SCIENTIFIC ABSTRACT VANAG, G.YA. - VANAG, G.YA.

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• Collection: Scientific Abstracts
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• Original Classification: S
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• Document Creation Date: November 2, 2016
• Document Release Date: August 31, 2001
• Sequence Number: 8
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

66461
.44~ 57,3900 SOV/20-129-1-2'1/'64
AUTHORS: Aren, A. K., Vanag, G. Ya., Academician,AS LatvSSR
TITLEi 2 -Ethyl eniftas-2 --ph -en-yTi-A-ta ndi one - 1 3
PERIODICAL: Doklady Akademii nauk SSSR, 1959, Vol 129, Nr 1,
pp 98 - 101 (USSR)
ABSTRACT: The authors have been studying the amino derivatives of 2-sub-
stituted indandiones-1,3 for several years (Refs 1-5). These
compounds are not only of theoretical but also of practical
interest because_many of them are physiologically effective
(Ref 6). The authors also attempted to introduce the ethylene-
imine group into the indandione molecule. P_ diketones containing
the latter group in their active methylend group have not been
described., The compuund named in the title (II) is formed
even at room temperature by the interaction of 2-bromine-2-
phonylindandione-1.3 (I) (see Diagram) with ethylenfl~in
ethereal oolution. For economLcal. rpasowj triethylamine (Ref 7)
may be used inatead of ethylenimine for the. combination of
hydrogen bromide. The substance cited in the title is greenish
yellow, crystalline, and readily soluble in organic solvents.
If its solution in absolute ether is saturatcd
with hydrogen chloride, a white, salt-like HC1 salt of 2-
Card 1/2 chloroethylamino-2-phenylindandione-1,3 (III) is precipitated.
L~__

66481
2-Ethylenim-iTici.-.g.-2-phenylindandione-1 3 SOV/20-129-1-27/0'4
It was formed due to the opening of the ethylenimine rin6 by
HC1. Hydrogen bromide and hydrogen iodide have an analogous
effect (Refs 8,9). The authors proved (in contradiction to
.1. Yu. Lidak, S. A. Giller and A. Ya. Medne (Ref 7) that hy&rogen
halides open the above mentioned ring in an anhydrous medium.
The structure of (III) mentioned (see Diagrar.) was proved to
be correct by the synthesis of substance (IV described earlier
(Ref 2) which could be transformed into (Ilfl by the effect of
thionyl chloride. Since the compound contains a secondary amino
group it yields a corresponding nitrosq- and acetyl derivative-
The authors thank M. Lidak for the ethylanimine provided by
him. There are 11 references, 7 of which are Soviet.
ASSOCIATION: Rizhskiy politekhnicheskiy institut (Riga Polytechnic Institute)
SUBMITTED: July 10, 1959
Card 2/2

5W At
AUTHORS: Neyland, 0. Ya. p Vana~-'/.J;- (Riga) SOV/74-28--4-4/6
TITLE: ectroscopic Investigation Methods of the Tautomeriam of
Y-Dicarbonyl Compounds (Spektroskopicheskiye
metody issledovaniya tautomerii ~-dikarbonillnykh
soyedineniy)
PERIODICAL: Uspekhi khimii, 1959, Vol 28, Nr 4P PP 436-464 (USSR)
ABSTRACTs In this survey the authors attempted to generalize the
existing material on upectroscopic investigations of
keto-enols. At the same time several theoretical questions
occurring in connection with spectroscopic data are
discussed. In order to systematize the existing material
above all various states and forms of equilibrium of
P-dicarbonyl compounds had to be investigated. The diversity
of the possible forms indicates complicated phenomena of the
tautomerism of keto-enols thus Justifying the application
of spectroscopic investigation methods. Moreover, spectral
properties of the individual forms are characterized. The
dicarbonyl form (I) of the aliphatic and alicyclic
P-dicarbonyl compounds has no chromomorphous system but
Card 1/6 only 2 isolated carbonyl groups. For this reason it is

Spectroscopic Investigation Uethods of the Taut=eriam of SOV/74-28-4-4/6
-Dicarbonyl Compounds
characterized in the usual ultra violet zone by an only
small absorption at 270 - 290 m~. The absorption 7one of
the carbonyl groups is rather broad for various types of
carbonyl compounds. But in the case of an individual type
and even an individual compound the position of the maximum
changes according to the polarity of the solvent. In the
transition of a polar (e. g. methanol) to an apolar (e. g.
hexane) solvent a bathochromic shift is observed (a shift
of the absorption maximum in the direction of long waves)
(Ref 10). Unsaturated or aromatic P-dicarbonyl compounds
show a very complicated picture. In these cases there is
a characteristic chromomorphous system, carbonyl group -
double bond (aromatic cycle), which absorbs intensively in
the respective zone. In computations the absorption of the
dicarbonyl form F, k ~0 has to be considered which renders
the determination of the quantity of the enol form very
difficult. Valence oscillations of the non-conjugated
carbonyl group are characterized by the fz nuencies
Card 216 1700 - 1750 cm-1 (Refs 14, 15) and can be clearly distinguished

Spectroscopic Investigation Methods of the Tautonerism SOY/74-20-4-4/6
of ~_Dicarbonyl Compounds
in infrared as well as in Haman spectra. In the case of a4hatic
P-dicarbonyl compounds with an eater arrangement
(acetoacetic eater, eto) 2 characteristic frequencies cf
the dicarbonyl form are observedt that of the ketono
group and that of carbonyl ester in the range of
1710 - 1715 cm-1 and 1739 - 1745 cm-1, respectively. This
bipartition of the characteristic frequencies goes back
to the mechanic interaction of the oscillations of two
independent carbonyl groups (Ref 19). Among the structural
factors especially the substitution by halogen atoms at the
X-carbon atom influences the degree of the characteristic
frequencies. The simplest prototype of the tnol form are
the O(L, a -unsaturated ketones or 0C, (b-unsaturated
carboxylic acids (111). Such a chromomorphous system is
characterized by an intensive absorption in the wide
ultra-violet range according to the nature of the substituents
R1' R2' R3' and 'N which influence the position of the
absorption maximum. The enol form is mainly characterized
Card 3/6 by the valence oscillations of the carbonyl group, the

Spectroscopic Investigation Methods of the Tautomerism SOV/74-28-4-4/6
of ~-Dicarbonyl Compounds
double bond and the hydroxyl group. In contrast to the)
dicarbonyl form of aliphatic and alioyclic compounds ive have
in this cave a conjugated carbonyl group no well as a
conjugated double bond. In the case of a free enol form the
recognition of the individual bands becomes more difficult
because an intramolecular hydrogen bond may be formed at the
expense of the hydroxjl or carbonyl group. The hydrGeen bond
may change the frequency of the carbonyl group which then
may coincide with the frequency of the double bond. The two
characteristic frequencies appear most distinctly in Raman
spectra. Some authors found a relation between the nature
of the metal in the complex and the frequency r:iift. The
fluctuations of the hydroxyl group of the -dicarbonyl
compounds appear in the wide range of 2500 3500 cm-1
because of the presence of various hydrogen bonds according
to structure, solvent, concentration, and admixtures (Ref 14).
The classical method by Meyer (Ref 43) which was supplemented
by Dieckmann (Hef 44) and accelerated by Schwarzenbach
Card 4/6 (Ref 18) is still valid for the determination of the enol

