SCIENTIFIC ABSTRACT BOGDANOV, S. V. - BOGDANOV, S. V.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R000205820019-4
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: June 9, 2000
• Sequence Number: 19
• Publication Date: December 31, 1967
• Content Type: SCIENCEAB

S/18 63100510031"0101046
B102YB180
AUTHOR - Bogdanov, S. V.
..TITLE: Experimental criterion of ferroolectricity
PERIODICAL: Pizika tverdogo tela, v- 5, no. 3, 1963, 811-818
TEXT: The author discusses the possibility of classifying ferroeleetrics
on the basis of specific experimental criteria. Two types are given
particular consideration, those with sharp and those with blurred phase
transitions. The latter were discovered by 0. A. Smolenskiy et al. (FTT
2, 2906, 1960) and show relaxative polarization in*a wide temperature
range. The phase transition (curie point or region) and spontaneous,
changeal:-le,polariiation are common to all ferroelectrics, but the nonpolar
(paraelectric) to polar (pyroelectric) phase transition may not be observed
with those displaying chemical transformations below the Curie point and,
while spontaneous polarization is characteristic of all pyroelectrics,
only the ability of changing the sign of P 8 being specific for
ferroelectrics. It is caused by an applied electric field and indicates
the presence of a domain structure which, in its turn, causes the
Card 1/3

5/181/63/005/003/018/C46
Experimental criterion of B102/B180
nonlinearity of P(E) and L(E). Ilerroelectrics can thus be characterizedg
below the Curie point, by: a) belonging to the class of pyroelectrics;
b~ having a domain structure which is c) changed by an electric field;
d hysteresis of F(E) with saturation, P 0 and Eor (the points of
intersection with the axes) being field-independent; e) nonlinear course
of,,_(E- Only 0) and d) are necessary and sufficient conditions, but
even fl is not reliable since saturation is often indistinct and ambiguous.
Ferroelectrics with blurred phase transition can be similarly characterizC4
but with a Curie range in which they show relaxative polarization, i. e.
the temperature maxima of F_ and tan J depend not only on the permanent
field but also on the variable field frequency, rising witha'. But not
even this is a necessary or sufficient condition for this class of
ferroelectrics. They can only be classified by the common properties
above, together with relaxative polarization, field dependence of the
temperature maxima and diffuseness of the structure-sensitive'.X-ray lines.
There are 2 figures.
card .2/3

5/1 81163100510031018IC46
Experimental criterion of B102/B180
ASSOCIATION: Pizicheskiy iAstitut im. P. N. Lebedeva AN SSSR, Moskva
(Physics Institute ime-ni P. N. Lebedev AS USSR; Moscow)
SUBMITTED; October 8, 1962
Card 3/3

L 18949-63 _Pfj(-j)1'9WP(q)j1VWT tDS tSCB) W UP::I/r Tf
_=2
(C)
S9D Pt-4 GG/JD
ACUSSION Nki AP3007316
9/0181/63/005/009/2703/2704
AUTHORt Bosdanov, So Ve; :Ransushin,, V, A,*,,Sinkha, Do K6 0
TITLEt Relaxation proportion of Be ningil
antimony impurities L~_03 81ngle e ryst.-Is contai
SOURCEIllizika tvardogo tela, v. 5, no. 9, 1961, 2703-2704
TOPIC TAGS: barium titanate relaxation property, single crystal
relaxation property, barium titanats single crystal., barium
tLtansto crystal property, barium titanate crystal, barium
titanate, relaxation property, barium tLtanate dielectric property
ABSTRACTt The dielectric constant an a functLont.of temperature
N
was investigated in barium titanate vLngle crystals7contaLnLng
Sb20, impurities. It was found that 1) the aLngle crystals of
barium tLtanate possess forroolectric and relaxation properties
for certain antLidony impurity concentratt.ona; 2) the LntroductLo.
1/2
Oki', IL

L 18949-63
ACCESSION NRi AP3007516
of antimony impurities lowers the Curie point, the affect being
well marked at antimony concentrations above 0.01 molZ; and 3) theli
appearance of a maximum on a curve of dielectric constant versus,
temperature indicates the presence of relaxation polarization in
that temperature region. Dependence of the dielectric constant~A
on temperature was also investigated for temperatures of 120-2,00ce,
Orig. art. has: 2 figures.
ASSOCIATIONt Fizicheskiy institut im. P. N. Lebedeva AN SSSR,
Moscow (Physics Institute AN SSSR)
SUBMITTEDt 06Dec62 DATE ACQt 140ct63 ENCL: 00
SUB CODHt PH
NO'REF SOVt 001
OTHER: 001
Cord_22

XISELEVA, X.V.; BOGDANOV, S.V.
.- 1
Structure of solid solution of SrT103-Bi2P3 - 3TiO2. Fiz. tver.
tela 5 no.110133-3137 N 163. (KRA 16:12)
1. Fizicheskiy institut imeni P.N.Lebedeva AN SSSR, Moskva.

BOGDANOV, S.V.
Dielectric properties of strontium bismuth titanates. Fiz. tvar. tola
5 no.120390-3396 D 163. (MIRA 17:2)
1. Fizicheskiy institut imeni Lebadeva AN SSSR, Moskva.

BOGDANOTI, S.Y.- SHIBRYAYBYR, L.S.
Hydraxy derivativei of-phaziantbrone. Part 3; 1,2-phonanthrons-
quinoneQ.4mim, and *3-;4-phinathronequlnone-3-=ime. Zlw. ob.
kb,im. 33 no.5;1529-15~2 My 163. (MIRA 3.6--6)
1. Nauchno-iseledovateliskiy institut organichookikh polupro-
duktov i kraoitelay.
(Phenanthronequinons) (Oxims)

BOP4ANPYAJ. V. t SHIBRYAYEV*, Le S.
Hydrmq derivatives -;at phenanthrene. Part 41 Bisulfite empounds
of 41-sulfonophemylsm-2- and -3-phenantbrole. Zhur. ob. khim.
33 no.521532-1536 -W '63* (MIRA 16:6)
1. Nauabno-ionledovatellskiy institut organichaskikh polupr6.-
duktovA 1krasitelat
(-Unanthrol) (Aso dyea)

BOGDANOV. S.V.; SHIBRYAYEVA, L.S.
- - --l ~-
PqdroV derivatives of phenanthrene. Part 51
9.10-Phenanthrenequinone-1,2--furazm,i and products of its reduction.
Zhur.ob.khim. 33 no.6tl978-1979 Je 163. (MM 16-.7)
1. Nauchno-isaledovatellskiy institut organicheskikh poluproduktov
i krasiteley.
(Phenanthrenequinone) (Purazan)

BOGDANOV, S.V.; RASSUSHIN, V.A.; SINKHA, D.K.
Relaxation properties of BaT103 single crystals containing antimony.
Fiz. tver tela 5 no.9t2703-2704 S 16). (MIRA 16t10)
1. Fizicheskiy institut im. P.N.Lebedeva AN SSSR, Moskva.
.A*

ol-..- -, -;-',
. . - 11
- " -., '. ~ , ; ~:-g .
'~.,.~oii ~

ACCESSION NR: AP4036635 S/0048/64/028/004/0636/0642
AU771OR: Bogdanov, S.V.; Kisetleva, X.V,.
TITLE: On the nature of tho dielectric properties of SrTiO3'Bi2O3'3TiO2 splid solu-
tions Zfteport, Symposium on'Ferromagnetism and Forroolectricity hold in Leningrad
30 May to 5 Juno 19627
SOURCE: AN SSSR. Izv.Ser.fiz., v.28, no.4, 1964, 636-642
TOPIC TAGS: dielectric relaxation, strontium titanate solid solution, bismuth tita-
nate solid solution
ABSTRACT: Solid solutions of'up to 9.6% bismuth titanate'in strontium titanate were
examined by x-ray diffraction at room temperature and liquid nitrogen temperature in
search for indications of it phase transition. The investigation was undertaken be-
cause of the great difficulties (discussed at some length) encountered in attempting
to explain the dielectric relaxation observed in these materials as an effect of a
diffuse ferroelectric phase transition, Although the resolution was sufficient to
separate structure sensitive lines with a tetrahedral distortion of 0.0011 ora mono-
clinic or rhombohedral distortion of three minutes of arc, and distortions of one--
Card 1/3

ACCESSION HR: AP4030035
sixth these values could'be detected by variations of line width, no deviations fro;
the cubic structure were found. After a further discussion of the difficulties of
accounting for the behavior of these materials in a more conventional way, it iscai-
eluded that thoy are representatives of a now class of substances having proportias
intermediate between thoso of true forroolectric materials , and materials showing
classic ionic relaxation. The following postulates are adduced to explain the di-
electric relaxation of the strontium-titanate-bismuth titanate solutions: 1) The
dielectric relaxation is clue to relaxation of titanium ions within the oxygen octa-
hedra that are distorted by proximity to defects. 2) Vie concentration of the relax-
.ing quasidipoles is large. 3) The activation energy and dipole moment of a relaxing
quasidipole depends on ita distance from a defect. 4) The activation energies of the
.quasidipoles are asymmetrically distributed. The consequences of these postulates
are developed, and it is shown (with the aid of plausible assumptions concerning the
leffects of the dipole-dipale interactions) that they can account for the behavior of
,the solid solutions. Orig.art.has: 3 figures and 2 tables.
Card 2/3

-ACCESSION NRt AP4030635
~SSOCIATIOM: Fixicheakiy Lnatitut i*,P,.X,Lebadeva Alcadenii mAuk SSSR (Physical Ine-
titute, Acadamy of Sciences, SSSR)
DATE ACQt 3DApr64 ENCL.. 00
SUBMITXZD: 00
~iatm ocoll XR MW Mi 011 MWIRS 000
card3/3

TIS-E
4
,tbL_jj,j_Uhion
mp 5-5
SCUR'AE:
L
ON IM; AFSQ16='_-~ mvom/65/0,59/006/0896/0900
'K V
n0V_
iA *9
13
Concerning phase transitions in qtrontiim t! tMiate Dort,
---TZ-q tov-on- ~he -Don
Conference on FerroelectricTty. at
AN SSSR. :Ezvestiya.Ser.fizicheslcayatv.29v no-6, 1965,896-900
TOPIC TAGS: single crystal, phase transition, x ray diffractions
dl,,ulle refraction, dielectric constant, strontium compound, titar,-5te
-ABS"R-ACT: The authors have measured the birefrLing-3-nce and dieleRctrb
cizigle c-17-qtPLIS El- temnperat~_res "!--oa 4.-'7T,_0_7_K0_0, K
Zn"'R' 7M'"~e examined the diffraction of Fe x-rays by the crystals In or-
der to determine the "presence and possible nature of phase transitiats
in this region. The crystals were grown by the Velnouil technique.
I - )1-obably to
Abcve 1120K the double refraction vas small and :.
.-ti-atns. Between 112 and 3-100K the initial &nisc*':-ony Of the cry-stall
coripletely disappeared and the double refraCtiCIT) Di'~gTIT, tO 11'i3e 11-aDid-

L 57035-651-
th e-lect-ron
a
V47a O~u -
Magn 0 resontMOW`ZOth6d- 1. o4ouv e-retrac' --c"ased
at.
VIM decreist 'W' 0 tmad~levained apprq;dmately.ccns7
random. fluctVatiohs 7he ~h ..Umd, In: the double refraction curve at"
arp. t ~', .. ~ - - ., . - ~ - ; *
-presence of & second phase transitdon, In agreement
60 K indicatet the:
--S Xtb-tad-l F-W Ly-tlej, R.W.-Moos and E.B.Moore (B.131
vith findings of R
Amer. Phys.-Soc.8,417; 'r96-31-S --Its a
W1, -is,sugg stedthat the fluctuations belcw.. .
EDO:Rre-due- to A Passa.tM91tion; the prasence of this transi-i
tion is also in agreementvith the results of Krogstad et al. X-ray
~.diffxactiqn profiles.. measured.. at :779K could not be explained by the 1
'al trad
ragon s twe It ism, concluded that the
64 -tet
~;atru,cture i
5 ps thl~'Aha- lattice -'zonstahl S
~x Pr6files, !at r0=
b- vw~Z
U~~iqvwll,xhcmibobedral distortion of the unit oubs~
temperaturb revealed
amomtlng to t;4o m1nutes-of aree It is mMested that this distortion,
may be due to the fact that the crystals were 11rown at 200ODCa Mie Dir.
3.-

'goo -
i
~/O /09241
DemeshIMS, A.I. BI
...................
~TJTJZ.
Tibrati6nkI.SP'-8etra Of'stroutium, barium md calcium titin-
-geport.9 4th,'AllrUbdon uOI an Ferroelectricity held in 1
,a -as
Rostov-on-the-Don'12-15 vap-C-1116Y
wavnclgtx~ AN -6-SSR xvestlya*~_ it
at _-cF*wta3.j, -barium- titanatej- calcium-Imorgaidd
-go e rid
Con IM R
PO d sUBE, lum Tlxanaze, absorption spectrum, dielectric cons
tant# -FeFqv3]dtq vtructure.,~_.
-ABSVikT:-_.I- MeAnfr --reflectiow spectra- -of' GaIn
aM Ommission. anet
'Were ddm M& Vith- I the analogous spectra of SrTIO.3
And are,~Compax.
:end Ba!UOS -'_reporte&:.- -A _b -.1he 4uthors -and by: others. -Mie'covipar
ea ler , y comp"
of 5
IS intOrl3i t: -ail -th"e wMerials have the perovstite
S ructure but vith different symmetries at room temperature* The
CaTi%- t:ftnftilisiah s~ectrw las a doubLat vith the minimm near 30
MI and th6l_nn~aetieh speetrm haii sharper minim than those of;
F~
LN

V 57026" 6*.5,-'
q
A
r.T1OZ__znd ant of, CaTIO
Tip-3
in O-g- naitio M_- fi:o-:-delibri previou-sly btvc o*-.,
b
Cal
Fizi
the authors tverdogo tela 6,182,1964). It was found %at the de~~
generacy is tartly removed in CaTiO
3 and seven resonances were founds
between 17.9 and 87 microns. 'Cho diOlectric er,,Wtants of x
p jell thre__"
material,s were measured at f14)quencies from 100 to 3 X 1(~114 cycle/sm
The die 1%+ric constants -of SM03 and CaT103 remained unchan,,,,,ed to
abou," fin,cycle/soc and-were dete=ined entirely by lattice vib--a-
ti,on;. Additional dielectric dispersion vas observed in BaTiO,3 near
103-0 cycle/see; this Is ascribecl to donein wall relaxation. Mie con-,.!
tributions of infrared resonance Absorlition to the dielectric losses,,
of the three materials,ver2 calculatedo Mae dielectric losses of
S-rTICZ and CaTiO3 near :LOW cycle/see axe due entirely to lattice vl..~!
brationsa 7he dispersion equation for Ahe complex dielectric constant
of a cubic cMta3. with the pBrovaldte structure was derived by -;.he
method of _Wicochran (AdviftsO,3117 '? 3-1960) In an atteqpt to elucidats
the anomalously high Oseulatov Strengib of the lov fraquency mzmal
vibration, It Is cencluded that the hilli eseMater strei~th_ is aue
C a

61- 0-
ACGWION NE:

Origq~~tohas 4 form" -,15: gigures Wd3Uble s

WL: 00
SUMMED ~~-Oo

M-
0
.

