, G.K. (Yedorova, ILK.]
Complex compowAs of phosphorus pentachloride with o~,OL-dlchloralkyl-
phosphorus t4trachlorideso DDp.Ax URSR no.8:1086-1089 l6o.
O(IRA 13:9)
1. Institut organicheekoy khtmit AN USSR. 2. Chlen-korrompondent
AN USSR (for Kirmanov).
(Phosphorus cholorides)
4
.1-3630 77398
SOV/79-30-1-59/78
AUTHORSt Kirsanov, A. V., Feshchenko, N. 0.
TITLEt Esters of Aminobenzoylamidophosphoric Acids
PERIODICAts Zhurnal obahchey Ichimll, 1960, Vol 30, Nr 1, pp 267-
270 (USSR)
ABSTRAM Esters of aminobenzoylamidophosplioric acids were syn-
thesized according to the following scheme:
NOA114C.ONIfs t~PE~f NOA114CON"PCI3 Ill + 11COOK
NOICS114CON11POCI, Ill NOA114CON11PO(OR)t (11 -' 4-
P&
N1j"1.GONHPO(OR)j.
Dimethyl and diphenyl este:~,s of nitrobenzoylamidophos-
phoric acids were obtained by the previously described
methods (A. V. Kirsanov, I:v. AN SSSR, OKhN, 1954, 646;
A. V. Kirsanov,.R. 0. Maki.ra, ZhOKh, 26, 905, 907,
Card 1/19 1956, and others). The ni;robenzoylamidophosphoric
Esters of Aminobenzoylamidophosphoric AcidE 77398
SOV/79-30-1-59/78
ASSOCIATION:
SUBMITTED:
acids were reduced to the eEters of aminobenzoylamido-
phosphoric acid In an alcohclic solution in the presence
of a platinum catalyst. Yiclds and the properties of
the esters are given In Table l.- In order to character-
ize the above esters, their benzoyl derivatives were
prepared by the Schotten-Baumann reaction (see Table 2).
There are 2 tables; and 3 Soviet references.
Institute of Organic Chemistry, Academy of Sciences,
Ukrainian SSR (Institut organicheskoy khimii Akademii
nauk Ukrainskoy SSR)
January 19, 1959
Card 2/4
Ir
MHORS: Levchanka, Ye. 8.0
TITLE: Acid Chlorides of I-Diabloro-phosphi
Acidel
3/079J60/030/05/31/074
B005/BO16
1-arene-imino-multonic
PBRIODICAL: Zhurnal obahchey khimii, 1960, Vol. 30, No- 5, PP- 1553-1561
TEXT: The authors of the present paper chocked a paper by I. Braun and
K. Weissbaoh (Ref. 5) for its correctness. The Investigations revealed
that all statements of theme authors regarding the reaction of phosphorus
pentachlorido with *thylamides of sulfonic acids were wrong. It was proved
xperimentally that in this reaction mainly PCI is separated. Therefore,
revalently a chlorination occurs whereas the aathore of Ref- 5 state that
;
an oxygen atom of the sulfo group is replaced by chlorine with POC13 being
separated. The principal products of the reactions of PC1 with the
ethylamidon of n-butane- and cyclohexano-oulfonio acid arz liquids which
do not form crystals and are distillable in vaouo with slight decoMpositio.-6
In contradiction with the statements of Ref. 5, the acid chlorides of
N-othyl-butane-imino-sulfanic acid, or X-ethyl-eyolohexane-imino-sulfonic
Card 1/3
Acid Chlorides of I-Dioblora-phosphinyl-arene- 8/079/60/030/05/31/074
imino-sulfoule Acids B005/BO16
acid, respectively, could not be isolated from these liquids. When treating
the diacid chlorides of aryl-oulfonasido-phosphoric acids (I) with P01
acid chlorides of N-diohloro-pho "Phinyl-arene-imino-sulfonic acids (113
or trichloro-phosphaso-oulfonaryin (III) are formed. If the aryl radical
of the diaoid chloride used as initial product contains olectron*gative
:ubstituente, the compounds (III) resulto Ifthe &ryl radical contains no
lectronegative substituents, th oo;pound3 II) are obtainedCin good yields.
Table I shows 9 compounds of thi: ty 0 (11 XG0450(-NP0012) 1) which
were prepared in this way. Yields, appearance, melting pointt empirical
formula, and chlorine content are given for each compound. The solubilities
of the compounds (11) in the common organic solvents are presented. The
compounds (II) are typical &old ohlorld**, but show no acid properties
contrary to the diacid chlorides (1). On the action of water at room
temperature they are slowly hydrolysed. They react readily with alcohols,
phenols, ammonia, aminest alcoholatoo, phenolates, and other compounds with
active hydrogen. Under the influence of phenolates the aryl esters of
N-diaroxy-phomphinyl-arene-imino-oulfonio acids (IV) result in good yield.
Table 2 gives 9 compounds of type (IV) which were obtained from the oom-
pounds (II) presented in Table 1, 14z addltAon to the respeotive e-ta iriven
Card 2/3
Acid Chlorides of N-Diohloro-phosphinyl-grone- 3/079/60/030/05/31/074
imino-oulfonio Acids B005/BO16
in Table 1, this table contains data an the solubility in 6 organic sol-
vents. The authors furthex investigated the direction of reactions of the
type XBO 2NHPOZ2+ PC15 0' ISO(-x?0Z 2)C1 or X$02-NPZ2C' in dependence on
the character of the groups X and Z. The results are summarized in Table 3.
The investigations are thoroughly discussed. In an experimental part all
procedures carried out are described in detail. There are 3 tables and
7 references: 2 Soviet and 5 German.