Spectroscopic Investigation Kethods of the Tautomerism BOV/74-28-4-4/6
of P-Dicarbonyl Compounds
content. The enol content can also be determined by using
several spectral properties of the keto-enols. The
investiGation by infrared-spectroscopy seems to be very
promising. Usually, the dissociation constants of
keto-enols are determined in the same way as those of
other acids, i. a. electrometrically. In the case of
keto-enols there are still other possibilities, i. e. the
application of ultra-violet absorption spectra. Numerous
investigations showed that Meyer's law is not valid for a
large group of Vdiketones. In these cases the method of
infrared and, in part, ultra-violet-spectroscopy can be
successfully used. However, the tautomeriam of
trans-fixed ~-dicarbonyl compounds is still very !unclear
and requires further investigation. The behavior of some
alkylidene acetylacetones which was discovered by means
of spectroscopy is also interesting. Table 1 - characteristic
frequencies of non-=IjUgated dicarbonyl form; Table 2 -
characteristic frequencies of conjugated dicarbonyl formi
Table 3 - ultra-violet absorption of undiseociated enol
Card 5/6 form which may exist in ciB-form; Table 4 - ultra-violet

Spectroscopic Investigation Methods of the Tautomerism SOV/74-28-4-4/6
of P-Dicarbonyl Compounds
absorption of trans-fixed P-dicarbonyl compounds and
their derivatives; Table 5 - ultra-violet absorption of
the enolate anion and enolate cation; Table 6 - characteristic
frequencies of the enol form in the range of double boadsi
Table 7 - characteristic frequencies of the hydroxyl group
of P-dicarbonyl compounds; Table 8 - characteristic
frequencies of intramolecular metallic derivatives of'
P -dicarbonyl compounds. There are 6 tables and 88 references,
24 of which are Soviet.
Card 616

GUDRINIEGEO E.J VANAGs G. [Vanags,G.1; TIM, E.
Research in the field of cyclic arylazo-,J.-diketones. VIII. Condensa-
tion of 5-phenylcyclohexanedione-1,3 (phenidone) and 4-carbethoxy-
5-phenyleyelohexanedione-1,3(4-carbothoxyphenidone) with diazotized.
aromatic amines. Vestis Latv ak no.2:87-94 160. (EM 10:1)
(Phenyleyclohexanedione)
(Phenidone) (Ethoxycarbonyl group)
(Aromatic compounds) (Cyalic compounds)
(Aryl groups) (Amines) (Ketones)

VANAGjG.Ejanags,G.](RigeL); STUNDA,L(FUga)
2-nitro-4v 5-dimethoxyindandions-1,3. In Russian. Testis Laty
ak no.3t77-84 160. (EW 10:7)
1. Akademiya nauk Latviyokoy SSR, Institut organichsekogo sinteza.
(Nitro group) (Dimethoxyindandione)

GEYTA,L.[GeitalL. ](Riga); VANAG,GjVanag9,q. ](Riga)
Condensation of indandione-lt3 -dith furfurole and 5-nitroftrfurole.
In Russian. Vestis Latv ak no.3:93-102 160, (EW 10:7)
1. Akademiya nauk Latviyokoy SSRv Inatitut organicheskofo sinteza.
(Indandione) (Puraldekqde) (Nitrofuraldehyde)

GUDRINI3TSE,X.[Gudr1viec& E ](Riga); IYZV1N1SH,A.[IevinspA.J(Riga);
VANAG, G. Lvanagal, G. I (;Sgt); BRUNEU, V. (Riga); BANKOVSKn,,ru.
'-tBEiFo-vsk1sjJ.1(Riga)
Sulfonation off-diketones. IX. Indandione-lp3-dieulfo-292-aaid
,and its salts. In Russian. Vestis Lmtv ak no.3t103-106 060.
(EW 10:7)
1. Akademiya nauk Latviyokoy SSR, Institut khimii.
(Ketones) (Sulfonation) (IndandimLlfonic acid)

AREN, A. [Arens, A.] (Riga); OZOL,Ya.(Ozol9,J. )(Riga); Vansg,GjVanags,G.1(Riga)
Interaction of 2-halogen-2-p-nitrophenylindandione-1,3 with
aromatic amines. In Russian. Vestis Latv ak no-4-*117-122 160.
(EZAI 100)
1. Akademiya nauk Latriyskoy SSR, Institut khimii.
(Halogens) (Nitrophen3rlindandione) (Amines)
(Aromatic compounds)

VANAG,G..Lvana9sjG. ](Riga); ZHAGATv R. (Zapata, R.) (Riga)
Nitrobrombindon and some of ita color reactions. In Russian.
Veatia Latv ak no.5:77-tO 160. (EW 10:7)
1. Akademiya nauk Latviyakoy SSRI Institut khimii.
I (Nitrobindone) (Bromo group)

NIKOLAMAqN.(Higa)~ VANAGqG.[VanagsvG.1(Riga)
Now effective rodenticidep dlphenylacetylindandione(diphonatsin).
~ In Russian. Vestio Latv ak no.5:81-84 160. (EW 10:7)
1. Akademiya nauk Lmtviyokoy SSR In titut organichakogo sinteza.
(Diphenylacetylindandione~ 'Rodenticides)

AREN't A (Arens, A.](Riga); OZOL, Ya.. [Ozols, JJ(Riga); VANAG, G. tVanags, G.1
jiliga)
Reaction of 2-halogen-2-p-nitrophenylindandione-1,3 with aliphatic
and heteracyclic amines. Vestia Latv ak no.6:61-66 f6O.
(MAI 10: 9)
1. Akademiya nauk Latviyskoy SSR, Institut organicheskogo sinteza.
(Halo e'o) (Aliphatic compounds)
(Heteg n
rocyclio compounds (Nitrophenylindandione)
(Amines)

VANAG, G.[Vanags, G.I(Riga); ZHAGAT, R.[Zagats, R.I(Riga)
Reaction of bindone and some of its derivatives with sodium hydro-
sulfate. Vestis Latv ak no.6:6'1-72 l6o.
(EUI 10:9)
1. Akademiya nauk Lettviyakoy SSR, Institut organic:ieskogo sinteza.
(Sodium dithionite) (Bindone)

1~ VANAG, G,[Vanags, GP](Rjga)j DUMPIS; T.(Riga); ZUTERE, L.(Riga)
2-aminobenzylindandione,1,3. Vestis Iaty ak no.6:73-80 160.
(KW 20:9)
1. Akademiya nauk Latviyakoy SSR, Institut organicheskogo sintata.
(Banzylindandione) (Amino group)

--VANAGpG.[VanagsjOj
Sam reoul.tB of studying A-&ketoneo in the Acadew of Sciences
of the Latvian SSR. In Russian. Vestis Latv ak no,71183-192
160o (EM IN 7)
(Ketones) (Academy of Sciences of the Latvian SSR)