W-
.

'CIW04IV65/029/006/0994/0998:
AU 011.,
~qsebqvaLKX. MM;sonashvili,B.N.;
V
_gdanb
,V.A.; Sent
Wff M;Rx.
n -iD
T.M
ac dping', -with n -50me physical properties of
ff
iti;a; , t'9 Pnv% e on
bar, eal .,..,-,Ort,.4th All-Union Conferena
'o 1 :4~7
-Ferroelectricity:- e1
][71 Stov the-Dcn 12-18 SeDt
SOURCE: AN SSSII.Xzvestiya.Ser.fizicYLeska~,a, v.29, no.6, 1965, 994-998
:TOPIC: TAGS:* fe ro ristlaf"biriu~t titanate,' doping, iron,
r electric ..C~
crystal s.tmcture anst
jphase,tr tion, dielectric constant, electric
conductivity optic abOontion
ABSTRA -Z6 iikthb- the Idetric eonstant,,:'elec-
CT; Aie
e~ c.T7s--
triLnsiiissloi~ of BaTiO3 singl
tals~-conteinihg up to:~ 6- at F,6~9 and have.,investigated the St ructAire,
of the: or~stalW b -d fffthioh At room temperature the stmic-
Wre -o;C . crystals.- YUalreaInyin -fxOIIi-O445.'to--Z*6 at4,7.,' rie-wa~; tetraeonal;-
a fw%,n+jniv-4-A& mn'ri'6- +hn" 0- A 'rat- -cf- 7M.1 WA'PA rnihl r% rkyul -hhal 7, 1 D i--

--4
)AMP WIPAP (b)/EWA( -Pt-71/Pl
P
APSC11613*9
j-4
AUTHOR., Bogdrunov, S.V.! Rassushin, V.A.
'0'
TTTLE: RegardLngj the mec ism Of appe ce of relaxational --olari-
Re Lyhe ToffisoLcayefr"
zation in bariuni-l"titanat ino'le crmtals~, d with
: oTe
n ium itan t
4th All- on (omn rro i.it---held in Rostov-on- Kn
Un Fon C_ (M_7e OVO 2;r
Y
A
,q
r&~~... AN SSSR.1--vestiya.Ser.fiziolieskayatv.M,no-6,1965,999-lmO
raw barium titaaate, dsping, t-ntimony,
TOPM TAGS:
'ASTRACT: 2he authors and 6*3-ldboretors have previously shown that
the dielectric constant of BaTiO,3 single crystals contai-nine, 0.3
tc 0.6 atet Bb iS fre-qumcy dependent -at wel I nrv-jv;:i r-he
Curiepoint and do 9 not follow the Curie-Wels.,i Im
tela 5,No.9,27M,1963; Kris tallograftya 10,74,1965). in orde-- tc I-"e_
termine whether the relaxational pol&rization thus revealead is due ~0
smiftee barriers at the electrode contacts as was sho, "I.P.Dogo-
by
Icard
V

Z`f-L' 57-r-61;;65'7-
ACGESSION NR: AP5O161Z9
Toditskiy and L. V. Sminio v (Piz,, tverdoco tela 4,3418,1962) to be the
case for rutile, or to polarization of microinhomogenieties dIgtribu-
tad throughout the volume of the crystal as dismissim by
N.A.Terhune (CerEmic Age 62,2,Z3,1953), the
tie further measurements reDorted here. The
S',,) dopeed BaTiQ3 crystals of different thiclinesses we:li~t
tomperatures from 20 to 2700C and at frequencie!; n,-, .-A
cycle/sec. By treating the sample as c)nqist-JLnF
ii, seriess of which tvo represent the :;urface
sEnts the volume effect,the authors coiiclude tn-
city wil-1 be inversely proportional to the
it is dus to volume effects and that it. will be 1-nder-c-rinent of'
thickness if it is due to surface effects. The
that the capacity vas approximately inversely proportion-a-I t n
thLcknesg at-"mperatures well below the Curie pr,',n,- an-, jE!
a~woe approximatel independent of thickness at UrMupera"~U-res
~ far a,-,CrVC-
th~~ Curie Wint.
t is concluded that tte redaXatlic-p-
Is a volume ef.Le-ct at lo-4 temperstux-as 5.nd F"

ACCESSION NR: AP50161,39
tmperaturzs. In th4e, narrow temperature range frDm 100 to 1.00*G the
-dependent than at t
capacity %I 6j-_j,, less
perat-ares on either side of this rarge. It i8 slaggeSted that =B
t -may be due to the p7asence In BaTiO3 of a slarface la"r In which the
gber than In the body of tha, cryst-*'
i;u.rle point is aamewhat hi
Drig.artohas; I f1guree
ISSOCIASIM. none
13MMITTED: 00 ENCLi 00 SUB CODE., 88
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(11) ha IM kelot lam (M). I is Wrivated to l.%4-C,J1*1,NJIj(OH)SOsH ~416
by boiling: with NaRS06. by treatting -M-s% (sauiger. aff. 27. 23(IW4)). or

by Zoo dust In N%SCN (Vannutlper. Diss.. Mormich 1012). T1w mechanism of inch a
convellosim of I to IV is Da tonstolle clear b
th
ti
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b
i
i -
00
06
at reac
ons. an
s
are
nvest
y
cawl
by beating pure I In water with SuC16 In HCl (or Zu dust and NHO);
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of the sulfoolk Wd th
ti
M .
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.
q
is caused by 1.6 M combined with U as 1) and
N&HSO
used is Um
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U e su
otoa
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000
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Y
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vet
ex*W the tat
lo
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b
oo
o
u
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C
C
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o
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VbYtaulmnerkmaffanxrntcnt.amamaun3ed. (Lants and Minglawam. C',A.
in the detu. of the presence of doe CO group In the tautonortic form V1 11 the actim all
M11.011. 110 on L there was Prioduced not 1.2
4-romplithoquinone dioxime-NaHS0
but
,
1
(VU) (altrowNevile-Winter acid) with a good yield
(pat. xpplicoit~m No. 6#.470(1M)). This reactiou proves again that the N*HS% .90
g"C;Z in I is in po"itlost 4. L It the Ismerk nit
t
D
o then the docrim at aw-CjsHi(-NOM
VM roosomplithols react with 14&11,90~%.milady

!O) will be represented by the tortnulsts

odM&ru1th;wcaja,O-Cljf4 :0)(:NOH)byX&ndU. Baltilitr(Le)obtained
1.Z4-CioHs(O10(NHJSO#H by beating w.0-C,~Hi(O1i)NQ with NOISOt, which corre, zo
with the forooloodout I and RL %lormhUov (C. A. 10. 2W: 11. =) zbowed
t I as btW &w dyes react with N&IISO. In the quinout-hydrossone form. and he
ef":f if: that the addo. of NaHS04 takes place at the CO group, Of these am dyes
MIT tbooft react with N&HSO. which have the am somupin the 1-pIsition and the
toga
'i Afa SLA &VULLVOWCAL LffjolAyvag CLAIWKATIOP
441
r- -4-9 -1 1
U Is AW a it x a K a it it of
w I V it a
0 t 0 0 0 0 0 0 0 0 0 0 0
cui i;.' III
-j T ja in A It tW 0 a a I N 13 0 3 2
n t 1K4
go 0 0 a
0
4 a 0
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00
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00
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69
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116
= In Um 21mvitim or do am voup In tbe -ipaisLm and the FTO group in 00
1
the Immisive. volciletbase with the Sam Voup in the 3 poshUm oknil the 110 group in the so
I-pod" do no inct with N&HSO, these conditims twing snakgous to nitrumo. *0
amplithols, The dzuetwe of the bbuWte cacapdo. o(aso (two diffm I"m V (mly by
the substitutlim of :NNIIAr for:NOII, mapreint W - t--N&LVsW1.). on PnA-wd 00
Colic C(- NOH) - C' PH)OSMA CcIf&.C(:N0II).C0II Colic. Q: Noll). CO 00
I I I 1 00
.3%(S(hN&)-CIl

M (VI) of

Cjf..C(.N0H).CHSObNa CJ14 - C(: N01i) - CIASOIN& 00
0 *
00
RX) 00
Colic. CO. C:NOH Colic, CO. CWHO11 0
&I(SO.N&JIl 00
M (XI) 90
bratins with N&HSOL is VW Into CJUNH#)SObH md IV (Buchmr wW Stickel. 00
C. A. M 195) by an&Wy with L In the conversim al naphthols into maphthylamincs go
by bestiow with NH*HSOc the intermediate products in-re canoeived by Bueben:r as
60
--' ic estitra; this was disproved by Vonxbtm&v (C. A. 12. 3374) who showed that
bk-b h
th
f
dd
f N
HSQ
t
d th
dfit
th
l
t
ib
k
t
bi
t 00
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*
o w
e axr
e
e s
ey are
e proc
e
e
n
#
ture. V. and Kamtkin (C. A. 33, 2433) isr"ted such it ptWuct of addo. of I mA. 90
NSHM to 2.I-CjJi#(OH)B%N& (Toblas &64. while Fuchs (C. A. 16.2950: 21. -MM)
epd. Um bisulfius of IA., 1.4.. 1.& and 2's-C111140M Thus. ,, ins to V.. 00
sluchem's rr*cdm may be (omulated in the csse ~( the convemon of 0- 00
CiollvOll to 0-CiolliNfl, u fuDows: O-CsllOll -*- C.H..CH..CO.CH:CH +
L, j 00
NHJJSO, P C.H.-CH,-C(0HX0S0~MI.) CH:CH -,- Nils - 1110
00
00
o:
6". *10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 e 0 0 0 # a a o 0 0 o * o o o s 0 0
00#440009 909069 0 9 fee* 0 see of go-qq-gooo*oo:::::0104

m Is IF a 111 4 at 42 111 At 0 m
*-.A A -9. L, -A k -11 -1. _0 --A.. --rAloo
A ... ... ...
::.A Calls Clio. C(Nits)(08(hNift). CIA t Of V. llaws Ow
00 g reaedviq Of naphthols in the ktto form on the hypothesis of Thirk-: formula RU for
#-CjjijOH and IM Ice &Cjjl1jOlI
00 0-
004 .00
(ZIU)
=00
Goo In the URW tarpe-st tatiou of mmophtholaa (and CoJW them am available 4 partial Vsku- r
cies, while In that of the ktto tam O-CAvOll has 3 and er-CasHfOH has 2 partial .00
04 walencles, and from tM greater satu. of the keto form V. concludes the possibility of
their tomation. The adda. of N*119(); to the CO group of the lortmes and aldebytko
:Vw must take p1moce at the cost of the partial valartic4cs of the C and 0 thus: ? too
09%
of the CO gmp In the above keto funns of naphthols is found the bimic
In the stmdure
differcum from the usaud keto stoup. tit.. the absence of the Inv, partial vakncy at the 0 411
C bearing the 0. A free partial vakney in the same nucleus is present only at the c
in the ard position [man the C of the CO. f.9, at the 4-C in O-C%JivOH and at the3.c in will a
wCtilvoli. Thus the maddis. of NOISOo to naphthols may toe represented by the '00
eel lumulas VV and XV sod nut by XW aunt ZVII%
D.~ '60
:a;
.1111o.,
db e1 4W iit
r-w too
u Is At 031 111: ~i 11 i
a at At a I Plan IrMILWA il~zlk
e 0 * 0 0 0 * 0 6 6 0 * 0 so 04 0400 of 0 so o 0
~00 9 0 0 0 00 0000 00*4 oilli a 000 0000 00 0 04 4 6 0 0 9i

04 114,411 AK I to him. I =W#) %INXO?41e)Av
t (41ile(C.
IX); this nitrated love In PW I am N)
A
R
(XI

so c
.
ectiuw,
,
the strurturel WONCOOMWWly Proved by It, It Jr4hvwj that the C4114 .attvull In tx cautu.4
I
I
l
th
lli
b
be

00 w
n
nnf
e "
. as th
k taktit %lit Ivy the Ac=IP.
ul nitration tA IX Is Consul it canakh"ble suit. of twf Muvvk. as a rt%ult of %plilting off *0
4 t1w Acin-up. th"t1oft the Cato group in the amber mulk (and inn) Alto cannot IM In
i
i 96

00 Iviasl
m
. a., In the jfv-positim to the MrO group. Thus; is left the only possible
V
structure
M with The C411o group In the poddati 4. &W I.3A2A-C.HMV(OkIr)-
(Chle
)(NM (11) for th
a
b
k
"
I 00
90 i
e
m
er mus
~
in new
mmula nudirs clear why amber
muAlvoklalovat than V% and evirlitimi without controdkikin the IVIKINS 44 the V"wk of 14 so

*0 ,
andC. The rxpW date fid~ Rutit"t the =mrd limmulas. weVirts4wownitratr4livy
th
IMi
l M M
l
l
d K
09
e "W
a
an
t
an
44h and Klwt usky am) joequsut (V .4-3. thr. isumt f

0
I.S.4cellawl OIONI IM) was P"vd, Ivy ettsm Mon.. and cx%nv"td with t,,
1~011) (Reiteverl. 1fer. 31. NVIRM)
Floth" and Risvid
tier 0

110
06 .
.
.
3 193
K
W
A
"
d
Wat' ".); Z111 was ""e"d tn 0.4-C.ItAl,
Y
AT
(ON I
21NI &
1
N I
4 to

of F
1O
&
ndftn
r
s f
vr
ft
d
t Sendeneyrt rattluxi lit 1,3,4 -C-I Islilef ONIr III#
)
MV). A pan of XV treated with CO
In M
t)
v
VI

00 #
e
go
e (Z
1
,1 with f0till's Me ether of hotivessallrylle "1 (11&' 12 flu- bulk
44 XV was "4kh, 6.1, h1to the All "Mil"I. In Mill aud torat"I 1*1th kft- [lull#
u
%to
( 0 0

00 v
c
Its
l
If hle"timl with that obtaiurd by the thin isht-st uitratrd x.v,,
light Yellow pitittswith strong musk odor, tn. OV, whick Weed with vwiuus sawl4es A 0
cam. ambrr mtmk. shouved roe depretailon of them. p. nis that
the 1-Itut-tury tv! 11 Is VU1 and that of ambee mush Is X1. It alsti follinsi that the t,-o- 00
00 figntal" al Ws prisihs" clitained trim" It Ivy the acklutt ut AcCl aud AWI. k 1,3.4.11 00