ASSOCIATION: Institut organichaskoy khimil Akadenii nauk Ukrainskoy SSR
(Instltutl of Orsnia Chemistry of the Academy of Sciences,
Ukrainakays, SS
SUBMITTED: May 7# 1959
Card 3/3
MCHMO, Te*So; SMXMN, I.I.; ZIRSANDV, A.T.
Phanylamides of 9-diantlidophosphinylareniminosulfouic acidas
Zbur.ob.kblm. 30 no.6:1941-1946 Js '6o.
(MIRA 13: 6)
1. Institut organicheskoy khimil Almdemll nauk Ukrainskoy SSR,
(Asides) (Salfonic acids)
LITCEINKO, Te.S.; 13RKAGE, N.Ta.; KIRSAMV. A.T.
Chlorides of S-iu7lsulforglareniminosulfoule acids. Zbur.ob.
khim. 30 no.6tl971-1975 Je 160. (MIR& 13:6)
1, lustitut orgautchaskoy khimii Akademii nauk Ukrainskoy
SSR,
(Salfonic acids) (Chlorides)
8/079J60/030/06/07/009
B002/BO16
AUTHORSs Loychonkop To. Be, Pivenip Yho To, Xireanoyp As Vo
TITLEs Alkylationlof Phosphorus Diiodido
PUIODICALs Zhurnal obehahey Wally 1960t V01- 309 Not 6t PP* 1976-1981
TEXTs In the present paper the alkylation of PI 3 and especially of P21 4
by means of alkyl halides is investigated. The phosphorus iodides are
trongly nucloophilio compounds (the addition of an electronophilio group
:
uch as alkyl halides takes place readily in this case according to '
A. To. Arbuzov (Refs 3) and other scientists). The reaction mechanism in
explained* The reactions were carried out with benzyl iodide and bensyl
chloride, further with CR3-1 q 95-P n'-03"7-p n.-C 4R9-, and iao-CE,,-
iodide* The mixture of P21 4 + bensyl iodide was heated up to 110-11501
the "action at this temperature was exothermal. An intermediate complex
was formed firstj which was converted to tribenzyl phos-hine, yield 9%,
under the action of alkali and reducers# but not on moderate heating In
Card 1/3
Alkylation of Phosphorus Diiodide 5/07 60/030/06/07/009
3002Y301 6
vacuo. The reaction~also proceeds in solvents with ohlorobenzene being
most suitablee The reaction was further shown to be possible also with
red phosphorus + iodine + bensyl. Iodide and red phosphorus + bansyl
iodide$ P 21 4' + I zuBt,be added in this connection in catalytic quantity
only* It was concluded therefrom that the reaction presumably takes place
via P21 4 being formed* PI 3+ bensyl iodide gave only a small yield of
tribensyl phosphinic oxide and dibensyl phosphinic acid* The alkylation
proceeds via the formation.of P I which was confirmed by the fact that
2 4
the yield was considerably increased in the letter reaction by further
phosphorus addition, p-bonsyl chloro-iodide reacted like bonsyl iodid*9
p-nitrobanzyl iodide-rapidly tormed.zesinous products. It was not possible
to isolate mono and dibensyl phosphinio acids from the reaction P21 4 +
+ bensyl iodidet. since the partly a4ylated products are further alkylat-
ad much more easily than P21 4 itself*' The reaction P214 + alkyl iodides
took place only in a sealed tube at 200-22000. After hydrolysis the
oxides of the corresponding trialkyl phosphines were formed, The proportion
of the compounds thus obtained correspond with data from publications
Oard 20
KIRSANOT, A,V.; SHOEDL, V.I.
-------
Diesters of thloacylamidophosphoric acids. Zhur. ob. khime 30
no-9:3031-3037 8 160. (MIRA 13:9)
1. Institut organicheekoy khimii AkademH nuak Ukrainstoy 3SR9
(Phosphoric acid)
.-KIRSAMY, A.Y. -, ZHURAVLWA, L.P.
Diestere of N-dialkoxy- and 9-diaroxyphospbpnylcarbaminylphosphonic
acids. Shur* ob, khim, 30 no.9:3038-3041 5 160. (Knu 13:9)
1. Institut organichookoy khimii Akademii nauk Ukrainskoy SSR.
(Phosphonic acid)
7ZHC - , N*G.; ~,]~~IOV, A.V.
---I
Phosphours Iodides. Zhur. ob. khim. 30 n0-9:3041-3043 3 160.
(MIRA 13:9)
1, Institut organicheskor khimli Akademii nauk Ulcrainakoy SSR.
(Phosphorus iodide)
S/079J60/030/009/011/015
BOOI/BO64
AUTHORS: Zhmurova, I. N., Kirsanov, A. V.