GUDRINMTSE, R.CGudrinlece E.J(P.Iga); IYEMISH, A.I[levins, A.)(&ga);
9 El (Stiptiiece, H.I(Ri'
LG,.(LjVanags, G.I(R%); STIFNIr TS Kh ga
MAT M , X. Emateuss, 3.1 Riga)
Sulfonation of /4-~Lftetones. XIII.Salts of 5-phenyloycloboxanedione-
1. 3-oulfo-2-acid (phanidonoulfo-2-acid. Vestis Latv ak no-8:95-98
W. (EFAI 10:9)
1,, kkadamiia muk L&tviyakay SSR, Inatitut khimi7i.
(Ketones) (Sulfonation) (Phanyleyclohexanedione)
(Phenidone) (Sulfonic acids)

---
A f-Vanags, G.] (Riga); ZKLM, VO(Zelmene, V.)(Riga)
Some 4-nitro-2-phenyl-indand.Lone-1,3 derivatives. Vestis letv ak
no.9:103-108 160. (nAI 10:9)
1. Almdemiya nauk Latviyokoy SSR,, Institut organicheskogo, sinteza.
(Nitro phenylindandione)

AUTHORS-i
TITLEs
PERIODICALs
Gudriniyetse, E.
Kurzemniyeks, A., Grants, Z.
S/153/60/003/01/031/058
BOII/BO05
7nteraction Between Sulfuryl Chloride and Beta Diketones
Izvestiya vysshikh uchebnykh zavedeniy. Xhimlya, i khimicheskaya
tekhnologiyat 1960p Vol 3# Nr 1# pp 119-121 (USSR)
TEXTs The authors proved that sulfuryl chloride is a good chlorination reagent
for cyclic A-diketoneslEtherg dioxanet CC1 41 1,2-dichloroothane, chloroform, and
benzene were used as solvents. The highest yields in dichloroq3-diketones were ob-
tained in dioxane at a ratio OfA-diketone i sulfuryl chloride - I 1 2-5. The re-
action was carried out at different temperatures between 0 and 800. At higher
temperatures, the reaction proceeds faster, but only 2,2-dichlorodiketones-1,3 M
are formed, Without a solvent, the reaction proceeds very vigorously, and the
product becomes resinous. Application of ultraviolet light (quartz lamp) and
anhydrous aluminum chloride did not lead to the formation of sulfochlorides. The
compounds produced are: 2,2-dichloroindandione-1,3, 2,2-dichlorodimedonf),? 2,2-
dichloro-5-phenylcyolohexanedione-1,3t &nd 2,2-dichloroperinaphtSind one. The
table (p 120) shows the reaction temperatures, solvents, yields, and tho calcu-
lated and measured melting points of the products obtained. There are 1 table
Card 1/2

iI
Interaction Between Sulfuryl Chloride and Beta S/153/60/003/01/031/058
Dikstones B010005
and 13 references, 3 of which are Soviet.
ASSOCIATIONt Rizhakiy politekhnicheskiy inetitut; Kafedra organicheakoy khimii
(Riga Polytechnic Institute; Chair of Organic Chemistry)
SUBMITTEW February 23t 1959
Card 2/2

5.56oo r(w3l
SOVI"N - `0-21 -;r2/78
AUTHORS: Neylarld, 0. YA. , Viri,,jl,,, (I. Ya.
TITLE: ol, /3-Dlketoneo. III. Acylation
,ind Alkyl:-itlo-i o1' illi(-,titil(ILrric(lorjyiLo(jone
PIERIODICAL: L L 0 N -
Val .1 r 2,
Ps.,
ABSTRACT: (ZhOlKh, 2'(, 195Y) that
(dimedone) reacts
with
todoberizetle l'orming compouna 1. The same com-
pound io fo,,-nied by the reaction of dimedone nith II,
al.
C a "d 1/6 In the ubove veactlon, acetic ov benzoic acid is

lodor'Lurn FIE"vlvatlve.-~ of, 0 - D I
T f, I.. I on ,twt A I kt, 1, SC
1 .1 J loll of,
P8
PI le I I y I dflic, don y I I ot lon (2
p I I rit 1. 11 n I-, c d:,,n(l v,orfipountl I Is obtalned In a pure otate.
The vel-P:t'loll
L,.4 t:.-Jven below:
Car,d 2/6

YO)
Thc hlt.-! Fro"117IJ:; aod Tiv-lr "ropertle3
0
Nr Starting matevials Obtained Yield mp In c
P),cidliv t,; in
.1. dbledonc. + pholly-1 IC)- 88 156
do!"m "wetate. v CM, 1. 5
-limcdone + plictiy.1 Lo-
dozo benzoate 82 125* (dec)
50 16.1-
,5 T 4- 1001;yl chloride chicircidimetionc,
I + ben-loyl chlorifle VI, 111=C tt (,'0, X=C-L 90 121-122 Her;
5 1 + C 111C 1 + triethyl-
65. 159 (dec)
oxonium boocifItIol'ide
Thc mel.tIng point depre-soLon can be explained by F,-
C " 1, (1 Y6 small adrnlxture of' berivoic acid.

(Table cont 'd)
Y788 1 SOV/1"'(9 - -5(1-p -5',.Jy~3
The Obt-ainef] Prod-l-t:3 ;~,n,.J Their F,ODertle~3
;1- Starting matevIals 0 1) t,,-] I n ed Yle I d in-, In0 C
p poduc ts in %
I + diethyl sulfate +
ammonium borofluorl.de
7 1 + (limethyl sulfate +
+ a=onium borofluo-
ride
Pj I + triethanol
+ dimethyl
9 diphenyldiodonium
bromide + AgOH
+ CH3COOH
phenyl-(O-ethyl-
dlmedonyl.)-iodonilim 7.5
borofluorlde
phenyl-(O-methyl- 41
climedonyl)-iodonium
borofluorlde
VIII, A~Cll3S01,11
diphenyliodonlum
;acetate
1 154
--156 (Dec.
15'3-155 (de!-,)
70.5 110-114 ktecj
44 149-151

'(78B). 3-7jOV,/'(() -30-2 -5' P/(8
Th('-,Ill Propertic',,
The Obtaltied. Product.; all
Nv S11 a v Ll I Obtalned ! Yleld
vocilic. tz;
in %
-1-ItTic(lone
1~0 0-othyl(
+ ('11 COOK -P (11- ("0011
+ complex of' 12 With
cllox,nne
0
mp in c
6.5
Ca-rd ViJ,

I
Iodonium Derivatives of -Diketones.
III. Acylation and Alkylation of
Phenyidimedonyliodone
77881 -2--z2/78
SOV/79-30
X/
(11t 0.
11) (Vill)
ASSOCIATION:
3UBMITTED:
Theve are 2- taibles; Mid 11 vefercnce-~, 4 SovLet, 3
Gemmun, I SwL-,---, '2 U.K. LU.S. The '� U.K. and U.S.
references are: A. T1 - POX,K Pau.",acker-, 3 . Chem.
Soc., "95 (1957); K. II. Pausacker, ibid, '107 (1953);
C.
,, 11. Gold, E. Pfeil, G.
H. Meerwein, E. Tkatteriberf,
WL11fanc,, T. Pv. Chern., 83 (19110).
T
111ga Poly techn ic, al I'n:--)titijte (Rizh.-,Iciy politekhni-
cheolcly in-ItItut)
February 1.91")')
Card 6/6