00 114 and that of Its (-Ot--t
ot I.AA.4 (W ItMe(NOD OKIrXCKIt0A%: MIX). U which XVIII t%
1
vv~*
wiviahk lwvauw In 111 6
h 0*
00

00 1
e NC
t
4 Stutt
even IvAllons 12-. 4- at M, In adda. to amber n;
Ibr nduct of nitration W V1. It *rA P. WeIrd &W
N
N

111
00 il-
W. ul, 91-2'. OW h*t%yWP#-bvtty1-"u1mat. ( )
t I
.
lit, Wis. which Is the IMUOVA-vil "0161 thymottuluorte unit rt-ormbles It In every wav
00
040 The formation of by-prodiarttiftends on the conditions &4 n1tratkm and "wrists u"1.
1,1
l
f Ma
ff
h 00
ow a
w format
ects t
9u o
e ykM of amber musit: and Impaitts to it a disagrtraW

90
IV 1~
0 0
0
9 00
0
0 0 000 a 0 a 0 0 0 4D
0

i ~ a
"P D)ib if 2p1611 loll 111) us UW 3630110
011111killm"lls
r -1 06) "Sao
A v-L- 1_1' AA so Cc 9V U41 1 4
p a It-
It- A" 1W, u-i't4v

00 t cold IntreisIvvIy colorril sect. fib* tit itive" IWCaltW 44 the ft*MathM it( ollolillito %itil 44
7 -410
quiraviold chmader (tlcvk" and SaImIlla, J, Rxjj, j1hys .1
". &-f 13. 71M. 1_17. jkut
-
If
(K IMM
h
K
3
,.
c
ttimitt.
v.
~
4.
I Eli*)
Inth
it
il
tiXth

*16 8
1. .
ro
ocia
m
"r
always slolvelu"t all kttcuw Wor coloratim a( the kukt ult;cb on beating tw dits ckanSV4
'
0 to nil I
lle ct*wvd IwWurt was iwitated ivilk IICI(% am the ;vIvithitair In italk Isluo

00 1 ctrOv.14 Mott aud C. A. 14, I=):
calf
Nic -leSMANItIC10
C?
) O
AllA which treated with w
iv
r
th
t
" At
o1
(M

0 -
.
r
4
a
e
es
r
r
e
g
'j
MtICKANOO clillaWle(CM" 0 MUI) (Kelitillano al"I IITTkrf, 1. 4, 1)~ slut
S
I
l b
k
fi
1
li
M111A.
.C.)
uffed with
l
lAlvWNbdvcv"qxlAmtoXXl Rml 2.4.XNfr(NItO)-
In Nv
virld hoon Wmty SMI VI b
l
thC M
HH
1l
f Ck
ZU)
l
N
t 1
C
A
O
,
f
1&n f
at
~r
y
,
.
Imij lorOrts"i ether at I I x W4,
-101. m 23 4* lln&224*; (b)NA1 g. yield Ix C21249.

W ad" to a nilat. of 2 PS, Mg shavilip and a "tal of I lit Ove. alks. M.o. therv tAux"I

00 W
::; '01 udia. in a water lath. pouted off (roul the 11111rartril Mir, 111A S. Ifil-111111t O"Idrit. the 0

it
: inist. m)k-4 with kv walff. vrbrftl)y lit 2 min. a irkilent irmictloet set lit with torntal6m i4
I it plit, the retwiloil was caul,irted 17 friluxIng 2 Mi. lit a willer [will allow"I 14) almoul
q
'l-rillight, Own "Impti. with kv. I ir tther likyrt orlid. %*4ird imilih ~Ao )If 4ttl"I 14 lilt
m

o 0
VaCl. thr VIA) rxiiirtled slid di3td. to
antIvIll NOV., 4%
'
ow 21-V (
5-4
1
I
d
RthVM
23
t
%
iv
%
.
,pt.
j7fd,:Zt
10
1all
d
(W
111
ld
h
4 W
f
Xill
b
f
A I
h
e
0
.
onm
~
- ~
.t. .
. g.
. lit.
n S.
t
e pow
.
u,
.
'
Na wlt -9 Kill (dtkd at 106
) Wld 82 CCL W*SAX Ill 23cv. of 14&Ntc ws rellm-1 2 hm at
10* I
1 RV
s alivill lath
th
dild
ith 10
Oll
N
l
i
t
d
V
t
-
en
. w
o
. slu
.
. arpi
ill m(SO XI
d
d
%
. N,
"
14
It%,*
to tr
wh
-
14TI'Ll
icM
n Ul
A
I 11(71
4
i
l
1d
d
t
4
0
j T
4 .
-
e
VOCA
.
m C
T
oll
wm
v vu
r
.
to l
It "l
t'l .
,
v
~
no*
00
00
'V"
04P. ~*.-v A
-
11
. :I 1 4
;- 7-
S
7

o
.
m
1 a two x 6.1w 819di
P
TT -

ill Ua at 00 u1, -
MD&Pwdg adcoliff Mal a Is 49 KO n I
0 00 0

0
0 ~
: : o & * 0 0 0 q 0 # o 0 0 0
0 o
000000000 0 a 0 0 :1411 4 0 0 0 0 0 lot o * 0

'06--04
*

4.4 to c 2111 a=. VI- 61,d So- thorn heated I hr. In a walror hooth. IM11 Na(ill it,
~
"M IV. 1160 td. '
'b draw, PiAd. with MO. dried still Kolf, the lct,o)
roctIrd.auddistd. in m(sul; tileplia-mlekdeempd.ost Il*-9*. XV,I,., 107 P*. PfrPd
i
34 8
M
ld
t
f 32
O
t

90 n
"
wn a m
l
o
x. (
1. on 0. Nalir, M g Cii shaving, and
%j O
UA
IIA)
In INS tv
tit NO wo holl
111 min
(m%
d
th
n
s
li
l
d
ti
l
00

0 .
torit
.
e
i
o
m
wi
r
ti o
,
ii.
J
1~
'
)U was sm
In a thin str
am to th
t
d t
iln
it
a
il
I I h
M t
d
0 e
oor
m
uit"
tor
tb *lan
4
e
."f.
. tr
r. m
, 41.0
00 nighLatesons-alloot(Leittol with JRtA). w&AM with &q. NAOIL W14, dried Witt, CA(lo- tile 0#
00 VtO expclkd. atioll twkv mildd, in mormis. XVI, Ht. IM 4% obtioluml in 2 x. Orld when .00
so the mil conlrod. frm% 7 3 jl~ xv. 0,0 K. 161C abotivirop slid L"N m VLO vrrrr treated 3 hrit,
ith anhyd. c(lo. then the Pilot, th'"movild, with Im and US iv~ ol 15% 110. riot.l. will% to
be the IR1.0 dittol, tiff. the midur Allossicti Well with KxoCtss. the hisol. part vittil with
M.O 00
00 .
the alk. eAn. in$& KM to C 1, and tircrystil. floon hill floss.
fute" oil
Iftso.
5"
wime with
l
d d

0

04 zr
rop
was IM
gd. when 3.1 a. a I. AcvO at -
ft
j.
It. u 8"'. f
exid. with Mots
outed on kv
was
the milt
d 151) th
C
I

,
.
.
en
.
p
N
3
2
Sixitation with 3. X I
~ (
in ist(w
tile fraction
distil
On Ht
O eipolled
k6f;~Rh &CI
01
N
0
00 .
.
.
s
v,
46
MONA with sq.
s~
I", I "Oll 04". was Illotsiolml In 111 j. of hot ate., ppill. a voilo. of 21 of crylitalm. whirti
1 21
d
r 00
ton
. platro .
"t-tv morlid, by sitting and msy tot. wpotrattly front ale.. pro.bo.
101 . 111.1a As, was oblabuil in 45; v6-I-I1-YPAhb',x'~ho1l8
sit
%. Ilow nivil" tot IV *0
.
,
IIN(N(d. so
00 mir sister, the agitation was continurd anuther.'141 m1w. then dild. with Ill(), tile Coll, 00
00 Liver se~j' wallord with IIXL drkd with CaCh. the Coll@ (hold. off. and the resihor dmt&

0 visix 2 tonctlowl Illf 135-43 and 14, -7. .. Am& and
::I Meow. ll 5 0 "r I-t fract4mi. stem
yellow platest with okharp oulm, und, wt. is 04 tit
$t
dutnt 4
XXI
11 it
1
h
d
of

00

0 111 ,
.
o
of" a
.
c.. I
,
efy-t
2d frosoction recrymd. from hot ale. gisio
1 .29 X. of C.110 (K - M)l a 02171. lu rr o g,
4-
2
5
1
-P
arr X1 and V
t
d
81
00
00 -
.
.
.
.
. 1.
C
). a
XK, tit. 81-2% which ultrated with IINO~ (
(211111). tn. 12"'. was mtpd In OA g, yield by refitiling I hr. 4111111
A tuixt. of 08g. XXI In 215oct. Cells m0 Slr. PhNIINII, In 25 cv. Colts, then the Iwoduct
toa. woo.1mt] with 30% IICL the Coll. distd. off in m~ and trcmtd. fimmu Clich,
so

pithdaythom. us. 1l6". wasobtabord toy mixing 1 4 a. XX with 1.4 a.
stmt allowing to "Wilts. 11; 1144 4t2-7. Parro-m and
XIII Ill little CIICI&
V

0
.
L.-vir (r. A. 23, 54M) dinnite the strwitures I for momt~r to-k and 00
kc3liesloolde (XXIV) (M.I. c.) and VtI (Xffkboff. C. A. 23. IK-47) I.w It. livil-incinur
CC1 and little AlCls they 91,tainedn. m. M.4*. Ftm the low tit. p. tif It thry
%to
00
0 j 00
so
0 to 000 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 a 0 0 0 0 0 a 0

57 U
V2,

A A I A 1 0 It a U At U 16 v 4 0 11 a 0 a It v is x a I
&--A- a- I # a '2-11-t IL AA-M- M P.A A_v-j- As- %s--A
^-Aa itla fixe- IMP. to
A.- 14- Poem
A i"
00 A vionclude that the "III Simmaii must he to the fo~ eum! Suit 11141, 1. Vsosd1'111 1111NI
I&, 111 1. XXN &"it VII). By the Wism of the mr*111N' a
t Xxv~ AM NIC&CIlt OWY 1, l,3.&C4II4?II*(0mr rNtrv (1XV11), in, ZIA% I
N wwle
.,ib that abUltwd by I riedel-Crafts Weethedit, which proiluced with It, the
aulber tausA m M" and with MCI the At deriv. Be. 91' (&o L Ir.). The strum uskor of
'41411mrs 111114,14 ;lpUlned by the Influmei of 3 N(% grentp In the so-possitimi to the Me
isin, The lindings of D. ated L aft be" disputr4. In the It% lov"Itiestion it WtA
t1st ndIrtly lived thes the leirt-flu group In U it In the ti-padtion to Wit (Krtkha,
4 The 1=411-mi I bluet tuatalum 04112 In ties 111tratismi 11111 Alan 1-ClIhIrv the js~
so 48 of the Wils(Witerr and 8. *A it. obtainvirwith trot HIM
*site AlClisand purilled by=. Are. 23-4"' and not 23.4".
t0 a the work M 1). and L, wpm ewe ully repeated following their lumdequiste data, Ilse
1wqv%x-,-m-crcW used by D. mid L. proved to be as chiltned
I XXVH). this was maverlset! to XXV and then to lAd-Collahle(ONle)LI(MI (XZVltl).
.3 1" M* (Schm I e ) Prout the Allmod. GIZZYin Huoanslb,)~UuCl wasubtalned
XXVI dint., t tma Vm prrpcL to
w .1
3*wb11eXXY1bvsI()"'&ndm.fi (purifledbylliverxiisers). HYMIT.U.-notXXVIwast
09
CUe&XNC4)*(X=). in. III". Immmoruing a vetyraint
60 inink adier. and a manco-altra 4M., tn. 82-39, Witte no mink ochor and diffelent Inson
XM with whk-b It gins f Ats dislertsIken of The m P., Its protalsle structure bring
00 =16) lies
I,3.4.G-C*lIjJste(0MvXf (XXX). Tim forsmatioso of R (VRI) And the anther
taink by the tnethod of 1). and L is not clear. neither Is the isolation by them Its the
pfww of a mona,-nitra compd. "s. 711, which citneld not be obbehirt! in thr pirrim. Ise the
amtm-r mu%k and by nitration of IM The assoms-tim that the mice of the arnbcr inselk
is emiditism" toy 2 NLI~ groups In it-poaltissal to the Mir er"oup is con"ficted by the
140 that the I iqk XM =notes inner Isintly Than the onsilwi, mink XL Eir/a.
-;J4.00"
Is
VIW; 77- 7
&A 1 1614*3 411 Ossil Olt visits Chat (3- Ass
U a AV go At so i ---1- 11 Is I v IS a a 3
I"? Doi *,Bit* mars elegant" $!"A",
0 41 0 0 0 0 0 4111 0 0 0 0 * 0 411 Well 0 41 0 0 9 0 a 4 4 0 0 9 6 0 0
41111 0 9 0 9 6 0 a 0 * 0 411 0 & 0 9 0 o4 0 a 4 a o a 4 0 4 o 0 0 0 0 *
-00
-40
.00
640
soo
4:40 0
400
"90
*0 0
.00
'60

00
I 00

00

4
W)
l I
f
IM
120
f I
4d
i
U
i
f 100
A
on t
~
Us
i so
on-a
ce-co
o
n
g. o
n
e
o
wjt
It
r
S. o
6, o
m
ns
It.
%
0
I(X)"- A
washing with 11
o
d 1 9
ourbi
Into k
w
with Pt
Oll th
t"
tkt
00 c
v
e
.
en p
g,
1
l
g
,
,
wit IMP.M.Wapt. the 960, dists. In sarm antl recrystc. Itom porw4cum rthrr MV,
00 WMobtaill"I In 115 9,)-Icl%l whoi S71 MetFAl.wai
V KOJI
throMof Koff addkd
tvitu":1
XM hiWm o12
4owl
lidded to 124
00 ,
.
g.
.
y
hm in it water bath. t0d. with Rt.0. dried with N&*SO%. the RtIO evapd. and diold, in
-
$0
09 W Tpd. when the 161X rou pd. (frtwu 2W.1 X. of XXV. 2 4 X, of
M1110 1XVIU. U1. I
r
and W ce, of HIM) was %std. 2 5 his. with dry 0 It with kr-
mi 4Avi"ss. a crystal 4 00
confine. Own devocupd, with Ire and 10% 11C]. filleted and rec"*sId. hom air. XXVI,
h
of it,#-DuCl ww. athl.A to th-Ni
)(43.4% obtained in 12 a
ield wlwn 41
7
c~
f
o0
00 .
. r
e
. r
jr.
g
:
of Ine 10s. Mo 10.7 1. (A Mtl and 260 cc. of &be. 1140. the reaction allowed to subsWe
ether
d 10
110
th
i
h l
d 0