TITLE,. Trichloro-phoapha z0 ~;~Yls
PERIODICAL: Zhurnal obahchey khimii, 1960, Vol. 30, No- 9, RP-3044-3054
TEXT: In continuation of papers of Refs* 1-4 the authors studied the re-
action of phosphorus pentachloride with a series of aromatic amines and
some derivatives of aryl amido phosphoric acids. Trichloro-phosphazo acyle
are obtained almost quantitatively on the action of PCI 5 on acid amides
(Ref. 1). On the reaction of aromatic amines or their hydrochloric salts
11 ith Pal in boiling carbon tetrachloride compounds are obtained in good
xields, hich, in their composition, precisely correspond to chloro-phos
phazo aryls (Table 1). ArNH 2 + Pal5 b 2HC1 + ArN - Pal 3 (1)
ArNE3Cl + PC15~--+ 3HCl + ArN - PCl3 (11)
Amines with basicity Kbas 0 10-9 - 1013 give rise to trichloro-phosphazo
aryls in the form of dimers, while low-basicity amines yield such in the
form of monomers. Dimers of trichloro-phosphazo aryls obtained from amines
Card 1/3
Trichloro-phosphazo Aryls S/079/60/030/009/011/015
B001/B064
with Kbas ' 10-9 - 10-10 0 ar6 decomposed, on boiling, in benzene solutions,
and not in monomers, whereas dimers from low-basicity amines are partly
or wholly decomposed into monomers. Monomers of trichloro-phosphazo aryls
resulting from aminse with basi6fty K bas w 10-10 - 10-13, could be obtain-
ed in benzene solution only. When their solutions are evaporated, t1le mono-
mers are converted into the respectiv; dimerse Trichloro-phosphazo aryls
from aminee, with Kbas . 10-14 - 10-1 resemble the trichloro-phosphazo
acyla as to their physical and chemical properties. Again with respect to
these properties, the dimers of trichloro-phosphazo aryls differ sharply
from trichloro-phosphazo acyle and apparently possess a cyclic "benzoid
structure". Dimers of trichloro-phoaphazo aryls likewise result on the
action of PC1 on a series of aryl amido phosphoric acids. The dimers
of trichloro-?hogphazo aryl,) derive their importance from the fact that
thdy are also formed by the'reactioL of phosphorus pentachloride with
various derivatives of aryl amido phosphoric acids (Table 2). There are
2 tables and 13 references: I Soviet, 6 US, 1 German, 3 British, and
2 French.
Card 2/3
Trichloro-phosphazo Aryls S/079/60/030/009/011/015
13001/B064
ASSOCIATION: Institut organicheskoy khimii Akademii nauk Ukrainskoy
38H I
(Institute of Organic Chemistry of the Academy of Sciences
of the Ukrainskaya 35R)
SUBMITTED: July 31, 1959
Card 3/3
KIRSANOV, A.V.; FESHCHENK , N.G,
Azo dyes based on dimthvl esters of amin phonylmilfonylamidophosphoric
acids. Zhur.ob.kh4m. 30 no.lDs3389-3392 0 161. (KMA 1/+:4)
I* Institut organicheskoy Ichim" Akademii nauk Ukrainakoy SSR.
(Phoophoramidic acid) (Aso dyes)
DERKACH, G.I.; SHOKOL, V.A.I.XIRSANOV, A.V.
Diesters of acylamidophosphoric acids* Zhursob.khim. 30 noolOt
3393-3397 0 1'61, (MIRA 344)
1. Institut organicheakoy Ichimil Akademii nauk UkrairAskoy SSR,
(Phosphoramidic acid)
8h881
0 5, 1110, 8/07 60/030/010/023/030
BOOIYB066
AUTHORS: Darkach. G. I. and Kirsanov, A. V.
TITLE: Polymerization of N-Diaroxy-phosphinyl Arene Amidine
PERIODICAL: Zhurnal obahchey khimii, 1960, Vol- 30, No. 10,
pp. 3397 - 3401
TEXT: The amidines ArC1-"PO(OArt)21NH2 synthesized by the authors in a
previous work are quickly and quantitatively polymerized by strong
mineral acide to give colorless, crystalline products without basic
properties (Table 1). According to their ultimate analysis and molecular
weight, they are trimers of the N-diaroxy-phosphinyl arene amidines.'
Polymerization takes place readily and with small quantities of strong
mineral acida, as well as with formic and acetic acid; benzoic acid is
ineffective. If the amidine hydrochlorides are exposed to air, they are
quantitatively converted into trimers after some days, which is not the
case in dry air, not even after several months. Polymerization proceeds
smoothly when boiling their salts in 96% ethanol and dissolving them in
Card 1/3
84881
Polymerization of N-Diaroxy-phosphinyl S/079J60/030/010/023/030
Arene Amidine Booi/Bo66
concentrated sulfuric acid# The trimers of N-diaroxy-phosphinyl arens
amidines greatly differ in their properties from the initial monomers:
They melt at considerably higher temperatures, are insoluble in most
organic solvents (contrary to the monomers), and are not changed when
treated with dilute acids and alkali lyes, not even by short boiling.
Polymerization is usually caused by the unsaturated state of the mole-
cule. Thus, a double bond causing trimerization is bound to exist in the X
molecules of N-diaroxy-phosphinyl arene amidines, i.e., between the
carbon atom and one of the nitrogen atomo. It can thus be illustrated
only by -the two tautomeric forms
NH - H.. N - H..
ArC 0 ArC 0
N - P(OW )2 KH --F OAV )2
M
(II)
For this work,some N-diaroxy-phosphinyl arene amidines hitherto unknown
were synthesized by the previous method (Table 2). There are 2 tables
Card .2/3
DERKACH, G.I.; DREGVALI. I?jj XIMANOV, A.V, .
. I - I
Trichloraphosphas~-~-arylmtlforqliminobenzoy3.9. ZJn=.ob.JrhJa 30
noelOt3402-3407 ll.i 161. (KEPA 24 W
1. Inotitut organichookoy khImli AN Ukraiwkoy ssR.
(Phosphazo, compounds)
87532
S/079/60/030/012/016/027
BOOI/BO64
AUTHORSt Fedorova, G. K. and Kirsanov, L IV.