S/079J60/030/05/29/074
B005/BOi6
AUTHORS: Iyevinlahp A. P., Apinitisp S. K., Gudriniyetse, E. Yu
Vanagy We I&.
TITLE: Sulfonation of P-DiketonesIVII. Crystallographic and X-Ray
Analyses of Alkali Metal and Ammonium Salts of Indandione(1,3)-
-2-sulfonio Acidq
PERIODICAL: Zhurnal obehohey khimiir 1960, Vol. 30, No. 5, PP- 1541-1547
TEXT: The authors of the present paper investigated the crystals of the
lithium-, sodium-, potassium-9 ammonium- and rubidium, salts of
indandione(193)-2-oulfonic acid. To obtain suitable crystals for the
crystallographic investigation, these salts were recrystallized from
aqueous ethanol. The experimental conditions are given. The mono- and
dihydrate of the sodium salt of indandione(193)-2-oulfonic acid were
studied while the remaining 4 alkali salts occurred in anhydrous state.
Crystal class, axial ratio, volume of the unit cell, and number of
molecules in the unit cell were determined for each of these 6 salts.
4 tables give the spherical coordinates of the individual lattice planes
Card 1/2

Sulfonation of P-Diketones. VIL Crystallographic S/079/60/030/05/29/074
and X-Ray Analyses of Alkali Metal and Ammonium B005/BO16
Salts of Indandione(1,3)-2-sulfonic Acid
for the 6 salts investigated. One table shows the parameters of the unit
cells of potassium-, ammonium-, and rubidium salt, 2 further table 11 present
the identity periods for the 3 lattice planes [110], [101], and[0111 for
the dihydrate of the sodium salt, and for the potassium salt of V/
indandione(1~3)-2-sulfonio acid. 4 schemes show the crystals investigated.-
in the oblique and top view. The authors further investigated the
solubilities of the alkali salts of indandione(1,3)-2-sulfonic acid in
water and alcohol at 200. The results are compiled in a table. The
solubility of the salt decreases with increasing radius of the cation.
There are 4 figures, 8 tables, and 2 Soviet referenoes.
ASSOCIATION: Rizhskiyxlitekhnicheskiy institut (Riga Polytechnic
Institut
SUBMITTED: may "? 1959
Card 2/2

S/079/60/030/05/46/074
B005/BO16
AUTHORS: Vanag, G. Ya.,,Stwlkevich, E. I., Gran, E. Ya.
TITLE: Polynuolear HeterooYclio ComMunds,12I. Structure and Color
of Some berivatives of 4,-Phe~iyl-dibenzoylene Pyridine I
PERIODICAL: Zhurnal obshchey khimii, 1960, Vol. 30, No- 5, PP. 1620--1627
TEXT: The authors of the present paper investigated the fine structure
of 4-(p-dimethyl-amino-phonyl)-2 3(CO).6,5(CO)-diben lene pyridine (II)
4-(p zo~
nd -dimethyl-amino-m-nitro-phenyl)-2,3(CO).6,5(co -dibenzoylene
a
pyridine (III), as well as of arylidene indandiones which are the aimplest~
rep resentatives of this series. The absorption spectra of solutions of
these compounds were taken in the ultraviolet and visible spectrum region
and analyzed. Fig. 1 shows the ultraviolet aboorptiont:pectra of two
phenyl-dibenzoylene pyridines in two different solven (dioxane, C 2H5OH +
+ C2H5ONS). Figs. 2 and 3 give the absorption spectra of solutions of
compound (11) in dioxane and in concentrated hydrochloric acid in the ultra-
violet and visible spectrum region. For comparison, in each of these three
Card 1/2

Polynuolear Heterocyclic Compounds. II.Structure 3/079
,/60/030/05/46/074
and Color of Some Derivatives of 4-Phenyl-di- B0051BO16
benzoylene Pyridine
Figs. the absorption spectrum of a solution of 4-phenyl-293(C0~6,5(CO)-
dibenzoylene pyridine W in dioxane is shown. Compound (I) had been
investigated in a previous paper (Ref. 2) * Pi 4 shows the absorption
spectra of com ounds (I) and (II) (In dioxanel*and of 4-(o-hydroxy-
~henyl)-293(CO5.695(CO)-dibenzo,yleng pyridine (X) (in a H OR + C2 H ONa)
in the wave-length range of 200-600 %,A,.. The spectra wi 2nterpretK.
These results suggested the fine strxio'ture of the compounds investigated.
The corresponding structural formulas are given with consideration of the
fine structureo Evidence was offered on the relationship between color
and chemical properties on one hand, and the structure of the compound on
the other. In an experimental part, the syntheses of the compounds
investigated are described. There are 4 figures and 15 references, 6 of
which are Soviet.
ASSOCIATION: Institut organioheskogo sinteza Akademii nauk Latviyskoy SSR
(Institute of Organic Synthesis of the Academy of S iences~
Lai-v-iYekaya SSR)
SUBMITTED: May 25, 1959
Card 2/2

4ANAG, G-Ta.; DUBUR, G.Ta.
Polynaclear heterocyclic compounds. Part 3: Acenaphthenone-l-
spiro-(2:41)-21,3' (GO),615'(CO)-dibenzoylonedibydroprridine.
Zhur.ob.khim- 30 w.6:1898-1904 Je 160.
(KIRA 13:6)
1. Akademiya nauk Iatviyakoy SSR,
(Pyridine)

VAUG MZUL
G ; ,
(;UIRININTS , -k-:J,~,, ketoness Fart 10: suif.,,ation of dimedon-
sulfonation Of ~..Cu l6o.
Zh-ar.ob.khime 30 no.6:1904-1911 Js (glu 13:6)
politekhnicheakiY iuatltut 0
Rizhokiy I dione) (Sujfonl~iou)
(Cyclobexane

lLo
GUDRINrrITSI, J.; VAUG, G.; MAMALIKE, L.
. ..........
Sulfonation of A --diketones. Part 11: Derivatives of 2-dimedon-
sulfoulc acid. Zhur.ob.kbim. 30 no-7:2379-2387 JI '60-
(MIRA 13:7)
1. Rishakiy politekhnicheskiy institut.
(Cyclobammuesulfonic acid- ectra)
(C7clobexane di one -Speo tram

VANAG,G. [VanagsjG.), akadeinikp prof., red.; DIIIARSMA, 0., red.; LEMBERGA,A.,
tekhn. red.
(Cyclic t~ -diketones) TSiklicheskie ~ -diketorty. Riga, Izd--vo Akad.
nauk Latviiskoi SSR, 1961. 372 p. (MIRA .14:11)
1. AN Latviyokoy SM (for Vanag).
(Ketones)

GUDRINIRTSE, Mrudriniece, E.) (Riga); INVINISH, AjIevias, A.I(Riga);
VANAG, GjVanags, G.J(Riga); KWTSBERG, D.[Kreiaberga, D.I(Riga)
Sulfonation of #6 -diketones. IV. Bindonesulfonic acid and its
salts. Yeatis Latv ak no.2:111-111+ 161. (Ew 10: 9)
1. Akademiya nauk Latviyokoy SSR, Institut khimii.
(Sulfonation) (Ketones) (Bindonesulfonic acid)

STRADMI, Ta.[Stradino, J.J(Riga); VANAG, G.[Vanage, G.](Riga); TILTYNt, M.
(Tiltins, 14, J(Riga)
Product of electrolytic reduction of 2-nitroindandione-1,3 dnd 2-
oximinoindandione-1,3. Vestis Latv ak no.22115-122 161.
(Ew 10:9)
1. Akadepiya mauk Latviyakoy SSR, InFtitut organicheakogo sinteza.
(Nitroindandione) (Oximes) (Indandione)

OSMYA., V. [Oskajap V.1t VANAG, G. (Vanags, G.)
Condensation of phthalic anbydride and phenylacetic acid in triethylemim
and acetic anhydride solution. Vestis Laty ak no*3:67-76 161.
lo Institut organicheokogo sinteza, AN Iatviyskoy SSR.