00 e
et fin
ecanW. w
t
.
(2hra).tbecredusedlihm a water bath.
%
th
bi
d
d
d
ith C
i
C4
2 to
w
ne
r
e
a
e
ests. tom
.
.
ISFer INVd.. am sq. I&)W C21d. with VIA the
00 Iftio expe1w, Imetionated,7 th" in -'-P. giving M-MecilWhIe. b. 57-W. and
* so
3MV1. which was cooled with im, fihwvd cold, twice fmten out. M. 11'. XXMM.111
. 00
oo obtalzed in 2.8 it. yield when 40 s. HNOs (d. 1.61), and 10 g. 33M in 14 g. ActO -
00 wed separately but at the sum time Into 9 a. of ACkO at -10* with agitation (no blue 00
=19 d the reaction liquid was 0150erved), then poured on let. . filtered off. washetl so
00 with kilo. recryad. Inan ale. Theak. mother liquonfrom XMI were
'
00
of was dimdved In
ennubtsed. loved from a1c.. and distd. at 13 mm,. the fraction ths IM-75
'
.
ak. allowed to stand several da" at -2-100' pptg. 0.1h t. of XM In. n'1 of
o0 CMAIL BLANC
09
00
00 00
00 of

00 00
so
00
so
0 0 0 0 0 0 6 0 0 0 0 0 0 a
0 0 0 0 0 0 0 0 9 0 0 9 0 0 0 0 0
0 0 0 0
0 0 0 & 0 V 0 9 0 0 & 0 0 0 0 0 0 0 0 0
0 4) 0 0 0

u W a 16 is V IT a it a a V a is a IiI A# 41 a 45;C
III V Y I
B&OCtm of as bbWAS iompmed ad Wboso-O-capmet. S. V. HCKWANU 00
so J~ Gra. MO. M R.) 2,770-6(19:12), el. C-4 kall-PreykwWrit I-so
that the hbulfite COMPd. (1) 0 UIUM4-ftaphthol gives with N14011.11CI cot the
00 If d U4-naplitboquinoic diosIme-NaH9D.JU? but IqJ-CisIIA:OX-NOII)- 1-00
=41,M). 1311ilmoututralimtkoolthelICI N1,1011.11CI with AcONa in the
rescUm, .00
v, I then Is obtained CJU:NOHN.H*M (IV). whick heated in &IL mediun am
steam-distd., is couvetirted to Uit anhydride of lAnsphthaquinome dioxime (V). while Ap 0
a CjIr__C.N~O -90,
.00
6XII.&N
it ;; . I
M (VP fee
00
Gia 0 Go*
00 21.
of zoo
00 -4 y see
Wa
ti- 4:0 0
0 1
W01"Wiftill which t% 10 iRt of I with N11,011.110 to #A acki
ZOO
nwdium. intradviced to boiftcomd, HC4 P"Umd 117. which "1y substanti-
11 tit ate, the bypotheiiiis that in the reaction of I with MWILIta. if is the fint 800
intcrowdstriproduck. Prtpa.*fEL-AtnhLofll.Ot4g.linl5OmiftOf3..~Zg.cryst.
AcON& (10% excess) mid 3.05 jr. NH#OH.lia (107q excess) was gently boiled 30 min.
(wbea a ample of Uw red resicumn midst Two4umdwith NOR no zrftn PPL cif nitroso.
-naphthA). then fikered. the 111trate evepd. to 25 cr- filtavd attain. wasbed with 20 m
11.0. cooled with ke. treaft with 6 cc. HCI d. 1.19), Jet Stand 3 bra.. W PPL filtmA
off. wasind with IS cc. told; 1110, dried over 40% pwd.. refluzed I hr. with shaking tie 0
A I a - I L A 111tVALLOGICAL LITEMATURE CtAIJIFICATIOW 94 71-.111 too 0
slow 1111P.11111ky. ........ . %lam, 1114.1"110 Its*
1mkO*) -it -5., cot
iiA t S I IM 0 0 1 1 9 14 9 a
AT K
'0
o, it 0*1 1 r 11W I
4, . 00 *
#0 0.0 * 0 * 0 C 10 lop 0I$ : *0 Cc so 0 0 6 0 0 9 0 4 0

0.
IONH RIP& P411PIN q3jqA JU'S 9Z'q lUffl,41 all 'llp -1 'jqjA- pjM 10411 p
*61" 9z a) PJAPY"W'90 PAWIPM 3p1u3atn.puwj1*jP"olPt;n%njq 3qj '(011 joq w0V
R)!Ak Pqs" 1311un) 4q) u1 "Wo uaLoAq Ipmn 4qj -)oq paMpj %Y11 ltqppe Aq p-jwjupnu
2Ul.Xj pilloqUatll J3jj'P-7UjMAjfpw4S-0QjojUj2upMs
ipj- suqt-d IM- tq pmpoA -4v lip
MM IMSAJ4 IMJD" 'A I WT . 12 OPH stilm amp pas -3p -lip Mill I -ipja Pmmm
0pjHOvM*x)0lpuw&jj
loll v I)-.,Ajb,wojd
%fit I 't-O'M "S PUN 'f)l ('Dd--Pr. t-al '01 O1H-JMM
Paw 'OCR '20 CL P 11itu xnlpoq is UW4 wipm Aorl" ap
tt q1tA01HPP3-J*0Qj1tqpaAPnV
"a '3 I'S U-111AL A w" P3u) IvA 11 -UA OPM31 Wq IMP14A TOfIll"M VON 0-H IPIA
PXP-'P-1Pj,Ol11 - ow u1 fall woe 0101 pAnod "M pnow Alpmsvj.
.2 s q1to Olt
TWo3 InIsfil. p4wul SIX tooltm 1 *33 001 al a a 1 19 to
.UPSV-MAIO*%4jjd -UAP%mk'~HOWXRT01Plv1r,
am
pav,jp qllx WaT P- Olw-m ul OR j* tint* 10j"'.
It
p
.n W-'3 91-9,1 2UIAO "P '33 OD q1PA paqmA pn puglij 41
00
it-i
00
00
00
00
00

fluu IU1% Ull its if JM,- h h- IF X,;!.31 Wilms 11 1? lit"M &I 004tarw
r. - ~Ug%x 111-~
-A' ALLIL Mffij~k F VIP J I f VAII-A
-- Ul
41/11 ~"*fo
4q
A i
00
0:
00
00
Catts 4.1mosidialr4tolutat. $,V-1logdAlintr anti N.
.4~ 1r !IV Mobs-WiJiM F-vs Ats. 104. A artstsiv-i bw .00
variv .1whaw ohitlaili'MI 44 ilithle III Ittri4l. bl, Ittitictit"I III
highn usMa d N' Mo tv thrit isitil. wiib ivelal and "
and diotraputbw it; Milivikin ttri'duct, 44 a mial. W it A41
with unn4ductri oxide. on a curler.
=00
CLASUFICATION
Al -00 It I. j, j j j
it st U X ~'w i i !;;
0 0 0 0 6 4) Ov 0 0 0 0.
0 0 * 0 0 41 0 4 0 00 010
40
00
t-t
JA L I v W a I It 9 a a 0
0 0 0 0 0 6 0 ; 0 & 00 so 6i
0
000 0 0 9 00 0 0 4111411 * 0 0 !,

10 0
00 0 0 010 0 e 0 41
0 11 0 4 1 4 1 a I u Isullu am Iris vii'm 3,p WON& up Mies 41 4)4L) motlo
I-A-L-L-A-A-L-A-L ALMD-Itt %.! 4 k- Q
00
41
0c _;.0 aill
00 i tie" Asiort
!"00
00 sotb"b of i-00
00 6 NW V- A-~ lvwwva. A*ahsAj,,umrAmG)" Prom 4 7 13
(1934).-Tbe rmdti of the elpti, study of ti~ eiis~v .10000
MtthD& Of PfUdWtillM aM diWUWKd. I'WntY-Mle IVI".
Chem. 111atst,
00
00 91
0
a
o:
.00
atlb
=00
roo
glee
00
00 d Nes
OW 00
00
94: t
AS04-SLA 911ALIUKKAIL LITIPAIM CLASIWXATICN
to
U TL AV T
4w " It a It an liazon ills 0; -,
0 or,
gap
o;T,q*l 0

*a 4 1 A I a 9 " It 4 11 14 U IS to 4 WN us hill line #I get v;,C*
A a L U-S.,
r#Ortills AND Peferselas ..I,#$
COM00,04, of ibe It. V. - - -
0 oloqd,-,~ LVA(W-V arm V. V. lkvwA*kihd

0 .
A144011PAMA441M Prove 4 70-410914I.-The sludikfaf
fix, "Mi"Onaphilhas aWI licir dMvt. wu becull let
I
h
09 Off, Productifl,4 af hydmxyrittrom m Is
l\;
F0
tg*ttb&. cJ,t
and a-C
11
014
2
& a
1~
P
2 NOdcriV,.Of".C,.IlMlI VnlrrrtlXl. fly 101MV011 nWtbWt-
d

00
10
,
,
l
,
,7
41(011)11
1
2.4.. 2.5, 2.1t. and 2
,I
7.II()CJIj"I
n
2
2IV4; U. S. .4. R. pill. 21,M) 4h,"re
H. (C. A
ill
4)
%C
IIA)II
2
1
"71

.
.
,
,
., 2,,?17.
and 2.3.7-11WO1,190011'. 1.2-. 1.4. aw I
s-11tw -
w
$ sq-
.
t,
that life
6
.
.
1jel Kim h"Clu wilwil
Nilitill
~0411
'
u,
WHOM. Skill 1,*4,11.. II.X $",I .
mn by Mpl. five dulk-ulliv L4-taillif 1.2-4
.00
welt Preful. Irs, the ftaunw~ tivirthevil cd acidifying with
IICI a sailts. tit musixmakles of a cunsfid
%'
nsived wi
h N I-Ifill -4
th %'IIA)II
i I w .00
.
t
a
%.
The tantestivin of red
'A
4v
1 b -firinhwIs with it. i
juv
lw
f-P I'
i 00

aphtlublau"Aluic "6 na Der
i .
ud K p
3D
IM71 ,be
llIll VVIAICS111V it I-AUW-1 I'T thC
irac 5

3Z: .
.
is avuldeld by carTyinit tas the rgiatill"I lot i-A* and Willi- the 14141l, til-Rip
Nil Ollull Olhl 'he .00
1
000 ii dtarw loci bri4a, the suffit".61 t!-Aald. O-Naphthil-
1 dtilibUtliC And n-OA
11411061
11
1 as all khli snouls sit l".ilk"i 4.
l 00

0 3 4
,141
P
C KiVe uo CAAayd
by-products &fill call be acklifled at &41
1 s
acids with NI-1,011 give 11110 0`11Y thv d-nitrima c,"Ittil
iltall 17-11"Is
i
icsudicss til thr ill
1
,bnI d
vi

00 .
If-SOJI arts sluesklily. triouking a Itfuls. of A-10. and 41
".jjaO
,,
v
.
s
fit oil mud Pilot groups in the ring- I'hwk 1.2.4-11-Wo- j . 00
,
If#-:JD% VICOOM Of N4140r. The nitroactussilitlailstitfunic
I acids uxualty finrus ilablv, ft
hi -
lt.(Oll)80.H and gave 1.2.4
*
' i '! I.
00

. w
eh cu
n he nvrvsttl.
Invil hot 1110. oul, 1.2-0W
11
011 W
1,11. 1,
ll0C,JYNO)N
ltk Nil gave
8.1lOCvl1s(NIl
2

9

-M.-
.61 10
8
111110V -f-CiJW11 Kim 1.2- .4nd IA-110C,J1.011. ti~
arpt. of whk1h to havA off the diff
A
M ,
.
Wh
AuslivouslY
i

k avis v
u
ilirsuf their
bkulfile compils. (cf. %'-washimm wilit It
C
A Kall'r, M111).1 102.047*
"
. W
;qjo .
..
. 23.
2434. U. S. S. R. Pat. 14AVI). I'lit, hilk, nm
it
31
4 and Its
1
'kNlI 41~
1l
iNll
le 1
2
4 C
Wh
khIl
_ -
m
.
IlMoliJkloll. obtained Will I
!L4-CtNC
II
(OII)_ .
i
.,
,
.
.
.
o
1l
tirm-t *till N11
011
lAh C
tNl 1,00

j, ,
w
s
*X%H by "tK,tkm With $jit,.INa)* tior (cf. hlar-
'
h
lk C ,-
-
#
.
I
.0 an'l
i00

! ie
C
. A. at. U10). fiftAlw"I a flow No etv"Itli. with
a highly n2obile S(V1 group
in whielt it retri
bi
1
2 ifhot. with :1 --k. of N11.011 I cbes
Diane
,k)
NO
Nit 1,00
t -
,
n
vs
.
fit huquinmir-4-sultanic mitt
I
i .
i.
,v
)
I

.
t
rrs Willi sq.
1=1111, at "hl"t 1 1
0-44:
2
4
f 00
~
,
,
110
ollmilla &led
its 1, 11.4
.1111h witle A% 1.
M 00

R A all
. too

, %304-

0
1
sollis

,
A
U 1
U s AT il a It a af A i a W 0 a
In
,
6
0
0
klizr4 ;4 A,
E 4

0 0 0 a
-A-
go C
00 Is
00 a
00 13
#-W-"
9 to It IS
TM sted" of It &wwk=js% as Ceftaist saphtweas
1. 1. Ltvkm,. J. C.,..
CAM d. C. A. 27,
2M~ udxl- Of 644 111traffio-fi-naphtital biWfitt
-pd. and 4.8 g. 1.2.4-aminonsphtholmilank acid (U)
alow%oadded to 3 C. NH&0lj.RCl and I cc. coned.
in I
11CJ in I (v, W11118 11,0. The W Inc wu catitinurd
for 10 0"0' on 0004`481 10" 9- Of N114 2,I.4-nItrm,-
naphtbalmWonate (M crystd. SmIlar irpstmem of
-am
11 witb !Xv 97, TM VAIb 2 14 inansphlbol.
Swank of 11, the ykM was approx. the
whe- NO reaction Occurred betIrm 1.2.4-naphthalene.
dianthiesuffortic wW and 1; witile the 1.2A4wmer lamed
an unknown ultraw compd.. and the I o.5.10,aner lamed
2.1A-M-080 btfialwilwate. B. soyenkoff
Ass-ILA &IIALLUISCAL L"INA111611 CLASIVIC411"
. ..... .
.00
000
-800
so
06
'09
690
'06
goo
u 11; AV #A I I I ad 0 N v I v a
o to
a 0 o * * 0 a 0 0 0 0 0 0 0 0

tPI)COMO A
J. 1.
0 goo
Zoo
-A.A-
I'M AMM-t., ~11
000 . . . . . .
eg, -3 -1! no*
so. Oll,
46 di.
;fl goo
jog 0
Amd
p goo
no
zoo
use
-A I a. S L A MITALIMICAL UTINATWI CLAWICATIM me*
Iris 0
946040 Nit akv 4349 1#"&" M11,111 4w O-W m
0 An A 1 V ad 0 0 9 1 ir so 0 a Irl Is T
u AV go UI;
@1* 0 of 0 0 00 0 a 000 0 0 goo* 0 0
.2 2r;. I
Wo * so 00, 6 0 0 0 1& 0

w v III
1 1 4 1 6 t 1 0 16 It I 111im U13 is]$ by Spa 41 4141 Marv
Is US x 11
g A
..No Oscrist-11% 1-98.
"W. S. V. IU*dawv. Run. :.so
Is* ~*ZMK July 31. 19M. P-NaPb0VcAl%-tTft(edQt9tCmP. I
Twil in an sq. of 0k* medkm with IFUlfites in the
ram of bavy CIA? '0k'&" fat t"Mrk CuQ ot Mit(h. -00
00 It'i
so
00
coo
0 A,
0 ice
!see
use
Its*
too
tie 0
slow 1111~9119.
0.1
41 34 a.. .11
U a AV, 10 is is I of it 3 s
:0 to to to 0 4 aAx9 1 Its
.1 U U
0 0 a 0 0 0 0 O:e 0 0 0 S 0 0 0 0 0 ei
00410010 IS 41 0 0 9 0 000 000 **of * is 0 0 0 *00 0 9 0 (P Is * 01