TITLE: Reaction of Phosphorus Pentachloride With Unsaturated Hydro..
carbons
PERIODICAL: Zhurnal obshchey khimii, 1960, Vol. 30, No, 12, PP-4044-4048
TEM No compound of the RCHClCH 2PC1 4* PC15and RCHClCH2PC14 types had
hitherto been obtained in the pure state. It is hardly believable that in
the hydrolysis of such compounds or under the action of SO 2 upon them,
under milder conditions, a quantitative separation of HCl should take place
only under the formation of unsaturated phosphinic acids or their acid
dichlorides, and not under the formation of the correspondingA -chloro
phosphinic acids or their acid dichlorides. It may be assumed that the
reaction of PC1 5 suggested by E. Bergmann and A. Bondi (Ref.4) with un-
saturated hydrocarbons may proceed in a different way, i.e., without
formation of A-chloro phosphinic acid derivatives by the scheme
Card 1/3
87532
Reaction of Phosphorus Pentachloride With S/079/60/030/012/0!6/027
Unsaturated Hydrocarbons BOOI/BO64
6
RCH-CH + PCI o[(RCHCH RCI 4 [RCH-CHPCI+] tPC
2 2PC14 3
->RCH- CHPC1 PC1- It was the aim of this study to obtain the
3 6 -
immediate reaction products of PCI 5 with unsaturated hydrocarbons and to
identify them. PC1 5 which reacts readily with styrene, was the initial
product. A crystalline complex C H CH-CHPC1 +. PCl- formed at 0 0C in the
6 5 3 6
course of six hours under the formation of 1 mole HC1. Thus, it may be
concluded that in this case the intermediate product of the
1rCHClCH 2PCI4-PC1 5(Ref-7) does either not form at all or is so unstable
that it decomposes at 0 0C already. The C H CH - CHPC14-PCI- yield amounted
6 5 3 6
to 80%. When the complex Is reacted with SO 21 styryl phosphinic acid di-
chloride forms in a high yield (Ref.7). Styryl phosphorus tetrachloride is
obtained under the action of styrene. When reduced with red phosphorus
(Ref.8)t the complex is converted into styryl phosphine dichloride. All
these chemical conversions together with the analytical data confirm the
Card 2/3
87532
Reaction of Phosphorus Pentachloride With 5/079/60/030/012/016/027
Unsaturated Hydrocarbons BOOi/Bo64
structure of the complex. When heated, the complex decomposes to HC1,
PC1 3' and halogenated hydrocarbons. The unstable styryl phosphorus tetra-
chloride could not be obtained in the pure state; its structure was. how-
ever, confirmed by its conversion into styryl phosphinic acid dichloride
under the action of S02 and by reduction with red phosphorus to styryl
dichloro phosphine. Similar complexes of the ArPCI 3' PCI6type were
synthesized by reacting PCI5 with aryl phosphinic acid dichloridea;
ArPOC1 4 2PC1 )POC1 + ArPCI+.Pcl - There are 9 referencesi 4 Soviet,
2 5 3 3 6'
6 US, 1 British, and 3 German.
ASSOCIATIONs Institut organicheskoy khimii Akademii nauk Ukrainskoy SSR
(:nstitute of Organic Chemistry of the Academy of Sciences
Ukrainskaya SSR)
SUBMITTEDt January 28, 1960
Card 3/3
5/07Y60/0 3 0/012/017/02 7
GS0 B001 Zo64
AUTHORSt Zhmurova, I. N. and Kirsanov, A:.V1_
TITLF.3 Hydrolysis and Acidolysis of Monomeric and Dimeric Trichloro--
phosphazoaryle
PERIODICALs Zhurnal obahchey khimii, 1960, Vol. 50, No. 12, PP-404B-4053
TEXTs The trichlorophosphazoaryls (IrN - PC1 3) obtained in the previous
paper (Ref.1) are easily hydrolyzed by air moisture. They acidolyse with
formic and acetic acid to aryl amidophosphoric acid dichlorides (I)-(IV)
(Table 1). In contrast to monomeric trichlorophosphazo aryls the dimerio
compounds are not transformed in-to aryl amidophosphoric acid dichlorides
durin hydrolysis or acidolysis. Dichlorides of the arylamidophosphoric
acid IV)-(XII) (Table 1) may be obtained by the method described in Ref.1
under the action of formic acid on the solutions of monomeric trichloro-
phosphazoaryls according to reaction (A). The latter are easily hydrolyzed
with water (some of them even by air moisture) which renders their
purification difficult. On prolonged heating in dissolved state or on
water bath without solvent, they gradually decompose. The authors proved
Card 1/3
Hydrolysis and Acidolysis of Monomeric and S/07Y60/030/012/017/027
Dimerio Trichlorophosphazoaryle BOO1 B064
the identity of arylamidophoaphoric acids which are mentioned by
Michaelis (Ref.2). On reacting PC15 with arylamidophosphoric acid di-
chlorides the initial products were obtained in high yields, i.e., the
monomeric and dimeric trichlorophosphazoaryls (Ref.1)s
ArNHPOC12 + Pol5-> FOC1 3 + HCl + ArN- PC1 3
2 ArRHPOC12 + 2PC15 2POC13 + 2HC1 + (ArN - PC1 3)2
The structure of dimerie trichlorophosphazoaryls could be determined by
partial hydrolysis only in four dimers. According to the elementary
analysis, their molecular weight and the chemical properties, the
reaction products obtained in this connection are acid chlorides of
N,Nl-diaryl-N-dichlorophosphinyl diamidophosphoric acid (Table 2). All
other dimers gave only viscous resins. In crystalline state
N,Nl-diaryl-N-dichlorophosphinyI diamidophosphoria acid chlorides are
rather stable; on heating in organic solvents or POCI 30 they rapidly
decompose. Their structure was confirmed by converting them into the
dimeric initial trichlorophosphazo aryls with 2 moles PCI 5* There are
Card 2/3
Hydrolysis and Acidolysis of Monomeric and S/079/60/030/012/017/027
Dimeric Trichlorophosphazo&ryle B001/Bo64
2 tables and 2 referencest 1 Soviet and 1 German.