GREN, E.(Grens, B.1; VAEAq,_G Vanags, G.]
4-Mlopentene-Ij,3--dloue and isome of its derivatives. Vestis Latv ak
no.5:65-70 '61.
1. Akademiya nauk LaWyakoy SSRI Inotitut organicheBkogo aintesae

GEYTA, L.(Geitap L.1; ~~T~G anags, G. ]
Reaction of opianic acid with I..3-indandions. Vestis Iatv ak no.5;
79-86 161.
1. Akademiya nauk Latviyokoy SSR,, Inatitut organicheakogo sinteza.

OSHKAYAj V*(Oskaja, V.1; VANAGI_MVamgs, G.]
Condensation of nitrophthalic anhydrides with phanyl acetic acid in
triethylamine and acetic anhydride solution. Vestis Latv ak no.6:
57-64 161.
1. Akademiya nauk latviyokoy SSR, Institut organichaskogo sinte2A.
(Acetic acid) (Phthalic anhydride)

ZHAGAT, R#(Zagats, R.]; VAM, GI[Vanags, G.)
Reaction of bindone with carbonyl group reagenta, Vestis lety ak no,6:
65-70 161.
1. Akademiya, nauk Iatviyokoy SSR, Institut organicheskogo sinteza.
(Bladons) (corbowl group)

ZHAGATp R*[Zagats.. R.jj ZELmENj, VO(243nanep V-1; VANAG, G.[Vanags., G.]
--------
Improved method for obtmining
161. bindow, Vestl# Latv Ak no.6;71,76
3-- AkadsmiYa Mauk Latviyokoy SSRP Institut Orgaaichaskogo sinteza.
(Bindone)

OSHKAYAP V.[Oskaja, V.I; VANAG, G.' a,, G~)
Condensation of phthalic anby1ride with boaxyl oyanide and notb7l-
bezyl ketone in a solution of triethylamlhe and acetic anhydride.
Vestis Latv ak no.8:45-52 061.
L Akademiya nauk Latviyakoy SSRP Institut organicheskogo sinteza,

VANAG G laol STANWICH, E.I.
Polynuclear heterocyclic covipmmds. Part 4: Reaction of bis
(dimedonyl)methanes with a nium acetate. Zlxurob.khim. 30
ncolOz3287-3292 0 161a (MIR& 14:10
la Institut organicheskogo siwbeza Akadendi nauk Latviy-skoy SAj,
(Ammonium acetate) (Yiethane) (Acridinedions)

FREYMANDS, laeFe (Freimanis, J.); VANAG, aYa.
Imines of di- and polyketones. Part 4: Ultraviolet aboorption
spectra structure of iminesof 2-suostituted 1.3~-indandiones. Zh-ur.
ob.khim. 30 no.10:3362-3369 0 ~61. - ' (MM 14:4)
1
I* Institut orgapicheskogo sinteza Akademii nauk Latviyokoy SSR.
(Indandione) (Imines-Spectra)

FREYWIS, Ya*F. (Freimanis$ J.]j--VANAG,-.~.Ya-
Imineo of di- and polyketones. Part 5.- Infrared absorption spectra
and otructure of imineB of 2-substituted indandionea and some of
their derivatives. Zhw.ob.khim. 30 no.100369-3380 0 161,
(KM -14:4)
1. Institut organicheakogo sinteza Akademii nauk Lat7iyakoy SSR.
(Indandione) (Imines-Spectra)

STRAKOV, A-Ta.; MMINIYNTSE, X.Tu.; IMINISE6 A.Y.- TARAG, G-T
_~~q G-Tqr-
I
Sulfonation 0~ Pdiketones. Part 32: Sulfonation of 2-phezql-l,
3-indandione. Zbur. ob. khim. 30 no.12:3967-3972 D 160.
(MIR& 13-.12)
1. Rlxhskiy politekhnicbpskly Institute
Undandione) (Sulfonation)

---, ---- - AMNq -A*K*;--Y rj*Ya.
Synthesije of 2-banzhydryl-113-indandione and its 2-amino derivatives.
Zhur. cLb. khim. 31 no.l.--U7-:L23 Ja 162, (mm 14:1)
1. RizhiIki-y politekhnicheskiy institut.
(Indandione)

Bral , - 0. Ya.; VANAG G Ya.
ljo~j~
Jod6a= derivatives of 10--diketonsaa Part 4S ReactiOn Of 5-PhenYl-
:L~3.cycjohexapedicne with pheyraiodose acetate. Zhur. obe khlm*
31 no.1:146-3.06 Ira 161, (KM 14tl)
1. Rizbeidy po3ltekbnicheolly institut*
(Gy,bl,ohexanedione) (Benzene)

I -
SMKCVt4',A. Ya.; VAIIAG, G. Ya.; GUIRIENTSE.. & Yu.
Sulfonation of p ~diketones. Part 141 Derivatives of 2-(?-oul-
fophenyl)- 1, 3,-indandiclib*- Zhur. ob. khim, 33. no.3t9O6-qn
mr 161. (MIRA 143M
1. Rizheki~ politekhnicheskiy ins+Atut.
(Indatclione) (Sulfonation)

T. T. LVAHAG
DWISS . G. Ta.
Nitration of 2-benzyl-1,3-indandiones. Zhur. ob. khim. 31
no.3:9n-915 Mr 161. (MIRA 14:3)
1. Institut organicheskogo sinteza AN latvi koy SSR&
(Indandione) (Nitrationr

FREYMANIS, Ya.F. [Freimanis, J.1; -.VANAG, G.Ya.
Baines of di- and polyketones. '-'*I~~iV-6s 2-Methyl-I., 3-Judary"one,
imine* Zhur.ob.khim. 31 no,,6:1945~-1953 Jo 161. (MIRA 14:6)
1. Institut organicheakogo sinteza AN Latviyokoy SSR.
(Indandione)

FREYWISY Ya.F. (Frelmanis, J.]; VANAGI GoYas
Imines of di- and polyketoneB. Part 7t Nitration of 2-methyl-1.,
3-indandione and of its imine. Zhur.ob.kbim. 31 no.6sl954-1962
is 161. - (MERA 14:6)
1, Institut organicheakogo sinteza AN Latviyokoy SSR,
(Indandione) (Nitration)

DjL G Ya. [Vanags, G. ]; OZOL., Ya..ra. [ Ozols, J.~-]
Reaction of 2-halo-2-methyl-10-indandlone with aromatic and
heterooyo3ic amines. Zhur.ob.khim. 32 no,,5tl436-11641 W 162.
(MIRA 15 s 5)
1. Institut organicheskogo sinteza, AN Latviyokoy SSR.
(Indandione) (Amins*z)