I I I Ij
SO: -3
too
004
:00
00 gl :i
MddM. S. V. Bogdar-.
jd. (U Ft. ;tj 1, 678-M 39M)
pwtke of the mWomflOn Of afmn*t'c
the tbeo Cho. BLUV
"dnpd*"w" tiboot TO refffeOms-
I a - 6 L A4lTAtLWGK&L Lllt*Ali*f CLAUVICATION
L
l , _- - -- " :: -
g li-w -11'
POISVO . . - -1 1 - .
0 of 0 a a one
It A.-Al- A-
I-D
00
so
-to
see
goo
roe
goo,
;:so
Nee
.2 * 0
t1o 0
are 0
1
------ --- - MJAI Ow Q-V All
Ir to )j 1"'ll --I- A I a f" a I v so 5 a 4 -W
III -TD 1". a. .4 T .1 r IN K U It LID Ral
0 0 0 0 0 0 0,0 - 0 : 0
0 0 0 0 0 0 0 0 0 0!
0 0 sees * so,* *a- 04 0 9 0 000 e 0 0 0 Is 0 0 0 0 (1 0 0 0 a it,

11F~o so too 0
0;1 ~ I) 1 4 1 6 1 1 1 0 11 U 1) 11 "'1 -T-"
I L - A-4-A.-A-JL-A-A --L I I., t- t- 11-1-1 -1- AA
SOWN"Oft *ilk *'all& of sullwous Suil. I T)w Hila
i-00
Matti" yovisq) S. A. Nbs J. 6-f-
11 ~-Xl# It IM1107).- Aometslw MI,
tIrnfilwa, with Wilid" we OW110VAI 10) (1) ant)
so C ;~ I .-to
aminustillonle ackh 111). the relative Anilt. oil Mit, h, mr-
t1adjus to Well simi Moser it'. A, 16. N171j). remain .90
00 4 cisn%l, for an Todri. the vo6lity.4 this. -00
It. and Uh. Wimly the i"hu-tion A I'Mit IIIII anti of p.
4,: WC41"01 RV) with N&IISAN (V). undri tiuk,) ripil. -00
41 ctnditions. The use of orutral V 4exactly neutialised
with NaOll) Irtatils the mtc of "actitm. V, cot,ta. -00
411 excm NAOII M With W, results in even sluwvt trac. 000
0 tioss, which withV is w2letely stoliptil, In adda., =00
neutral and ilk. V with jPvt 'd' oducts.
1000 Neutirtil V with M gives considerable PINSaft (VI) to 0
lopp-d to Wed, Ger. pat. 151,134) and with IV givrs
age
not only P.MtCJi.NHI, but also P-%IcQi"HS()sI1
j rGo
(VU) (oppowd to Walter. Ger. pat. 109AW6. V, neu-
go a tralixed 23%. with M gives 87% VI and with IV 73.7% ago
VU. The ratio of I to 11 is indepectilent of the it"tion
00 2 firne (1-10 his.). practically independent of the coam.,
but 6 not const. for any one nitm compd., the unt. of U
increasing steadily with increased alky. The maction is
rstulated to proceed with the intermediate formation of is**
0 &W NIIOII oompils.. unstable under the exptl. candi- I zoo
%6~w uwd. Twtl%-e Wrivocts, John Livak
!see
=00
I a I L A OFTALLU"941. LITERATIONE CLAISIFICATION
If 1W
41 A too
taftbas 44
U a AV so AA a Cw a 0 1 a 0 9 a
4 Or 11 g a It I I I U., 'A I
00 00 001,41; 60 0 Soo 000000 0
0 41 0 0 0 0 0 0 0 0 0 0 0 0 * 0 0 0 0
: :1 o so 0 0 4 000 0 41~,-

al I . I
I
K --
I
LULJL.L.L
, .

00
IL
R. T.
At

well

A OU&LLIMC" UMAT%" CL
to" so-AmI
411
Cos
00
0
Colo
No 0
Inummal --------- I
low
ts
.0 00 0 1*4 r
0. 0 41 0 00.1,19 0 010 00000 0000 90000 0-000
0 0 OLO.O. 9 0 -0 f _0 0. 0 .0 00 0 0 * 041000 *see

Ox 1 4 1 6
it. P- A
00 A

00 C 111amdom WO Mft of vd1wous add. 11. Simul-
was" extilmlea of 0-motlaol and *"live Sullite. S.
00 g Va goodu o wW V - A. lvamvit. J. (;#a. Chem. W. S.

to 0 a T;
R-)-V. 204413(in Ifuglith MUMIM71: cf. C. .4. 31.
-577".-Oxidation Of a will. (If a."Johliall (1) alk) N't,

00 & -4 C110 in an autgWinve at 11%1-
Sch (11) in No by mean% t

00 8 Avid
fwltlMim fit 2-1141,111MA
l
t
0
00 j A
l.blit.
481) And 1110111019 Ill
list, viehlol Ill.
"'ell
4
alut It"
l
'
"
uc
"
St the CZP* Of the 01111"tim lvm
n, otubovItlittlecirmtoo ywd nf Ill. Sul"litulioll
"XW

of MOO, fo Its In vownpletv
r CUO in a neutral MiAlm, rOu
00 a
door to I "to Ifi. In & MUIrg Mr(linnt CuO vhanr~
1
00
0-nSphlb(II hihni. but alkali retard% this It-w-
Into P-WftsP

At
don CUO (of Muth
130' 01IM40011 01 Nllq% Willi
00 .
W, to tb g foruMtIM of NaOSO,. (Ittildation 4 Na,"A h
00
, with ,k at low tenip. Is retarded IlY lbe Pttllttlee Of L
The f0malkm j JU can be trtwewnted as a traction be-

0
v
~ and a product of oltidation ill 1.

wl
p0 A I
all s liTiii-lo-
41 .1 U ;,'e
0
00
-0
I ., .00
0
so*
ell-S.1 41*1 -
a,al agot IM 9 AID Q
to 0a 0 9 0 a 0 0 0 0 a 0 0 0 0 0 0 0 0 *1* 9 0 111 0 0 0 0 0 0 0 0 &
0 0 a
lie

t of i
1. 1 A I
rA re
kJOHL-
PROC91"t AND FOCOO $Ms WMA -09

00 U
Tu
k
k *00

00 .
ev
yu
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it;;. 5,
= Lke. 31. 193i. 56%Z;j

0 0
tMk
adds an Mtucvd with doc dug mod Bel
t
bkh S
C 1*6

8
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A
o Us been added.
4
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0
to

*04

too
too
too,
Atil-SLA MIALLIMMAL now
Kom 11"llsvp RUN
104666 on, ON, A* INAL&I'l OK mv sit
v I Me a a a a 2 a v

eLnl,
IN

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owl .
04)
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0*8
0 OR
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J
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0-3
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If .#-A -Iloil"
i1q,
06 $146 a-*
1
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two
INIP or
tNaNNU of 40
n' fto "rl
t
A144LA AVALttfttat L1116ATON tLASWCAVIN
00006001111 61-100-044
a Is so A"
k%ft., UL ~bni&
No-,
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MW Sqj NA^
Wk 'I . . 0
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MLI IQ$ 0!
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6

ow, 0WOW to famma"

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R.T. Nos)

use
us*

9 1- 61

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.
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I
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iW1,

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Poofill mots

log

we 0

d pqmqpktbob. of
(J. ow. Chem.
47 41t
06 CC
p. i4
WWI Oak
coo

Ogg

coo

low
INN 6"Anw
tobaso .10 dow a" slaAal WE a.. Lt,
I it w 6 bo 6 0 a it as 9 dl 0
I,, U 8 AV ml; of 0 Al a of
0 09 0 4k 6 0 q 0 0.1 0 0 04-.0 0 0 0 0 0 0 0 il 40 0 0 0 0 0 0 0 0
0 f 0004 0 tie 0 0 0 0 0 9 0

0 9:00 HOORTORS OWN

ban*

NPNW*TAI (J. 006 MOM

go,'. -00

I
goo

too
2:7.
and -d
to 76-79
Tmso X 04: gal. see
~
R. T.
phank
of*

so*

MAMPIC
&a SLA O"AUMMUMMOIN ATION so#:
Stan S?"* A" Igo. law
1 14&# elf 004 4"t 88AA31 Ga Q.. all
a go it b80 is 4 1 WW 9 a 9 3 9 1
0
0 0 0 0 0 00 0 0 0 0 0 a 0*see 0 900
.
M--6-
2a.
~In "Mi

T I -- T
a -cap! ;ills mats

few
0 Ai (;!;;t dy-
5 %e uAt

ee
dye.
--led by WNW Of Zu d
Ust
i

ut
vated wi
th C. in
Nacl own,
see

oft moo
00
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ego see
eow goo
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boo

&A w. Ask
10,110 Ole 4WIF 084 - (Id 0 0 9
1-
l
-
r
o
0 0 0 We
i
_
-
00 0
goo -

03 ' I *too if 1111104114"US? Of a a a a a a a $1 it a At a Al X? a MP 4 Al a
a FA-R-k- I - k---A- k -1 . A
41: I&O.A.0 4TO 01-LILI -00
PEDC911ti AND 00"161-11 0*011
Dedvatives of Ottic add as CAPMN7-active substances.
A $1. Kawkin juid S.X-Baidamaw- (hg. C". tmd~ .041
(U. S. S. R.) 7. 108-90940).-Following the getkeW
patent provedurn 110(CHOP&M, HoN(CHOOMI (tau. .00
rine) and WIINWHO"l (wribyltaunue) werv r.-rpd. -00
AKv1c=%&vwd wilb Wrx, *,id t. P.., tg~~ A And is".-
iAubWtks W the Lktrttmts in watrto ild. -00
S. Mats AM alvAl" &TV lahastm.
410 d
0041
Goo
goo
00 a woe
Goo
see
woo
vo*
to
lit
a It a of FALWAGIC&I. L1191altof CLAULMADON
woe
%via** -40 Ok. Got 5A G-V 11~
340
a Aft I I 1 04 Q '1 9 it 9 All 0 1
U 9 Alp v
gt
16 o
0 0 0
~44 0 0 10 too so 0 0 ov 0 0 0 0 0 000 0-6 0 0 a 06 so 0 0 ID 0 0 0 0 0 0 0 0
Im., W-0 MIT.

set
000
* 4p
0 dial
sell,
s0-
00-
04-
VIM A a
Afto slog
Not
13 31011111HII IV31WIl III
Aq
a
A**

I
SO*
1 00
11, lot M SINWIN
.
to
44 goo

300

slow S111614044 dmw totti"94 ...
..
..
--r-, --W-. -TTT
i* 0
t9 It
Fell It 0
-

!-00
-00
sovemilm With "Ibi at suallf"S acK. TI. OIL144- 00
w4fital with 1"Malue: Nitro COMPOW"s S vatiald" Of Dull"Imlilia Actil"I. III he tiserworee'lit wlfo. -0o
ie" of J. Gen. Chew, (17, 4. ti. It.) 5, 444 Ou'll"S 110 11'"llkill-i tile revetioll, If llill" rwnlkl%. Will, sell. -00
610 ill WOMI ill its rate. Afelturnilly, mullarlic at-his
'Oil I
MA &SIM vninvillsly), V1. C' J. J4, 406M~-A o 0
off not all Wirt will lilt I. Ill tile (4,11114titill III
00 97.4 S. O."Ittittleturtle. 211.1111 X. 11-haphthol still Z11. V11. Action of OMAN on I-dialonsplithalsof4- :10 0
XVA S. 46.2% Na.9th InCANItV. viutvr wassiltrett Itir 19 111119111411 410141- 8. V. liewt-twil Glut M. A. SwittvAll,
bm at 1106
goO lalle'. filteri-d unit tile bittate seck"fied ley IICI. Aw. lew-W.-It let phown that ller diastl grovels 44 1.
dioutoreaphellialmse-4-oullopic acitl t-an be cholux"I into
094 sitar which Me mertid. M&Phthtel Was amid. with beentme. Cleo
ervemisne. of the sq. sabs. 1-.avr a rnixt. of sulfate musef Na malls the hydroslat grout) by NaepS0.. wills omicurrent. fortuation
sew of 3-ofte 1 -1 ollit., Sir and ile-tt urnew a for . of a "Phthylls ine-41-leAtIftenic "I and the 2,4.di-
. In SkI716to VIVIVIS. it less shtivill 1114t with iact*motde- we V110"dial" rin,ifell. Ifirin 15.11 x.
I C011*40ell Wall walliml with soll-t tit tielitrulily tliul out.
vivitindi"t ion of lilt Nat NX. lilt Virlit III VAPhUkll- liflkled In Walter. allO ithidl it .. Ill-sle,.1 *ilk an Alk.
M unit- lww o6 ill" thir tolul Vidd of lunillel issfis. of M&.4(h (tt,wit the a. 36.41', '206
frons the nitrotillurze. OR-MCall.&MI, as tiw No all
A"
wm d1sool"d N4119% b
(0.03 M). and 41.0 M 3.3-110CIolUSAMI &!24.1A X. 44'j, NaOli. followed by 45 No.
M.251
d builed few 0.11 hr, Woo), at IlClandu-;~Iaf as*
at 106 hit oq. N&Oll VI I hr.: col cotelioll, thrip Ima, owlSitiz. I'lit. 44 it I. ltlis(o life
merid lit list No AVIVIr dokt Still the SCW Yet DWI
y (on plarting ruselve-hil). It U thus aboleirm dot 1 0 WOO
I, koducts Of tfouiefutillatim W Pullumis wwo- livir"I o. Ill MINI h
in. Rod tivaluirlit Willi lit'l. war" 0 0
durinS the reaction of NavAh with nitro contreils., M ex INA
I L At StIALLW"ht LIVIIIIIIIIIIIHII CLAIMPKATON age
Igo. Or
see.- **!!t!!!
cov 409 ON QN. 41%
r T_r'_1 All I to two ltilitkent 2
U IF 9-. 17'r
w IT or 11 UP 01 r,-,, ~,,U! Of a I alk em"
0 0 0 0 0 0 a 0 0 0 0 a 0 0 0 0 a 0 0 0 a a 0 0 to III ol 0 0 41 a 0 a a a 0
1~!. 9!. 1 00