ASSOCIATIONs Institut organicheskoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences
Ukrainskaya SSR)
SUBMITTEDi January 28, 1960 /~
Card 3/3
",~ ~OVA~J. 2MUVlXVA, L.P.
Derivativen 10f 4-006PUW28micubaside, Zlhw, obg kUms 31 U941,
210-216 Ja 61, (KIFA 3.4121
II* infititut orgskohaskoy kbivnij #k&dwAii mauk Ukraimkoy SSto
(Smiwwbaside) -
89519
3/079/61/031/002/012/015
BI 1 8/B208
jUreanov, A. V. and Shokol, V. A.
Aryl eaters of N-diaroxy-phosphinylimino-thiocarboxylic acids
of the aromatic series
Zhurnal obahchey
TEXT: Thediesters of thioaoyl-phosphamic acids ArC(-S)NHPO(OR)2 synthesized
by the authors in Ref. I re tautomeric with li-diaroxy-phoophinylimino-thio-
carboxylic acids (I) Arc r. NPO(OR)21SH. The aromatic eaters of the latter
were obtained by reacting the chlorides of N-cliaroxy-phosphinylimino-
carboxylic acids (Ref. 2) with sodium thiophenolates, or (with particular
ease) with thiophenols in the presence of tertiary amines:
+ MAP + (C H
Arc NPO(OArt) C1 - a, 5) 31) Arc NPO(OArI )2 SAr". The eaters
I or NaSAr" I
are insoluble in wator# alkali lyes, and acidn. p-Nitrophenyl eaters of H-
diaroxy-phoophinylimino-thiocarboxylic acids are gradually decomposed on
Card 1/3 #
89519
1079J61/031/002/012/019
Aryl esters of N-diaroxy- i-118/B208
heating (250-30000 in high vaouum to give nitriles, and also considerably
carbonized. As far as the chemical propertise are concerned, the esters (I)
mu ch resembl:,!he ail esters of N-diaroxy-phc3phinylimino-carboxylic acids
(Ref- 3). E re (, are easily saponified with aqueous-alcoholic solutions
of strong mineral acids, and with 90% acetic sooid. When treating the esters
(1) with NH 3 or amines, the corresponding ami(ines and thiophenols are
obtained:
ArC [_ NPO(OArl) 2] SAr" + RNH2 ? Ar"SH + , rC [_ NPO(OAr') 2] NHR.
In alcoholic solutions, the esters (I) react iith NH very easily and with
nearly quantitative yields. The reaction of he eaths (I) with amines is
much more difficult, and requires prolonged h#ating (up to 35 hr). To com-
pare the properties of the esters (I) with th- aryl esters of N-diaroxy-
phosphinylimino-carboxylic acids (Ref- 3), thi- reaction of the latter with
NK3 and amines was studied. The aroxy*group if these aromatic esters, which
is combined with the carbon atom, wai found t( be also substituted by the
amino group, on the action of NH or amines, giving the corresponding
amidines and phenols: 3
Card 2/3
89519
S/079/61/031/002/012/019
Aryl esters of N-diaroxy- B118/B208
ArC I -NPO(OArQ 2] OAr" + RNH2 0 Ar"OH + ArC [_ NPO(OAr' )21 NHR.
Concentrated HNO hydrolyzes the esters (I) to diesters. When heating the
esters (I) with 3dimethyl sulfate at 1000C, without solvent, no alkylation
occurs at the sulfur atoml the initial prodict gradually changes to form
nitriles, thiophenols, diesters of acyl-phc3phamic acids, and other
products of unknown structure. The sulfur in the esters (I) thus has not
the properties of sulfide sulfur. There aisi 4 tables and 7 references:
5 Soviet-bloc and I non-Soviet-bloc.
ASSOCIATION: Institut organicheskoy khimi~ kkademii nauk Ukrainskoy SSR
(Institute of Organic Chemis-ry of the Academy of Sciences
Ukrainakaya SSR)
SUBMITTED: March 7, 1960
Card 3/3
AUTHORS:
TITLE:
PERIODICAL:
89520
8/07gj6l/031/002/013/019
B118/B208
Fedorova, 0. K. and Kiroanov, A. V.
Reaction of dichlorides of alkyl phcephinic acids with
phosphorus pentachloride
Zhurnal obahchey khimii p v -. 31 1 no. 2, 1961 t 594-598
TEXT: On reaction of the diohlorides of aryl phosphinic acids with PC159
crystalline complexes ArPC1, 'PO16 are formed, as has been shown by the
authors in Ref. 1. The purpose of the present study was to clarify whether
this reaction is specific only for the dichlorides of aromatic phosphinic
acids, or holds for the dichloridee of aryl a n d alkyl phosphinic acids.