DREGERIS, Ya.Ya. [Dregeris,. J-1; VANAG, G.Ya. [Vanagsi, G.]
2-0-Aminoethyl-2-phenyl-I.,3-indandiones. Zhur.ob.kh" 32
no.9:2863-2867 S 162. (IMA 15:9)
1. Institut organichookogo sintoza All Latviyokoy SSR.
(Indandione)

UAGAT, R.A.; VANAG, G.Ya. [Vwiags, 0.]
Nitro- and chloronitrobindones. Zhur.ob.khim. 32
no.11:3627-3630 N 162. (MIRA 15:J1)
1, Institut orgenichookogo sintoza AN Latviyukoy SSR.
(Biridom)

AUTHORS:
MAyland, 0 Ta. VanaA
0 =
Academicia the
SSR
TITLE: Iodonium Derivatives of
Transformations
PERIODICALi Doklady Akademii nauk S3SR,
G - Ya
5102Y60113110410361073
tatviyeicaly-a
BO11 017
I
5-Fhenyleyelohexanedione-I 3 and Their
1960, Vol 131t Nr 4t PP 647-849 (USSR)
TEM. In an earlier paper (Ref 1) the authors produced a now compound from 5-phenyl-
oyolohexanedions-1,3: snolatebstainephen5-1-(5-phonyloyclohexanedione-1,3-yl-2)-
iodonium (I)t which In the following is referred to as phenyl iodonium. The authors
dealt with the study of its p-operties$ the structural characteristics, and its al-
kylation and cleavage products. It is a white substance soluble in chloroform
and benzene under intensive yellow coloring. Phenyl iodonium is not highly re-
sistant, and is cleft by various reagents, especially by sun rays. Cleavage may
proceed in two directions with the ruptare of the iodine-carbon bonds. Thust
phenyl iodonium decomposes smoothly, in the presence of EC19 into iodobenzene
and 2-chloro-5-phenyloyclohexanedione-lt3 (M- In pyridine solution and under
the action of temperaturep the following cleavage products are formed: iodoben-
zene and phenyl ether of 2-iodo-5-phenylcycloboxanedione-1,3 (III). In the pre-
sence of silver nitrate and pyridine, cleavage takes place only in the iodine-
phenyl bond; in this connection, the silver salt of 2-iodo-5-phenyle clohexane-
diogel~,3 (IV) is formed. By strong acylating and alkylating agents ~benzoyl
Car

lodonium Derivatives of 5-PhanYloYcloboxanedione-1,3 S/020160/13l/04/036/073
and Their Transformations BO11/BO17
chloride, triethyl-oxonium-boron fluoride), phenyl iodonium is not cleft but
formsacyl- and alkyl derivatives. As a consequence, the rupture of the iodine-
carbon bond is oriented as is the case in analogous dimedone derivatives (Ref. 2).
Under given conditions, phenyl iodonium exists without any doubt In the form
of the enolate anion. It follows therefrom that the electron density on the
carbon atom of the active methylene group is increased as compared with the
non-ionized form. The enolate anion system is characterized by a high mobility
of the electron charge. The(absorption spectra of phenyl iodonium (I) and of
pyridinium-enolate-betaine VII) show strong displacements of the character-
istio maxima of the enolate-anion system 6f the enolate betaines as compared
with a normal system. This may only be explained by a change in the electron
structure and a doubling of the bonds. It may be assumed that the electron
density on the carbon atom of the active methylene group increases under the
influence of a positively charged substituent. Hence, also the character of the
carbon-carbon and carbon-oxygen bonds in Ahe system is changed (see Scheme).
Up to nowo no satisfactory method has existed to determine the correct structure
of the enolate anions. The balance of the charge In both oxygen atoms may be
expressed, as to usually done, by dotted lines for non-integral bonds (e.g. IT).
In symmetric systems, the equivalence of the two carbonyl groups must be ob-
served. The authors, however, proved by their examples that the electron

Iodonium Derivatives of 5-Phenylcyclohexanedione-1,3 020/60/131/04/036/073
and Their Transformations B011/BO17
density in the oxygen- and the carbon atom may vary. In this case, charge por-
tions localized in indiviiual atoms can be difficultly estimated. For this reason,
difficulties arise in the preparation of enolate betaines. The hitherto used All"
method (VIII) is not sufficiently precise. Method (IX) (see Scheme) would be
the most correct one. The difficulty of estimating the charge portions 6 and 61,
as wall as the fact that 26 + 61 - I must also be taken into account. There are
5 Soviet references.
ASSOCIATION: Rizhskiy politekhnicheakiy institut
(Riga Polytechnic Institute)
SUBMITTED: October 15, 1959
Card 3/3

qqqq
AUTHORS: Neyland, 0. , Stradyn Is Ya., Vanagg G. S/020/60/131/05/028/069
Academician AS LatvSSR B011/B117
TITLE: On the Structure of Some Cyclic 2-Nitro-diketonesll,3
PERIODICAL: Doklady Akademii nauk SSSRO 1960, Vol 131, Nr 5, PP 1084-1087 (USSR)
TEXT: In continuation of their work on the tautomerism of the cyclic 2-nitro-
diketones (Refs 1, 2), the authors studied 2-nitro-dimedone (I. R 1 - R2 ~ CH39
see scheme), 2-nitro-5-phenyl cyclohexanedione-1,3 (2-nitrophenedione; I Ri = H,
R2 ' C6H5), their anions, and some related compounds. The structures of ihe
compounds mentioned as well as the difference between the three nitration
products of phenedione (melting point 120-1210, 131-1320, and 119-1200,
respectively) could be clarified. The infra-red spectra of the solid substances
were taken in suspension in paraffin oil and in chloroform solutions. The ultra-
violet spectra of 10-4 M solutions in H 20, CH3OH, or GHC1 3were taken. Polaro-
grams of 10-4 M aqueous solutions of the corresponding substances in buffer
solutions were taken by Britton-Robineon on a background consisting of 0.1 N M.
Table I shows the compilation of the results. From these, it follows that the
2-nit ro-dime done and the 2-nitrophenedione in chloroform show an analogous
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C q q q I
On the Structure of Some Cyclic 2-Nitro-diketones-1,3 S/020J60/131/05/028/069
B011/B117
structure, i.e. that of a nitro-enol in which a stable intramolecular hydrogen
bond has been. established for the hydroxyl group. The analogous structure of the
molecules of 2-nitro-dimedone and 2-nitrophenedione in chloroform is proved by
the similarity of their ultraviolet spectra. The infrared spectrum of solid
2-nitro-dimedone differs considerably from its spectrum in chloroform. Hence, it
follows that 2-nitro-dimedone in the solid state exists also in the form of a
nitro-enol. In this case, howeverp not the intramolecular, but the iLter-
molecular interaction of the groups prevails. On the other hand, the infrared
spectra of solid 2-nitrophenedione give evidence of the facts that'. 1) both
modifications with melting points of 131-1320 and 120-1210 have an analogous
structure, and 2) that the structure resembles in this case the state found in
a CHU solution. This means that this structure forms a nitro-enol with an
intramhecular hydrogen bond, though an intermolecular interaction can take
place in this case also. The third modification of the 2-nitrophenedione
(melting point 119-1200) has a quite diffnrent structure. The authors came to the
conclusion that this modification corresponds to the 6-nitro-3-phenyl hexanoic-5-
acid (IV). This acid forms when 2-nitrophenedione is boiled in aqueous solutions
whereby its ring is easily split. From the infra-red spectra of the solid
ammonium salts of the 2-nitro-dimedone and the 2-nitrophenedione, the authors
Card 2/3