OOA
**A Val. AW.4 W. *0
Y", ~ (;- - t '* is
'R.. ("U &" '%R
-09
;~I. C. A. 99. ratool.). 1.2 mob.
ijN&1130s Sabi.# 02 Md. NSOI1 and MO ce. water wexe. -010
liodul for & bm the ~Z conW. and cooW to ykW Na
4 1jak of m-bi amid . Ice cooling sepd. the Witate, 449
the fibrese fardw evapd. to ykm mom of the quu- alt
'asuic dariv th AfterWe renxvvWs of the sulfate.
Tba Anal ;WAd at NA adt of m-Colybulfaink " Is 30 S..
hm3s sead1w shM bfttod with ridn" &ckts rectuffate .0
ni-t0tiddiDe- TIN firal AlUate CuMcd. to 1(k) cc. and
tivated wM V1 on di-Nd SGA of P-sulfo-M401YI.
ildlam* ="Whar, so ilp
witb ttes, saccedbigly PA. In water - the
latter Cl 7;"
C
00 a A* 0
~add, rKun#Wu platm vvy dAcWdy sol. In water; X4
'34b, thin proutii, F"Wily =1. in water, which treated With
Br water readify yields tribnwom-toluidine, in. 100-11.
hf,
felt
a*
to 0
-Ts-,
nn M Osseo
U S AV to V to 00

I
A
00
0 0
0043
00-
t
00 a
--- 4r~
A- M a* "t~s~6" # _,#_* " - J-,&-
PC" 140 4 4.0 flivolself$
Sullonatim by sells of aulturatims add. X. Oxidatim
of biftilite by ferric litide, lead dloidile, Smd mmuric St, tkiffulmlitso Ill ths, js;-,Jj,v.4 I Iro i~ CASI-41 by
adde. flogdAvlov. J. Grx. CACMI. (U.S.S.R.) 16, the formation tit intermediate Ifit-mits. Aulfilv~, the de-
cf. C-A - 40. 045M.-Oxida-, empn. of vvhkh fruits its sulfutue arids- or bulfites. An
tion cif Palk% c( ffWl, fly oxidell of IFC, fig. Aud flit In the Jullmuml lut-th'.1 WAA for lite Instill. 4.1 Na Ifg
lWrWPA'V Of al-tivv fit) vtutkW-1eAd- to the formation of lkllfiW. 0.1 111144-fit'Sh fIK0V1A~%USjk-1kIt1I Ali 1-704%-- WAtet.
sutfunic acids, the sufftsitAthig mUtiO' tit Or t4suldtv bring treated with O.W. stkle '141's NAOII, 1.4hattA hIr (V'.1 mak
1,111 lif 1,A) (v. ital. r 111, mth?. WA,
dod. by the nature of this, oxidsxi,m A buillas i X N.11:-!Ah: Jltr im
"n. of O.r* nwk Nal 2-hy&ozY4j-nAphthOake (1) and Wkd and fillmil Ism. to rkid, Its. c-Amr. -N, r.
024 wook X&IISOV, IsruiralizeJ with NaOll to the Btabit- Ilroducl, III(SOON01-1120. which Ivraks domkil,
""IS of 1/# of siv-4i6l.)r 11, in Ila) vc- vriLter treated with on hiratin; Willi water, to YkId Itit. sulluessul Qviil, and
1. 1 nmk Irv%% N. i of I). and "led I hr. gave 7.61 g. of the sulfate, Addis. tit 10.7 x. tsf the atAwt ~lt to 0.05 uvole 2-
starting macri.41, 11.11:21 It. more 141111t t--fed by littO twill, OA113 InAr N4tcth, mut WIA
tit". of tile ItVWWA-sl A'A colied. mother Mums &till 0.17 t*C. Watel 1,1 1011% by lummi; its th-- Is Is. 45 tuin.,
a. 12-simphth.1; ~v,~jm. A the tuother liquor 687, ling Ill ?W 41111 sti I.T- a. X.LiCt I, tild g.
(0-m 11 culd fil. m'. lwt bit it jV.j1jjIV 1-1.61LA .%I U M'
arid (111 and acid (911). ul IA11-IY
Itilkle) 41114111-:1 mill, " N Nallm), twoursdiml by Nskoll to jlj,,4, avid s,j wt. "birt, vi,iy b~ its it di-x's
AvAit.1 'I"st, hom dw u1mm-Na 111.
-ls, It. is. Ill's `v. 1441.1. lit,16111 at 110' with PAII, %tit
23.9 a. FtKh aml 1"1,-d 40 jims. wills wiffinx. vvr 2.87 flit *%.
I d .. 1 it
a. startisix niaterW. traccle of 2-naphil:4, 3.69 X. 11, &old IftilhLIX)
0.49 St. 111; whrn the above rractice Was repeated with 511(:". KA%v IIA K. luirly
6.11K mok lw" ')-I inctle %ANh. anfl O-N utole Na 2- urt, which i* appaTently
Nks-W. thels~ WA. aLtAiucil 42.5% 2.- fur sc.%mml d4v- Allhourli thin prMuct I, %Wl CA11allie
'wist. kelwitlival tit flit! futalvar of tile jilml%v '111f,"Imi-I 1,.u 6-1 u-Irt '4"Ailm"Is sunilAr
exist.. u.ilix "d Ifilt(s. Willi a 2-fir. holling 301fild, Itillithr u,'"I Is* tile 11K .411, tile V10.1"Ill, Irly IN%*.
gave 44.7% inisiml suffostic swids: 4.tt% g. It must 4,Qjb M. RM9114fluff
/4:9
A I ft. It A NATALLUNGKAL UtCQAIVRf (:LASSWKATIOls
OJI
$vice* "40 O.V cat dlitalast,
-r "Lill ow a.. It
IS 0 Alt 10 It is 0 1A jA I
0 of Its to It Als dif It Iff it K, on (I( Ila, A ft I A flit 0 10 rV ka v
0 0 0 0 e 4 0 0 0 0 a
", t, * 0
1.
1 00
-041
3well
:lefil
GO 4)
zoo
zoo
2
ago
StIllif)
ago
U4111111

7
a 0 0 0 0 0
0 C
to
0 -1044 0
v 0 0 0 9 0 9 0 0 0 6
`
$ *
.
:0
I or 1 'A tl~ it I) to at v A )i ]a it 121) MIS aspas a a #2 it
'I I I ALA
l
A
ft
A
& Ai *% ~c *
A
-
iti
o 2,n
-I-u
ot
ph1t
10 mob of 4" -'A'slom, Tvilittilim of the St%Wf prinva, using S'A tv. 43%
* -
.
ft
A- am". JL
X NOW NMI a 11-hr. iteatint"t with No. javv O'XJ 0. W a
00 004 N. N. KW"d&dK%* 91vasonk Clievii- sulst. of unrt"itil acid NMI 2-osphilial after ocutifimilon:
;.100

60
.), 1. G90. -R-) 37, BI-% OW all. soln. save 0.,% S. Unleaded ac4d anti 0.81 g, 2-
-
(Iw?)(In Ilumahm) ' d C A 41 633*
pb"41
1 -
-
.
4 call be
nalthtlitil, while the analysis lit the sq, milln. sliewed that
milfonated by X~~-2"No' ic"W444 pikichit, A04.0.0 , hydt"Plaphthoic ada had been transformed Into -00
.00
143, =011117)). HON(Whxh' and HSN& VAGIC. Am givid mild OW1 W. Into 2-
a ramodalm 4d 23 cc, Milo lit 11110 te. 11.0 wit It a ft* drops naphthol. I -oulfoide acid. PhNl(j((AJvv.).I(X1cc.lfj0,
0

.01 PhOlWAthaWn and 7 9- KjS%-2NO WaS bealad to and 63J S. IION(SOX), wells t"Ied - ill -
1 40 Wit WI Mir
W and peated alternately with somall portions c#= dog; after addri. of KOII and exist. with Calls. the sq.
1
0

!avad XsM-RNO 0
mal: 40 s. and 22 it., r
Z.)l K W" layer vm treated with AvOll lit a slightly alit. reaction
l
t
t
b
h
M
U
o"Wd
. t
t
e
s
s. tbeet
opp
t. was uW. #a4 list aid filtered,. m1m. pvv I he Obiwe tim 11%41 I'll NI t-S(hK.
00 4 aft" "in
it the MKII
with C
ll
d
-
.
,
s. was Nvoli
a
. apairsim 14 The all, moln. by firdittly-1- it asto voliquot
0 a %1 -0 drift"Ai esift. Kith &it Ictoll govil K pbellylaillammile showed that 4.03 a. PhNila was huffollated. I%Nli,
C
t"NSK
ti
l
6i
k
nt
o
) as ci
ems, watts-so.
a
ets. sisitilarly, 50 cv.). ICK) cc. 11*0. 100 1. KOAr, and 53A C. IION-
100 t. PbNlli and IW s. HoO ort . treated With 8 g. =K)j orm Mint a form. with mirving. slier Mo. wish
WI
IINO
K
i
d
f
l
i
l
h
ant
P.
a
roll o
ieun
it
A
o
olitin And 1114did IIvO *"it Colo. With IWORNIC, A 1-Ut Oil like llq~ 116111. Was
p
p
'
will
l
bolli
ti
i
rr
a
is
n#
p h3m"yml wit% IICI and pvv 11A 4j. Vh%
Ils. the all.
lied with 0.6 N 110. and tho omi'At.. irvolisil to AS" layer atimick-1 Imia, but the moila, 10411.1 to sivir a test
and treated with 6 s. Koi0t.11NO. itis proeviam of bolling fur a dimmilmn tmijkl. PhNils (*.'.% 4v.), Ilk) iv. 11A).
was "lletted until a total OF
with
K
SOONO had
nd 21
11
id
d 2
8 h
3
NOS(N
I
t
O
i
.
m
e
.
m
m
s
a
.
woe
rr
It.
l
9
ng;
b
d
3h J
Af
id
)
een tm
an.
.
ter wat
nit up as 4baire The after wpm. from Its, the aditt. wu made alk, by Noolf
(
gb*-W"
Of
4
t
h C
l i

am 1
tvapd. to give a No
Is. .i
4mot aid. wit
a
!& 0m *SO. I
6

Portion with 11
I
. 1.82 s b WU ectinvenvid by No waler-mol. cliiml~ao F4&trs
b
Into III, Salto dledr
setiti-v
of th
Re
Ilas
d
l
l
I
1
.
t
i
e pfvn
vn at
n. a,( FlOll to the mied.
1.0). ta
l
AN. Nol,2
WaS
govir 1.02 5 PhNits lit Ill. fulliinaled Ptism. S-Ilyd"ll- mother liquor gavv a l4tt. 0 No sulfale anti sultitt, slier
3-mlihilloic 110641 I'lited to ~ with KoS(hJNO at SD- %be mmovsl of which further evatt"
-4 inars.
Save a mixt
.
.
kif W'. When 0.05 10W. No salto and very wit. mallorimmitin "hwit U PhNllp: shic*
cv. (04 tool.) Nag", and 25.3 ce. 43% Noolf In the mist. cml-l " tv w&kl. it was t%,IW with )III and
plu vc. 1110 smile boiled in a It maim. vall! the 8k was dip. om irmilin
iv vanilln"idlortic ovid an walvr4m* lit,
g p
to
sk-n a slow ruit
tgaml
nt of NO was
t l
in
12 h
.
e
pam."
it
t
e I t4 I No ult fornis utter 4.4, tlantm6c
his.. them vast, t440tivit HA* it. unsixided arid, Ito itoccure wam mifirtned by
the Analysis of the ;*. sioln. Showed that 0.1 g. of 11sis ~dkmmm tattoo anti conversion to v-C1C4It.SOwNII.. am.
brid had been Im Utitwl into I~V4104-b
Kama
o,
dr
G
M
"
& 1874' (f
h
Olll
.
.
rom
t
.
y
P
m
k

tor-MANOVY S. V.
Z7609
BOGDA'OV, S. V. I MIGACHEVA, 1. B. Nekotoryye Proi2voaWye 2-1,'aftol-4-Sullfokis-
loty. J-urnal Obshey Iffiimii, 1949, Vyp. 8. s. 1490-92.
SO: Letopis' Zhurnallnykh Stateyy Vol. 37, 1949

414"
9
i
i.
vo
Z;
~41
�1

BOGDANOVS S. V.
"Derivatives of 2-Naphthol-4-Bulphonic acids" S. V. Bogdanov and I, B, Migachmo
Zhvx. Obshcb. Khim., USSR, 1949, 19, 1490-1492. (U.S. Transl. 1493-1495).
Reduction of 1-diazonaphth-2-ol-4-sulphonic acid with SnC12 in NaOH yields
2 Z 4-OHeCl6H6,80 Na (I) (83%)~ as dihydrate and monchydrate in very sol. cryst.
foi-ms. NaN08 and aq. HC1 kt th I produce 1-nitrosonaphth-2-ol-4-sulphonie acid
alt, ClOHhOgWSN& (Ilfs Action of NaOH solation on III givea 1 : 2 : 4-410-ClOH5
fol, VH2Ph and p-toluidine with II give, in aq. solution,, I-nitr8513-
4-1niUnm--P.-ml.pbO. 3218 degrees, and i-rdtroso-4-p-toluidino-naphtli-2-ol, m.p. 197
respectively.
Ivarovo, Chem. Tech. Inst.