The authors studied the reaction of P015 with dichloridea of ethyl-, propyll
and butyl phosphinio acids, and found that under mild conditions (i- ben-
zene, at 8000)_not only the dichloro phosphinyl group is converted to the
group PC1*-PCl
3 6, but also complete chlorination of the a-carbon atom occurs
giving complex compounds of PC1 5 with a, a-dichloro-alkyl phosphorus tetra-
Card 1/4
a9520
8/079/61/031/002/013/019
Reaction of dichlorides B118/B208
chlorides:
RCH2POC12 + 4PC15 2HC1 + 2PC1 3 + Pool3 + RCC1 2PCl3.PC1 6' The positIm
of the chlorine atoms in the alkyl groups is confirmed by the fact that the
complex C2H3 C12pol3 0FC16 gives with 802 the dichloride of dichloro-athyl
phosphinic acid which corresponds to that obtained by A. M. Kinnear (Ref. 2)
from a, a-acid. The complexes RCC1 PCl+ - (Tablel) are insoluble in common
2 3-06
solvents, and react vigorously with water and alcohols, they are hydrolyzed
at different rates depending on the character of the radical. The complex
CH CM PCI +-Pei- is hydrolyzed with water at 200C, splitting off about nine
3 2 3 6
chlorine atoms, and about ton chlorine atoms when boiling with water for
two hours; the last chlorine atom cannot be split off even by prolonged
boiling. The complexes C H eel Pei+.Pcl- and n- C3H7 eel Pcl+.Pcl- are
2 5 2 3 6 2 3 6
hydrolyzed by boiling with water for one hour, splitting off all chlorine
atoms. Reaction of sulfur dioxide with the complexes
RCC1 Pcl+.Pcl-(R-CH H # n- C3H7) gives the dichlorides of a, a-dichloro-
2 3 6 39 C2 5
Card 2/4
89520
9/079/6.1/031/ow/oi.~/Olq
Reaction of dichlorides ... B118/B208
alkyl phpphinio acids:
RCC1 PC1 Poll- + 2SOf---), POC1 + 2S001 + RCC1 POC1 The compl4x
2 3* 6 3 2 2 2'
CH3 Ccl2POC12 (1) first synthesized by A. M. Kinnear (Refo 2) has not been
characterized in detail. It is crystalline, distillable in vacuo, causes
weeping, and is well soluble in organic solvents. When treating complex (1)
with alcohols in the presence of pyridine monoalkyl esters of the monoacid
chloride of a, a-diohloro-ethyl phosphinic acid (II), CH 3CC12PO(OR)Cl are
formed. They have a fruitlike odor and possess insecticidal properties.
Complete hydrolysis of the dichloride of a, a-dichlorobutyl phos, inic acid,
or of the complex n-C H CC1?Cl+o gave a-ketobutyl phosphinic acid
.3 7 6
(n-C3 H7COP(OH)2) which is stable in aqueou -a acid solutions (Ref- 4).
M. 1. Kabachnik and P. A. Rossiyekaya are mentioned. There are 2 tables
and 5 references: 3 Soviet-bloc and 3 non-Soviet-bloc.
ASSOCIATION: Institut organicheskoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences
Ukrainskaya SSR)
Card 3/4
89520
8/07 9 /61/031 /002/0131019
Reaction of dichlorides - e.-. Bil8/B208
SUBMITTED: March 14, 1960
Card 4/4
89521
S/07-651/031/002/014/019
B1187B208
AUTHORS: Kirsanov, A. V and Zhuravleva, L. P.
TITLE: N-dichloro-phosphinyl carbamic acid
PERIODICAL: Zhurnal obshchey khimii, v. 31 9 no. 21 1961 , 598-604
TEXT: It was to be expected from Ref. 1 that N-dichloro-phosphinyl carbamic
acid formed by treating the dichloride of isocyanato-phosphoric acid with
water splits off readily C02 being converted to phosphamic acid dichloride.
Experiments disclosed that isocyanato-phosphoric acid dichloride readily
sPlits Off C02 with excess water, in which connection, however, the acid
chloride part of the molecule is hydrolyzed:
Cl 2PONCO + 4H 20 )ICO2 + 2HCl + NH4H2PO 4' Addition of water only to the
isocyanate group, without hydrolysis of the chlorine atoms bound to phos*=4
was possible only by the method of R. Graf (Ref. 2), i.e., with concentrated
hydrochloric acid. In this way the dichloride of isocyanato -phosphorio
acid gives the thermostable N-dichloro-phoephinyl carbamic acid M:
Card 1/3
89521
8/079/61/031/002/014/019
N-dichloro-phosphinyl ... B118IB208
C12PONCO +H20 i0 C12PONHCOOH. Its structure was Ponfirmed by analytical (kta
and the following reactions: 1) Complete hydrolysis gives HClj NE 39 COV
and H 3PO41 2) reaction with PC15gives HC1, POC13 , and C12PONCOi 3) trialkyl
phosphates are formed nearly quantitatively with alcoholal 4) with aniline,
the aniline salt of N-dianilidophosphonyl carbamic acid rZ ultsi 5) heating
to 1600C gives HC1, 012PONCO, and the polymer CHOPO - NCO H1 - The aniline
salt of N-dianilidophosphinyl carbamic acid obtained from N-dichloro phos-
phinyl carbamic aoid and aniline hydrolyzes when treated with alkali lye to
give the sodium salt of dianilidophosphoric acid, aniline, soda, and NH
Mhen heating N-dichloro-phosphinyl carbamic acid, the following processi;
take place successively:
0 0
100 10001
2C12POSHCOOH C12PONCO + I [HOP0 (- NCOOH)j x 100 P -i'(HOPONH)x
I (PON)
x x
Card 2/3
89521
S/079/61/031/002/014/019
N-dichloro-phosphinyl B118/B208
The thermal stability of N-diohloro-phosphinyl carbamic acid and N-carbmy-
metaphosphimic acid is probably due to an aromatic structure formed by a
hydrogen bond. There are 9 references: 1 Soviet-bloc and 8 non-Bftet-
bloc.
ASSOCIATION: Institut organicheskoy khimii Akademii nauk Ukrainskoy SSR
(Institute of Organic Chemistry of the Academy of Sciences
Ukrainskaya, SSR)
SUBMITTED: March 21, 1960
Card 3/3
3/079 6!1031100310!310!3
B?fPYB207
AUTHORSt Levchenko, Ye. S. and lirsanov. A. V.