6qqql
On the Structure of Some Cyclic 2-Nitro-diketones-1,3 S/020/60/131/05/028/069
BOI 1/-B1 17
conclude that a mesomeric anion (II) with the charge distributed between two
carbonyl groups and the nitro group must exist. It seems that the electron
density is unevenly distributed in -the mesomeric 2-nitro-enolate anions.
2-Nitro-dimedone and 2-nitrophenedione on the one and 2-nitro-indandione-1,3 on
the other hand have an entirely different structure. The two first-mentioned ones
are in the solid state nitro-enols, while the latter exists as a nitro-
diketone or as an ionized nitro-acid. This and other structural differences can
be explained, if it is borne in mind that the 2-nitro-dimedone and the 2-nitro-
phenedione have a stable six-membered ring, while there is a higher-stressed five-
membered ring in the 2-nitro-indandione-1,3. In the latter endocyclic double
bonds are less advantageous than the exocyclic ones (Ref 2~. Therefore, the
tendency of the 2-nitro-indandione-1,3 is to form a type of a keto-nitro-acid,
while, in the case of the six-membered nitro-p-diketones, the formation of a
nitro-enol is possible. A. Grinvalde and M. Tiltin' are mentioned. There are
1 table and 14 references, o oi wnich are Soviet.
ASSOCIATION: Institut organicheskogo sinteza Akademii nauk LatvSSR (Institute
of Organic Synthesis of the Academy of Sciences, Latviyska SSRT.
Rizhskiy politekhnicheskiy institut (Riga Polytechnic Institute)
SUBMITTED: November 23, 1959
Card 3/3

BC-090
S7,7 v o S/020/60/131/06/34/071'i
BOil/B005
AUTHORS: Neyland, 0. Ya.9 Vanag, G. Ya.9 Aoademicianv AS LatvSSR
TITLE: The Mechanism of Interaction of Plienyl,-I.odoso Compounds With
Some P-Diketones I
PERIODICAL: Doklady Akademii nauk SS311v 1960, Vol, 131, No. 6, pp~ 1351 - 1354
TEXT: The authors state that the reactions of phenyl-iodoso acetate can be di-.
vided into 2 subtypes: 1) on reaction with alcohols, a-glycols, and amines, 'Its
oxidizing properties become apparent. Ketones, azo- and other ocmpounds are
formed. 2) In the presence of strong acids~ reactions occur with aromatic hydro--
carbonsp and iodonium salts are formed. In reality, both types of reaction are
based on a common scheme: a) the mobile proton is separated, and the correspond-
ing derivative of bivalent iodine in fcrmed; b) the intermediate produ-~t decom-
poses, or is stabilized. This depends on the character of the new bond of iodirle
(with C,N,O) and the present anion. The reactions mentioned in the title and in--
vestigated by the authors are in full agreement with this mechanism. It is knowr
(Ref. 10) that dimedone with iodosobenzene and phenyl-iodoso fluoride forms an
Internal iodonium salt of the enolate-betaine type (11Ip R1 - R2 - CH3 ). When
Card 1/3

The Mechanism of Interaotion of Phenyl-io4oeo Compounds S/020/60/13'!/06/34/071
With Some P-Diketones BOli/BO05
the authors transferred this reaction to other P-diketonee and 0-keto eaters, it
appeared that no Lodonium compounds can be Isolated. This applies to acetyl
acetone, dibenzoyl methane, indanedione-1,3, 2-phenylindanedione-10, a:~,etoacatic
eater, and malonic-acid eater. lodobenzenelwas formed in all cases. IV and V
(2-acetoxy derivatives) were formed aa 2nd produots in the casi) of d4.brnz.-,yl
methane and phenylindanedione. The reaction of phenyl-~Sodoao acetate In the
presence of pyridine yielded enolate betaines of pyridinium-p-dirarbonyl com-
pounds (VI) in the case of acetoacetic --Aater, acetyl ant%tanp... and dlbenz~'.yl
methane* The reaction of phenyl-iodoso acetate with 0-dicarbonyl comp-_'unda give-Z'
a new proof of the double reactivity of the latter. Thia again shows the great
difference'between the properties of P-diketones of the cyclohexanedi-)ne-1,3
series and other groups investigated. The pyridinium-erolate be'aines (VI) aTle
yellow crystalline substances. Their melting point cannoT be ac-aurately deter-
mined. Some of them lower their melting point by absorbing air moisture
(Table 1). The structure of these substanc,~s was investigated by ultra'liolet
and infrared absorption speAra. Some of them ha-;-e a .As-form, others a trans-
form. The infrared spectra of the enolate betaines investigated in the range of
double bonds show a complicated picture which can be hardly interpreted at fir3t,
It can be saidq however, that the localization of the charge in the enolate-
Card 2/3

804019.)
The Mechanism of Interaction of Phenyl-iodoso Comp-w-unds B/020/60/13-,/06/34/07-'
With Some P.-Diketones BOII/BO05
anion systems greatly depends on structural factors. There are I table and
18 references~ 4 of which are Soviet.
ASSOCIATION; Rizhokiy politakhnicheakiy institut (Riga Polytechnic Instituts)
SUBMITTED: November 30,.1959
Card 3/3

80056
S78/00 S/020/60/132/01/30/064
B011IB126
ATJTHORSi Aren, A. K.9 Neyland 0. Ya., Vanag _G. Ya., Academician of the
A7S LatvBSR
TITLE: The Structure of 2-Para-Bitrophenylindandione:.1,3
PERIODICALs Doklady Akademii nauk SSSR, 1960, Vol. 132, No. It PP- 115-118
TEXTs The authors have shown that 2-para-nitrophenylindandione-1,3 (NPI) is a
very mobile systemp which exists in polar solvents and apparently also in the
solid state as an anion with a balanced electron structure. This system is also
capable of mutual conversions. In solveate of week polarity NPI exists in color-
less diketo form. The BPI anion possesses two kinds of reactivitys a) with diazo-
methane it forms a methyl eater of the enol form; b) with bromine and chlorine,
2-bromine and 2-chlorine derivatives are produced. NPI differs from the color-
less 2-phenyl indandione-1,3t since it is dark red In color The 2-chlorine
and 2-bromine derivatives of NPI are colorless, while the 2:amino derivatives
are yellow or orange. The authors-wanted to clarify the cause of this coloring of
NPI. Phenylindandiones crystallize from polar solvents as red substances. On the
determination of the melting points, the red forms become colorless. There are,
Card 1/3