Doe Chem Sci
B0GDWOVj-S- V-
--Dissertation:. LInvestigation In the Field of Oxidizing Sulfonation." 27A/50
inst of Organic Chemistry, Acad Sci USSR
So Vecberyaya Mo
suin 71

r.4
Suffmatitin by valls of sulfumas acid. XIV. Scheme
"exidative" "Umation. Ih 14,111V "I'll 1. It.
Alicarlirva (1vollor Chet". /I...
tilishelwi Xhim. 1j. 136ru. Client.) 20. U-14-MOW-11; vL
C.A. 42. 118a; 44, Mr-AT011S a P:X. Mf U%khoing-
agents. including ioitine, Ifith. K pcrsu ate. AgNkh,
FeCls. and CuSLA, used isi con*nrt"j with sulfit", only
Ivermatip"Ate and 1.0--naphihoquioitiiir4.iuttfcmic arid
acilitdtr fortualit"I of sullintir. acills ITU11% dt-fivi, .4 2
lat to 11twry %tillooAtioti by defiVs. 4 S()t. 010 Ole
tramdwmation Of "Alt W01 to either SO, of ",L). pttd%d,lv
proLveds, Via Complexes with metal kms: metal kins C;-
of taking up 2 rlectsons, sitnultanrouly or tlu~-
up only I eiertiou &rp. the oxhlAnts Win ;.1 elaws.
th. 11n,44(ur M-oullonle m*l with Xt,9% Awl
KM110, (drikkat and.) savv ton u%idsa,l
t.ulfitv) 110 sutfouates; the resulti with 7~utftxne shvist tv
a."isuvQnic " were A-H, . Stdfite with Wine and
II,('h at 50' In tbe pr"ence of 2.7-II0CisIIe,%II. or with
1~-t%vdjaje lit OU-M* in the twmmv t4 2-tL4I,htluJ-4(rw
J-4U110"k. 11616 JIUM VM kS4 In M%tfM%t6~'A% t'"'jWtL
1-he use tit ASA% IM to almott cutupittv t.,Inrtioi~ A its,.
AS &Ali awl almost ao sullonation. while As,%) rave fill",
sullonAtion* Fect, gare =--39~j sullowillon %bile CUSA)4
rm%v 24-W~. (". M. KO-4-hpoff

Sullonatioa of )-aafktbQI4.mwomIc meld ~ S %, 11 1
It. %ligafh"is. Z&kt. MAW161
Owto.1 21, 011-13(IM11. d. CA. 44. ff.%'Cif.~Suffonj-
by 2U'rq. fArUilk X. M VA
toole) I hr. at .1-190 irk-Ids acid.
i--44ted a- the di-Sa wit (M RIO. pri- (from aq. H1011),
givine A bluish dearactm in sq, w4a, tfntmmt vrith
I I Alt tit" na color. but PeCts Own an intense blue c4m.
t1i%n~o-9w-uitmbmmr on cmrAini; Yields A mdommance Or.
twangroetsilts.
UaWOURNII)a to bog 10% 114416 Virlds at quy(~Iic
*61 that is f6imi"I with she aNw. thun Proving the
Ottioutt. Diamod"tion of l,V,4."It\xIIO)c%IwSw1)1
mW pptn. of the dimso derk. by tnesuis of HAM. from
'AftUy jm:idifird ooln.. Ntlawcd by ttraltntnt of the pl.t.
witlaSnChinalk-SWIl and thefernOTWO1 14~AdSU Ions.
gave IsOlAted as the di-Na
sa whydiam thin Pri-& (frou, &q. Rtolf). giving * bluish
flooremmuce U sq. suba., turning blut-violet with XXIS,
dirtr blue with FeCla; dWa-m-flitrobenrent givro a 'Kit.
m%ulp-midye; IMOts JVC4 , v*jhjW V,.Uw. *-I the Tkitt'1100%
deriv. curt tw liptd. by KC) to thr 1,11,11 W 11101 M11"

a. V.
V-MWW Sd. Refturb
94i^ (J. cpm. cbew)
0e 11
ww .4 hm wKk UL as%
"W dOwIF MW ik IWn.
- W 4 hm at SDO P"
a". of is g. N7
N Md. nk,
ax 1w ,l. tu.
21h 7u AX*b as X
t
0u
dM6=t I WWI= so Iflou, I m1w"
N(Ro
tw No k Its" W"
own*= 1 hr. lm SIL
JUOH
abbis to blft.'- a. I lip
~ cl In
wW emwered wftb

W"'T,
73'. TL, N-. "It arid.;
Drum=
ull, Sol, in HID, ma. In Rio)]; Z~a ~h.
Eal-511.0, --i~ WIT Rol- 4A -ild itcj.
-MA-Adutint the 4 the bi=wte gt:l (h-'Am thr NA "It Ima t~ftxldirh-u plat
~ -11 mm" rd
SwIngly to, in cold %0, !P". 6 'Ston. fla
st4adyizj the 00aed
ult of I In 120 ml-ntO vru added 120 %z1. M%Oli, tbm,
Pvc 7 g of to M grsdually 40 z. 2u dvAt at 33 tv d x rQ
_w mz Ite *1 . e
%nq 7 ks; at 301 and opidibd, vkUlnz lij
cb&mteTj=d as _"d I.?-
ith $)LF-
It
Mn,
7urt4adk4 Ni Hvith
M(7.j4cJl";*ImLHt0
Imud whl 7 au4 ft L-mm uh. trftW,*fth 20
ml, *~Lvt 1OW X. 0SPLU4
WQ IRV , bolated allbe No sag, cr."IMisselft'l-OHko
(SAW, Ajw bftft t* ISO' - Vith
ft mo the
m. ij Tic
mupd.- de rwad f-m-n
"vap tIm &= '
Wne
10M A
2.2 M~Ww in-100 Mg- H.01MW mitb:42.5 irIl
ev HN000milft~ 4t 94--S' 3"Itmea IJA X. 11. U cin be!
7taiutd dircct.)( by traamtut *1 the dry-%.mcued paste cd I
('mm 0-2 malt with Z17.4
30 27'D Ngllwt in I ;~~ 11,0. filtivilmi, addz- cl 39
NZ a QAc ard 16 9 3. b%_U-4 0-5 hr, AlMtkil.
in X-0 InI. '11.10 at tW' and )lmt!zS Is =lm tia A'~' the
ffitwtd!4a. TrImW with ~~Acl(zo
'Y4
MOT
WWI

patt"40 -A T.
tl+
t
w 1701-4.-To 61.9 g. I ar 04,14Y.50, r4ri of M Pvt ~Dmr M. 74'. %nd ism~^A-
ml.nfowas Rwa-Wr~~Gd &
added 4.0 g. ,JaCO,, the vlizt~ rapidly WW 40 min.. Re.'ming iC g U Na Call
moltd. Ettme, and ihe faLratt trexted with 20%(bY vol.) in 100 mi. 14.1c' NA.00~ t, h- dilq -d -~A-q-r;F r~,
NaCi, yield ing 89,5% (11) in (be c~-nled soin ravA9.2% IV. ~!-,o J~m,v
fmm d' tha Gimgc .a iall, wbach %yolied with HsO, MOI
and EtzO, and the cv=biried fUtrate and the residue fmw I in 150 Mi. HO tind the rm~v- bni~ 3 brm ~Phth
the ev - of the waahlr~p kested ? hr lm
kb ~
:i=- ;A
t
th
WW
1
~M
I a2fts ~Muj% FLPPMT 1-1 "t moul cmdenger I tlitm 616M~l
h
.
,
I
1
m 1
W
pp
,
:
L 9m T
e umt rexletits m1red at room tmp. stil
.U _,No no, =%UP
HC, SRVe JM 11. yt,,M rpt. JM. theI rare a lw.!r yklil al the &-Amd and
Plates Umn Rto), w" sparingly Sol. in ; X greater 4vits. of the b'r-prodteft. Th, iYa xsU, vtltn~
=xip p7imu. To 11A X. Il A sah in
3W mrl
40 min
at
B
0 &M 84
RCI i
dded
I !ttj sparingly sol. in Rt0H. fm-x3 a kwxAvJyzL!t. Th--
v
4
0
b
l
d
4
H
.
=
.
m a
am
.
.
6,5-90' IS 1. Zn ditat and the mIxt. stirred 2D -VIA. ILI 00, .
ml.
C.) ir% 15
O
ai
e
mt)i IW%~ ~~,
1 (
anc., in Hei 20 Mi.. P M a. -,;-t (thr dm:z ec=pd
yietdiml 7 1 Z. Heati - 20 g. ]i ga" red color with whkb ~2 M g.: ~- :k!-!,
I
Na saft in OW mL 411% H.&~, 2 bra. -at 108-12 Cooing, added at 5-10' to 1.3 al. 11NO, (d. 1.35) an~d a ml, RIO
and d1g. v ith SM nil. lf%C- VM* a Yellow rPt. WtI6, bented then dild., ftered. and r2ized kith "td. KC3 salln, yiekftz
to 90' w1i b dil. WH,0H, filtmd, atd v~ with bot 2A7 g. K so dn. o7 Ph"-,
HA ykW td OM f. 2.1-0sNCuHJVHj, m. 142.5-3.0'. 11 to soln- eA the TC udt p,,r rr-d z.ihh. 257' 7h~
Na sail (5 1.) and 1.31 S. NaND, in IOD -ni, 1110 added ove. 14 hrar-rd to rrimi man I ju,
0.5 h. at ~-7* to 10 mi- HO In 100 ml. HO end the ras-
P- of the dlam compd. was 3tirredd 1.5 hr3. (the din, Ht0H). Addn. of Nz.NO~ tu t!m mixt.
deriv. fmn yellow prium); tbJj ~pvv a klat color witli fortunkm of the jimter. if tb-- avid 13 M-Avik~,j tm. with
b:- witb resomlzoL FZ4
d
b
h
Tb
I
i
0
H
C
S
H 407,'o HjSC),, 2,Z-0iNCuff,0H, m. 12S.&-9V (fr~-n MeOH),
1
I
-
-
:v,m w
rz
t
e =zPez%
=
Q
uH-(
)j~
W3,
Q;
20"'s
f th
dl
d
lth 8
5
t
d
I h s forrmed in good ficid. U fm-.n3 in Wwu );rW frc4r.
d
N
i
8
b
o
e
. was tren
over
r. at
.
n R cmup
e
y
X.
soln
NR
la with lit alwe
M s3 d the orat
d to Coti
Wd ng at room t= . j
hn..
ut the
aq.
&jM an suml
an
p
1
1d6
IM
t
d1V
f
!
h
b
d
Tl
,
t
v
p
p
' Q
%n
ie
orrmri
ano
o~-
txn
.u.
nap
t
tor
=
reagents v rmpt resorehiol, ~
hlch &%vt A Mae talor. The frocn I i er h3 fm-m tbr nvrm,;&,v vip -cied
.111 4-4 7C
A so-~m AXA-A -1-A M -I- ~.8% 1- 0!
The
Sq
ia
a
a an
ac
m coal*.
ot~ .. ....

BOGDAIIOV, S.V.; KOROIICVA, I.N.
Ommm"Nomm
Research in the field of naphthofuro=. Part 2. 2-uitro-l-naphthyl4aine-
4-9ulfonlo acid and 2-nitro-l-naphthol-4-oulfonio acid. Rhur.ob.khim.23 no.
10;1761-1764 0 153. (HLRA 6:11)
1. Nanahno-Issladovatel'skly Institut orpulcheakikh poliVroduktoy i krasi-
teley im. I.To.Voroxhiloya. (Bulfonio acids)

7_~
I e.
f" Na N rj~ in 25 ful
,
iw t6teq With
W

an or
JID h
will. *Wdcd
;~oww;s oi. 132
~Ixo Wo. 6
H'so-legives ilk a.1104fri-, of I. c4
18" orm with mmisol

(f
oil avoh~j"J
u. xtoll)

AS! '(ii
rti~159'1. om
1 in 35 vA. concil. 112S0, u
IA 25 Wl - IhWii thl! Alix
t4 it-it urft
W~01-11-'O-~ 411d 4(V5 V'6611 GQ(f4ln4
4 the Jblii4 b
fill"l, titato wi..hT Oll- 3MIl
tOmMar Wi
0d'
vrith Pekinve t
10
I
X
97.8
'hot 20
to I
I
n
"M I
n
a O
w
.
n
2
n
n
.
o
ou
h AM44131 'With B^%(

111F.0,
1-3,24
orlI!4;_'
ro-Iji-iiiii-
yi
.
-45
t.
Oli:CU

oj~ij
Ai
he
Ocattill
WAAi2i
Ak A
xides. and
a U
11cli pv
Mimi dil.
timm4 Into %,lot
Ill.2 17.&-
in N"aall f'o r-m s
'Willie
MGM
viii of tilt: d'ej.
J.-Arfo aria C.
1.0 46"
9.
addect 4t 3-4*
MIM4 4 hrs.o
rell Over a Per
oiie, the
to Or with -
sikkil 2brs.,
AM,
.5
ok
14-
C*rrftpm if,
2m."~2
n'90" ww the
tvith N%.:

in tbe mall.
g; O~Mdvh trouM in
-witb'27 ml, 43.8% N4011 ami 73 H, 11-0.
Iit, PON14-11cl, kq:f I fse~ at :20% mul boiled
IAd vw 'cw1ing. K. -No sell, t%N.,dIv% with
1O~s d, I the SQImill
of
g. I awl 1), U g. bowl hr. it 78-M, javea
rjAcjuA'*s.trtaI&I ivith,41il. Na:co" be ited to
A- filtem). 46d, the iiiyt.. m. 113-3V. ta-en ur)

tx
-bka~--
N 4rs~~Ui'=
-(sty1 4(
rl."a W ~
5xitl4XIL: if Nlljlscj~ filaivet"- thor
SAM); ctimplex (&L~!'Fj w2d"';j .it 3-5'~ ta ~V -n1,
J I
-'d :!S4 1:
N;4! 1 qA, CJ 1 3
c-oolL-4 pvz: 4X-5
e,
M., V tt~ci reflumilog "(L-Ads W 23 his.
n
uht~rn~' A st4;h! ITI. -ofil-r . eal!~ wid the ~Irl. Vn
4z flu
im, wit! oall. with BIA RO*il b~ wa,114ig the
l4b-Na--CO"
;wliml fro p 1173 Fs-mn Naoll
livLlpr- tit tbz "t]. ~i'lzt-io3tA rul.-pild addii. f-st)-
t-gisve' C'n watifig
-oi tLtIWO; 23 lash, rrmov:11 61 mlii~'wtrilu-Mwki
! witti
Ali) .-Vto?j)~
'. ~;-- V.-I,
g
'2*13.8-141~' t-nl~,IL!m With !PV~'
M. li C1
(!'Comp. dcriv.' tkcowp. 2A).-
ft-~ux 1110 aud (CILCT.~,, yi-tl,ling iAW, nt 3 F.
yellow, m. vonvil ls~rmort: --I- thau il'
-unc %"I, lorMcd 11 1w rcailctian i'f
Alv~ ir J. Ge,!, CA-P:n- !f;.
C.

21~
-ali~jjtwlj and
mt N"ll gave 7.2 g, di-,Na 1,2-
Wus~fpnalc, needles or, priulls..
-1 and uq
-4w Ion,
14 ntd from
Tll,- NA salt (R) of tht
add (22.3
mw bmwil, 04en cb!llvd rapidly
Ila, E
.7 c. NuCl and 40 toli
TO)II);.Alato ampling -vith rv-
Islil-
d'*Jth Zwmphthol-3,G4sulfonL~
09 in I ~ 12 6 c1r,' INN Oi
di-M,
111IMS (CO13t;!.
with:
`oridj'JsdWed us the di-No Ivh~
Prisms.
4th dil. HC1 guw 2-
W 2 hi~.:v
Ir/Ink'atia# isal4ml a% the di-Na
nwilo (from Aq; 3;tOll), -wilile m-
001mmit,: )Tnow
A duo
as
_'L 'Its kh
U s4 di-Ma z-Al (3.6 moh
' Of 0 a et
4
In rtflunted 10 mill.
VlMi. 2 iMO_.--j..Vt.T9.55?c 1 *0
~:Mbaf
JIM

61

S,

1W

ir Imu

&Vt6
vu

-1"
-
7
.1
.