TITLEi Nomenclature of compounds containing tht- N-S double bond
PERIODICALt Zhurnal obshchey khimii, v. 31, no. .5, !961, 10A0-1042
TEXT: Comparatively few of such compounda have hitherto been knivn so that
their nomenclature was or no practical Importance. Since, h-1wever, recently
the number of new types with the above bond has considerably increased, a
suitable nomenclature has become indispensable. The aulhors take account of
the nomenclature suggested by R. Appel et al. (Ref. 2s Lieb. Ann., 6!8, 53
(1958)), 1. Whitehead, H. Bentleyl they are of the opinion that the nomen-
clature to be developed should not deviate from the ritles of nomenclature
holding for other classes of compounds, and that it should chara-:.terize th
chemical nature of the compound an clearly as pcssible, including the degre:
of oxidation of the atom determining the class of the compound in question.
For this reason, the authors regard I. Whithead's and H. Bentlkey'6 sugges-
tion as insufficient since the following principle holds for their nomen-
claturet If an imino group adds to the male~,ule of the comp:iund, its name
Card 1/5
S/0.79~61/031/00i/013/013
Nomenclature of BIJO/B207
receives the enling "imine". This principle is little used in other olasses
of compounds qnd cannot be applied to the majority of izlsoses of .compounds
whose RN. or IM. groups are linked with other atoms by double bonds. Ac-
cording to Whitehead's and Bentley's suggestion, aidimines (aldehyde imines)
RC(v-NH)OH would have the name "alkyl idenimines" since thti NH- group adds
to the alkyl idenes. The rules of nomenclature that have been :n use for a
long time, for compounds with both NwC and C-S bonds, should not be changed.
Besides, the above principle does not characterize the chemical nature of
the compounds. Compounds with R 2S-NH bonds are no derivatives of sulfides,
but of sulfoxidos so that their name should characterize their relationship
with sulfoxides and not with sulfides. Compounds with the R 2S-NH bonds also
belong to the sulfoxides, just as the aldimineo belong to the aliehydes and
the imino acids to the acids, so that these compounds should be termed sulf-
oxide . imines and not sulfide imines. The ending "imine" cannot determine
the valency state, since in aldimines and ketimines the valency of carbon is
the same as in aldehydes and ketones. The authors recommend the following
principles for the nomenclature of compounds containing HN. or RN-groupst
1) The HNo group should be called imido group only if it, is linked with two
Card 2/5
1"oz.-Inclature of ... B110/B2407
1~ 2) The FEN. Group should be oalled imino group only if it is linked-
with both bonds to one atom only- 3) The names of compunds with an No$
bond (or 11-P bondq eto.) should be derived from the names of t-he rospoctivo
oxyUk-ni conpounds and completed by the endina "imine". For the individual
clazs~;.; of compoundo with tin N.S bondp the namee listed in the talule are
uur-aested. There are I table and 6 Soviet-bloc reforencee. 'he 3 rofer-
encoc to EnC;lioh-lanGuage yublications read as follow:;: N. Bcn.'.Iey, 1.
'iftlitelic-d, J. Cham. Soc., 1950, 11081; V. Smith, C. TullueL,,, R. S.-Ath, V.
EnZ;clhardt, j. Ar.. Chem. Soc. , 82, 551 (1960); G. Kosolapoff, OrGanoihospLo-
ru.- comijoundo, N. Y. (1950).
ASZOCIIATIO10 Inutitut organichookoy khinii Ali VSSP (Institute of Organic
Chemictry AS UkrSS111)
SUB:111MM: July 25o 1960
Cara 3/5
FZSHCHENKO N. G. ; AIRSAAQV
0 ~, A.V.
Phenyl - and diphenylphoBphoruo iodides. Zhur. ob. khim. 31
no.4:1399-2400 Ap 161# (HIRA 31,:,4)
1. Institut organichaskoy khimii Akadeviii nauk Ukrainskoy SSR.
(Phosphorus compounds)
KROPAVHffA, A.A.j DERKACH, G.I.) KIRSANOV, A.Y.
N, NO, NN-Trieth;rlenotriamidophosphaso compounds and NO. Nw, V'w-
triethylong-H-diamidophosphinylArem-lAiness Zhw.ob.kUm. 31 -
no.5t1601-1604 MY 161. (KMi 14 0)
le Inotitut organiobaskoy khiaii Akadeaii nauk Ukraiwkoy SSR,
(Phosphaso compounds) (Amidings)
KIRSANOV, Mal HARENSIS, H.S.
Therml ol*aTW of phaWl trichlorophosphasocarbonatee Zhurpobt
kbit, 31 zioe5iI605-1607 IV 161, (KM 1415)
L Institut organiobeekoy IthJuil AN Ukrainskoy SSR.
(Phosphaso compounds) (Carbonic acid)
KIRSANOV, A.V.; I NOWS, H.S.
Eaters of urathanphpophorio aoidis Part 2. Zhur.ob.kbin. 31
no. 5 tl6M-l6nW Y.61. (KVU 34t4)
I@ Ino4tut orgwdcbaskc7, MI-14 AN Ukrainskoy SSR.
(Urethai2phosphoric aoid)
IZVCHENKOO less*) JIIIISANOIIL A.V.
N-arylaulfozzy1iminothionyl, chlorides. Zhw.ob.khim. 31 no.6t1968-
IM ;a 161. (KIRL 14s6)
L Institut organichaskoy kidmil AN ukrainskoy m.
(Thionyl chloride)
(sulfonio aoicla)
WCHENKOI Ye.Soj DERKACH, N,Ya*j KIRSANOV, A.V.
Chlorides of N-ar7loulfonylarenimin sulfouic acids* Part 2. ZhIW.ob.
khim. 31 no*6tl973.-1976 To 161. (KM 14s6)
'I* Institut organichookoy khimii AN Ukrainskoy MR.