80056
The Structure of 2-Para-Nitrophenvlindandione-1,3 S1020
,16011321011301064,~
B011/B126
however, signs that the red form of BPI is stable, and is not influenced either
by the action of temperature or by the type of solvent. In order to clarify the
possibility that BPI may exist in valence structures (III) and (IV), the authors
analyzed NPI and some of its derivatives in the ultraviolet and infrared.
Further, the methyl eater of its enol form G 16B110 4N was analyzed. Fig. 1 shows
that the ultraviolet absorption spectra of BPI and its Na salt have identical
curves. It is obvious that the electron structure of BPI in the solution is the
same as that of its anion. Therefore, BPI is dissociated in a solution of
absolute methanol. The ultraviolet spectrum of BPI gives an absorption curve in
dichloroethane which is characteristic of the diketo form (Fig. 2). The data of
the infrared spectrum of a saturated BPI solution in dichloroethane agree with
those of the ultraviolet spectra. 0.0001 M BPI solutions in dichloroethane are
completely colorless. After standing for a long time in chloroform or diohloro-
ethane a suspension of red BPI gradually changes to the colorless crystalline
form, which is without doubt a diketo form. During the separation from the
solution the colorless form changes back to the red form. Thus, contradictory
assertions are disproved (Ref, 7)- BPI differe from the other derivatives of
2-phenylindandione-1,3 which are replaced in the para-position by eleotrophilic
substituents, simply because the red form is more stable here. The ultraviolet
Card 2/3

80056
The Structure of 2-Para-Nitrophenylindandione-193 S/02 60~1321011301064
P B01 1YB12
spectrum of the methyl ester of the enol form of NPI in absolute methanol differs
considerably from that of XPI proper. Thus, the enol ester structure of the former
is confirmed. The infrared spectrum of red NPI suspended in paraffin oil, recrys-
tallized from glacial acetic acid, disproves the theory of its existence in di-
keto form (I), since no absorption of the CO groups occurs. When the sample is
dissolved in water and then recrystallizes, besides other oscillations, fre-
quencies of average intensity of the CO groups occur at 1700 and 1735 cm-'. The
authors believe that it undergoes a partial conversion to the diketo form under
the action of the solvent. The data of the infrared spectroscopic analysis do not
prove that the red form of solid NPI is an enol (II). The authors also refute the
previously assumed structure of diketo nitric acid (IV), on the basis of their
results. The infrared spectrum in the region of double bonds is so complicated
that one cannot really speak of characteristic frequencies of single groups
(Ref. 8). The authors illustrate the structure (VII) that they assume, in a scheme.
They thank A. Grinvallde and M. Tiltin'sh for taking the ultraviolet spectra.
There are 2 figures and 10 references, 6 of which are Soviet.
ASSOCIATIONt Rizhskiy politekhnicheskiy institut (Riga Polytechnic Institute)
SUBMITTED: January 30t 1960
Card 3/3

TANAG, G.Ta., almdemik; ZHAGLT, R.A.
Color reaction for bvdrazine and substancee wbIcb liberate
17drazine, Dokl.AN SSSR 1)3 no.2:362-363 Jl 160.
(XIU 13 3 ?)
1. !n9titut organichookogo sluteza Akademil nauk Latvivakoy
SSR. 2. Akademiya nank Latviyokoy SSR (for Vamg).
(Fydrazins)

GUN, B.Ta.g VANAG, G.Ta., akademik
4-Cyclohoptena-1,3-dione- DDk:l.AN SSSR 133 no-3:588-591
Jl 160. (MM 13:7)
1, Institut orgunicbeekogo sinteza Akademii nauk latvSSR.
2, Akademiya nauk LatySSR(for Tanag).
(Cyclohoptenedione)

BXMIKIY, M.L.; GMV4W, 3.1o; ARMI, A.K.; MAG, Mae, akademik
A new class of pharmacologically active substances with a well-
pronounced effect on the central nervous system. -Dokl." SSSR
134 no.1:217-220 S 160. (MIRA 13:8)
1. Institut organicheakogo sinteza Akademii nauk IatvSSR.
2. Akademiya nauk IatvSSR (for Vana6).
(IMUNDIOEZ) (PMMOGOIDGY.)

DUBUR, G.Ta.; VARAG, G.Ya., aklidemik
4z:.~
Intramolecular reversible cyclizatior. of the amides of 8-(21 3`- (00),
61 5'1(00)-dibenzoylonsp7ridyl-0-1-naphthoic a6id. Dokl. 1; SSSTI
134 no.611356-1359 0 16o. (MIRA 13:10)
1. Institut arganicheskogo sinteza Akademii nauk IlatvSSR. 2. AN
IatvSSa (for Vanag).
(Naphthoic acid) (cyclisation)

ZHAGAT., R.; STILI-DINI, Ya., GRINVALDE, A.; VAIWE, G., akadenik
Structure of bindone and its derivatives. Dokl. AN SSSH 135 n0-1:
77-80 N160. (mm 13:11)
1. AN Latviyskoy SSR (for Vanag). 2. Institut or.ganicheakogo
sintoza AN Latviyakoy SSR.
(Indandione)

AREN, A.K.; AREN, B.I., TAIW, G.Ya., akademik
Nev method of synthesizing 2-aryliden-1,3-indandiones. Dokl.
AN SSSR 135 n0.2:3209-322 N ,6o. (MIRA 13:11)
1. Rixhakiy politakhaicheekly institut.
(Ind&-adione)

AREN, A.K,; DREGERIS, Ya.Ya.; V~NAG, G.Ya., akadeaU
2- A-bydrozyetbyl--2-phenyl--Ip 3-indandione. DOkl.AN SSSR 137
no.5:nlO-= Ap 161o (MM 14:4)
1, Rizhskiy politek)mlcheokiyinatitut. 2. AN Latviyskoy SSR
(for Vanag). (indandione)

FREMMIS, Ya.F. [Freimanis, J.); VANAG, G.Ya. [Vanags, G.I. akademik
Imination of 2-substituted 1,3-irdandiones. Dokl. AN SSSR 139
no.1:128-130 JI 161. (MIRA 14:7)
1. Institut organicheskogo sinteza AWemii nauk Latviyokoy SSR.
2, AN Latviyskoy SSR (for Vanag).
(Indandione)

DUBUR, G.lfa. [Duburs, G.]; VANAG, G.Ya. [Vanags, G.]. akademik
o-(2p3(CO),6..6(CO)-dibensoyleneii3onicotino7lbenzoic acid. Dok-l.
AN S~SR 1-39 no.2t369-372 J1 161. (MIRA 14:7)
1. Institut organicheskogo sintoza AN Latviyskoy SSR. 2. AN
Iatviyukoy SSR (for Vanag).
Ohnzoic acid)

GMA, L.S.; VANAG, G.Ya., akademik
Heminal diindandionylalkanes. Dokj. AN SSSR 139 no.3:.597-600
jl.~61. (MIRA 14:7)
1. Institut organicbeskopo sinte7a AN LatvSSR. 2. AN LatvSSR
(for Vanag). (Indandione) (Paraffins)

VANAG, G.Ya. [Vanags, G.1, akademik
GREN, E.Ya.;
-
2-Phenyl-4,5,6,7-tetrahydro-1,3-indandione. D*I. &N SSSR 139
rv:~.4:866-869 Ag 161. (MIRA 14:7)
1. Institut organichesko 0 sfnteza AN Latvivskoy SSR. 2. AN
Latviyskoy SSR (for VanajT '
(Ind4ndime)

STANKEVICH, E.I.; VANAG, G.Ya. [Vanagoe-G.I, akademik
Asymmetric three-carbon condensations with 10-indandione. Dokl.
AN SSSR 140 no-3:607-6og s 161. (Yu-Ri~ 14:9)
1. InBtitut organicbeskogo sinteza AN Latviyskoy SS4. 2. AN
Latviyskoy SSW