(Sulfonic aoide) (Chlorides)
SHOKOL) Y.A.; KIRSANOV,. A.V.
Ni-dilLroxnhosphinyl-N2(N3-qrylthioc.arbenizql) arenazoidines
(NI-aryl-Nz()13-diaroxypb,oophinyliminoaroyl)-thiourea). Zbur.
ob.khim. 31 no-712275-2282 Jl 161. (AVA 14:7)
1. Institut organichesk6y Irbi-ii AN Ukrainskoy SSR.
(Urea) (Amidineo)
LEnHEM, Ye.S.1 KO=V, F,.S,; KIRSANCY4-A,-Y.
N-carbethwVareneimino sulfonyl chlorides. Zln,r.ob.khim- 31 no-7t
2381-2385 In 161. (MM 14:7)
lo Inatitut organicheskoy khimli AN Ukrainskoy SSR.
(Sulfonyl chlorides)
DEWCHI G.I.; DREOVALI, G.F.; KIRSANOV A V.
Triaryloxy phosphazo-N-~.arvlsulfonyliminobenzoyls and N-
diary;oxyphosphinyl-NO-aryli3ulfonylbenzamidines. Zhur.ob.kmm.
31 no.7s2385-2390 JI 161. (MIRA 14:7)
1. Institut organicheskoy kbimli AN Ukrainakoy SSR.
(Phosphorve organic compounds) (Benzamidines)
DEWCH, G.I.; laWZEMENT-PRIKHODIKO, V.V -ji~M~lv ~
H-diaminophosphiiql"oylamides. Zhur.ob.khim. 31 no,7:2391-2396
11 61. (MIRA 14:7)
L.. Institut "ganiohookoy khimii AN Ukrainokoy SSR.
(Phosphinic amide)
SHEVCHENKO# V.I.-, SHTEPANEK, A.S.; KIRSANOV, AN.
Isocyanatephen.vlphosphinyl chloride. Zhur.ob.khim. 31
no.9:3062-3066 3 161. (MM 14:9)
1. Institut organicheakoy kbimii AN Ukrainakoy SSR.
(Phosphinic chloride)
DERKACH, G.I.; ISProus A.M.;
Alkyl esters of N-dialkoxy- and N-diaroxypbosphizqlindnocarboxy]Ac
acids. Zhureobakhim. 31 no,10:3424-3433 0 161. (HIRA 14: 10)
1. Institut orgaaicheakoy WWI AN Ukrainskoy SSR.
(Eaters) 'f' A-Am, Orgwdo)
PROMENK09 L.D.1 DERWHI 0.1.1 KMANOV. A.V.
Bintrietbylenetriamidophosphazo derivatives of dibasic acids
and diethylonediamidoo of bie-N-diethylonediamidophosphirqlimirio-
oarboxylic acids. Zbw.obakhim. 31 no.10:3433-3436 0 161,
(KMA 14: 10)
1, Institut organicheakoy kbim4i AN Ukrainskoy SSR i Mcrainskiy
nauchno-isoledovateltakiy sanitarno-khImichaskiy institut.
(Acids., Qrganic) (Phosphazo compounds)
DSRXACH, 0,I.j GUBNITSKAYA, Ye.S.; KIRSAVOV A V.
TriphwqlphoophazoaroY:Loj, N-diphopylphosphInylphanylaryl ketiminest
and N-diarylphosphinylaroyl amidess Zhur. ob. khim. 31 no. H33679-
3684 N 161. (MMA 14:3-1)
1. Institut organichookoy khlmli AV Ukrainakoy SSR.
(Phosphorus organic compounds)
ZHMOVA, I.N.1 KOSANOV, A.V.
Plionyldichlorophosphazoaryls. Zhuro ob. khim. 31 no. 110685-3689
N 161. (MMA 14:11)
1. Institut organichemkoy khimii AN Ukrainskoy SSR.
(Phosphoruo organic compounds)
ZHKUROVAp I.N.1 VOYTSEKHOVSKAYA., I.Tu.; KIRSAPOV, A.V.
Triphenoxyphosphazoaryle, Zhur. ob. khim. 31 no. 110741-3764
N 161. (MIRA 1401)
lo Inatitut organicheskoy khimii AN Ukrainakoy SSR.
(Phosphazo compounds)
DFIMCHO G.I.j GUBNITSKAYAp Te*S*j KILSANOVO A.V.
TrJAMIJAOphosphazoaroylB and N-dianilidophosphlnyl-NI-aryl-
arenimidines, Zhur. ob. khim. 31 no. 11:3746-3750 N 161.
(HIRA 14:11)
1. Institut organicheskoy kh4mii AN Ukrainskoy SSR.
(Pbosphazo cmpounde) (Amidinoo)
31190
S/079/61/031/012/004/011
b228ID301
AUTHORS: Ivanova, Zh. M., and Kireanov, A. V.
TITLE: The aryl trifluoromonohydrides of phosphorous
PERIODICAL: Zhurnal obshchey khimii, v. 31, no. 12, 1961, 3991-
3994
TEXT: The preparation of the aryl trifluoromonohydrides of P is
described together with data for some of their properties. In the
present study, however, the authors used KHF since they were un-
able to verify the data previously obtained &ith SbF 3* Three aryl
difluorophoaphines were prepared by heating solutions of KHF2, and
aryl dichlorophosphines till Via reaction commenced (50-600)t pu-
rification being effected by vacuum distillation in an atmosphere
of N2* Their yields and boiling points were: a-MeC 6 H4PF3H - 79%9
90-910; PhPF 3H - 84%, 57-580(1); and n-ClC6H4PF3H - q* 90-910(11).
The structure of these compounds was also confirmed by chemical
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