Ab 6.

7
j
Poe, CA 'Cum.
mimled at 2P
'th Ice pva
ma
dit'lon anti ch3a. h
hi.4 OAI: 016111)
4i m~atvkli~.Mvul Witt; c"Jal.,
jibfai!" a' ppr. of Ca 1,2-
thb,~RhNi~Cul~pi
ia,
01 'aa prektw--, of St--Cl,
57b) iavt U-n~Phlk, a di-
~erqrei~vly 6UMbIg of
I aud
2 JbIt in Kk]
in the
-^t~j VaL
4.4 wt, ptirf Iva, --acbNl;
---- ---
ftbdIi Itift--ji with K-16
.. ..... .. ...

BOGDANOV, S.V.; XORDLVA. I.N.
-
Study of the naphthofuroxan series. Part 5. Sulfonation and
chlorination of naphthofuroxan. Zhur.ob.khim. 26 no.lt264-267
Ja '56&' (KLHk 9-5)
1. Nauchno-iteledovatel'skiy inatitut organicheak1kh poInproduktav
i kresiteley Iment, I.Ye. Vorothilova.
(Naphthofuroxan)

-1.3891da-Tio Ya 3 R. K Z-*,t vff ta~

VIA zol. It
U,~Mtrll Ivilit kr ;ln-ti Pd.
ppt. j

ic yw

7p:---ltf-s fmd YdIc-s-
Bto left bt=,ill-ki ij
vollow netdh ~,, ivlul e the

-rfIXIC: F-115, 'One liqtwi FJ?~,
jai.
6
0
11 trv-mcd NaN
pht"'.
ac,d (DI), and a bromm ivith di:u-1jfil.;.

so!ll --.0 -rtalincnt relded. p),-,0
ke t
Tzi~lrnir avid w'hivlt )4,e-,q viokt colu WI-0)
wilb M; th~ &-au drijv wu.% ;cl;-,!
:i,C03 i~jlm anal t t ated a:z pei Ru:,-~

10'
40~.2*,~Ivl Idth dil fin
ulo-mi-r -v e C
f6 IIJ
ppp,
Ems=

?,tiv Tcid3

-K hr
v
at 15' ori
XOk.: i 1[w t
.
.,
i as~ :mv:3_t;. ~ A ii '_rtmtt,~ a:;n C 4 F_
L~-S-m ~_Irz -1 V` 5. 7
101h sat-31-111(n fave
d

ari
k~s r
L'a
's with M-e
C'mrse-re'l nior, Zral irit'll r,:-

ow- ~"k
11 bmWil cnl~r. The ifl ?.,oj!zej ~j h;t.~j ,c
.1toll the-n ltrentej w,

All
h , u
ft
wt
',S% seed I-Itlab I- CJAJAXM~, IV:N& "It dct=p. 1"'.

bme, Ute--, &pariagly
,
~-
b
b
i
A
T
3-
I'-
3
acm
Ar
d OMSA VO it 1)0
fw, Irb
f4 j6hyd"if K-!Dlr
i$WSW; tIds loses HO 1% 110 ; the anbld
prWint 15
,
vely h Omr- b1slime tompla WaIL-3 With
Y)ddi the t6 emplex of
i
W
a tb-e
m
att gmp =1 fums
bu)O
in " wt

/40

Watt '~ddn'
Ail. Colt it 00* ~j-IdA
With
ism win

DOGDLNOV, S.V.; GORALM, X*V
ISUlfitO OOmpounds of oxy-derivatives of authracene. Xhim. nauka
i prom, 3 no,2t279-280 158. (KIRL 11:6)
10Naudhno-iasledo~atellekiy institut organichaskikh polupro&ukboy
i kraelteley iYA. X~Te.Voroddlova,
(Anttxaeene) (Sulfitee)
04,

AUTHOR: Bogdanov, S. V. 79-26-~-47/69
TITLE- Reduction of a Bisulfite Compound of I-N-aphthol
(Vosstanovleniye bisullfitnogo soyedirienjy,~ i-naftola)
I. 1,2-Dihydronaphttialene-2-gii'~~o Acid
(I. 1,2-Digidronaftalin-2-sullfokislota)
PERIODICAL: Zburnal Obshchey Khimii, 1958, Vol, 28, Nr 1324-1327
(USSR)
ABSTRACT, ks was noticed (ref 1) the bisulfite compound of 1-naphthol
behaves toward hydroxylamine and semicarbazide like a
ketone and converts to the oxime and semicarbazone of the
bi-sulfite compound. For this reasbn the formula
1-axo-1,2,3,4-t.etrahydronaphthalene-3-oulfo acid (formula I)
was suggested for this compound. According to data in
publicationa the reduction of I-oxo-1,2,3,4,-tetr&hydro-
iiLnh.tbalene leadq to I-oxo-1,2,5,4-tetrahydronaphthalene and
to 1,11-dioxy-' 11-ditetralyl. In the reaction of 1-naphthol
with bisiilfit.,b"ideg the bisulfite t~ompound of uaphthol
alsr '12- 11116 "Is 4 -naphthol so.lf o acids form. It wFtq of
interest to investigate also the behavi-our of the bisulfite
Card 1/3 compound of-1-naolithol toward the reducing agents. The

Reduction of a Bisulfite' Compound of I-Naphthol. 79-28-~)-471/69
I. 1,2-;)ihydronapht~ia3.eyie-2-Fxilf'o Acid
result3 showed that this compound on the action of zinc in
diluted acetic acii in the presence of copper sulfate
convertF to Ft mixture of reduction producLs ircia wii.Luti Vie
SodiUM stlt' of the 1,:?-di.hydronaphthelene-2-sulfo acid (I!)
wan Lmu.Lited. 1,2 dihydronaphthalene-2-aulfo acid is cleft
intoalkali liouore and mineral acids in naphthalene Rnd
suifurous acid, nnd on the action of bromine water,,converts
to 4-0-xY-3-broino-l,:>,3,4-tetrahydronaphthalene-2-sulfo-
acid. The latter In acidous medium yipid-3 naphthalene and
-2-bromonaphtbalone, and in alkaline medium naphthalene-2-
sulfo acid. The formation of the 1,2-dihydronaphtlialene-2-
sulfo acid in the reduction of the bisulfite compound of
1-na-Dhthol proves the proposed structure of the latter, i.
9. formula 1. There itre '_'; references, 3 of which are Soviet.
Card 2/3

Reduction of a Bisulfite Compound of I-Naphthol. 79_26-h-A7169
I. 1,2-Whydronaphthalene-2-Sulfo Acid
ASSOCIATION: Hauchiio--;~saledovatellsl:iy,institut organichesk3.1,h
poluproduktov i kraaiteley (Scientific Ron-narch institute
for Organic lhtei~69dliU-Productb and Dyes)
SUBMITTED: ADril 22, 1957
Card 3/3

AUTHOR: Bogdanov, S. V. 79- ~6-'~-46/69
TITLE: Pedi-tion of th~-tlsulfite Compound of 1-Naphthil !,r-d.
of !:,a Oxime 11. (Voss1;anPv).eW)rP.
!-naftola. i yego oksima., 11)
PERT.ODICAL: Zhurnal Obshchey Khimti,, 1958, Volo 26, Nr 5,
pp.p 1326-133? (USSR)
ABSTRACT: Not long ~Ago (ref -1) it waA noticed chat iv Ojs- reauction
of the bieulfite compound of 1-naphthol with zinc in acetic
acid a reaction mixture forms from which the 1,2-,Iinydro-
naphthalene-Z-sulfo acid was isolated (formillm 1). Tne
deposit produced from the reaction sclutinn by addition of
sodium ch-,lorids- c-ontained 76,5 *,V sodium salt, of the
compound (1) and a considerable amount of sodlum sal.t. of
the aiilfo acid, which r(~acl-~d neith,rv- with -odj.n~- nor with
bromine wn"er ana which was resi-stant to ~Jknil
, - - 1.1 -_. L:, . :., -,mo,,d
.. (,_ I ~ M , - un,
liquors alij Rc~dS6 ThIS bail Wa~-
by f raol. i al , -:-ystal.~ization of water ana by b-~dling
with a I., 1-ve. This compound is a tertrakyai-onaphtha-
lenesulfo scid, which on the dehydrataort with sulfur converts
Card 1/-3 to iiaDhthalene-2-sulro t-.Lcid and is. oin mu~E-t be nssuip,"d, a

Reduction of the Bisulfito rompound of 1-Naphthol '19-28-5-AFI/69
and of Its Oxime. 11.
sait of the it2li,4-tetrahydronaphthalene-2-.qulfo acid (I.T)
(yield more than 11 0). its formation tnkes Dlace by
,immediate reduntion of the bisulfite compound, as compound
-1) in not subject to the action of zinc Find acetic acid.
in the reduction of the bisulfite compound of 1-inaphthol
with zinc and acetic acid besides compounds (1) ana (II) the
1-oxy-1,2,3,4-tetrah.vdro)-(31,41-dibydro-)-1,11-dinapht~yl-
3,3'-diculto acid (IIT) is also formedf which can as well
be obtained wizh hydrochloric acid in the place of acetic
acid. The same compound converts to 1,1-dinaphthyl on heating
with sodium hydroxide of sulfuric acid. Tn the reduction of
the oxime of the bisuffite compound of naphthol with zinc
and acetic acid the 1-amino-1,2,3,4-tetrahydro-naphthalene-3-
sulfo acid (V) results. The direction of the bisulfite
compound of 1-naphthol and of its oxime corresponds to the
reduction course of 1-oxo-1,2,3,4-tetrahydronaphthalene and
ol' 1-ts oxime and thus proves tb urlier proposed
struoture formulae of the b-iaulfite compound and of its oxime.
Card 2/3 There are 3 references, 2 of which are Soviet.

Reduotion of the Binulfite Compound of 1-Naphtho) 7q--H-7.A8./69
and of Its Oxime.TT.
ASSOCIATION! Nauchno-i ss I edovate I I skiy A n,,tti tut (irg an iI kzh
poluproduktov i (Scientifle, ~nntitute
for Organic Tatermediate P%-oduets ancl Dyes)
SUBMITTFT): April 2?, 1957
Card A i I

KORCUV, A.I., otv.red.; VMIPM. N.s., sam.otv.red,; BOOANOV, S.V.,
reds; DOKUNINHIN, N,S.0 red.; HASEMIKovA, Tf-.V., R'
6d, W-70VIMO
I.V., red,; XHOMSKIY, I.G*t redo; ZWKIN, V,I,, reds; SHPAK, Ye~Ggt
tekhn.red.
[Organic intermediate products aWI dyes; collected articles]
Organiahaskie poluprodukty i krasiteli; sbornik statei. Moskva,
Gos.nauehno-tekhn.izd-vo khim.lit-ry. No.l. 1959. 238 p.
(MIRA 13:7)
H.suchno-issledovateliskiy inatitut organichaskikh polupro-
duktov i kraBiteley.-
(Dyes and dyeing) (Aromatic compounds)

AUTHORS: Bogdanov, S. V., Gorelik, M. V. SOV/79-29-1-30/74
-- -----------------
TITLE: Investigations in the Field of the Oxy-Derivatives of
Anthracene (Iseledovaniye v oblasti oksiproizvodnykh antra-
tbVMT)-I--. Bisulfite Compounds of the 1-Anthrol and 4-Nitroso-
I-Anthrol (I. Bisullfitnyye soyedineniya I-antrola i 4-nitrozo-
1-antrola)
PERIODICAL,.' Zhurnal obahchey khimii, 1959, Vol 29, Nr ij Pp 136-139 (USSR)
ABSTRACT: The investigation of the properties of the bisulfite compounds
of 1-naphthol and 4-nitroso-,l-naphthol (Refs 1, 2) made it
possible to describe their structure with the formulae (1) and
(11). In the present paper the affiliation products of the
bisulfite to the 1-anthrol and 4-nitroso-l-anthrol are in-
vestigated. This affiliation takes place on the treatment of
the 1-anthrol with boiling sodium bisulfite solution (Ref 3).
.,The product 014H 10 OH.NaHSO 3*3H2 0 obtained by the authors is
stable in neutral and acid medium but is decomposed into
sulfite and 1-anthrol in alkaline med-lum. In the reaction with
hydroxylamine, 3emicarbazide or pheny1hydrazine in acetic
Card 1/3 acid it is converted accordingly into the oxime, semicarbazone,

SOV/79-29-1-30/74
Investigations in the Field of t~e Oxy-Derivatives of Anthracene. I. Bi-
sulfite Compounds of the 1-Anthrol and 4-Nitroso-l-Anthrol
pheny1hydrazone of the bisulfite compound of I-anthrol. This
indicates the presence of a carbonyl group and the formula (III).
The formulae of the oxime, semicarbazone, phenylhydrazone
are presented in the formulae (IV) a, b. The bisulf-ite compound
of 4-nitroso-l-anthrol was obtained by the reaction of 4-nitro-
so-1-anthrol with dissolved sodium bisulfite in the presence
of pyr4dine. Without pyridine the yield decreased from 82 to
6%. Alkali liquors readily split off a sulfite molecule from
the bisulfite compound. With hydroxylamine hydrochloride in
the presence of sodiur, acetate the bisulfite compound of
1,4-anthraquinone dioxime is formed from it. The transition of
the biBUlfite compound of 4-nitroso-i-anthrol into the bi-
sulfite compound of 1,4-anthraquinone dioxime indicates the
affiliation of the bisulfite molecule to the carbon-carbon
double bond (V and VI), yet not to the carbonyl group. It may
be concluded from these results that the bisulfite compounds
of anthrol and of 4-nitrono-l-anthrol resemble by their
structure the corresponding derivatives of the naphthalene
Card 2/3 series. There are 5 references, 4 of which are Soviet.

SOV/79-29-1-30/74
. Investigations in the Field of the Oxy-Derivatives of Anthracene. I. Bi-
, sulfite Compounds of the I-Anthrol and 4-Nitroso-l-Anthrol
ASSOCIkTION- Nauchno-issledovatellskiy institut organicheskikh polupro-
duktov i kras~iteley (Scientific Research Institute of Organic
Intermediate Products and Dyes)
SUBMITTED: November 25, 1957
Card 3/3

AUTHORS: Bogdanov, S. V.P Gorelik, M.. V. SOV/79-29-1-31/74
Investigation in the Field of the Oxy~-Derivatives of
Anthracene (Issledovaniye v oblasti oksiproizvodnykh antr4-
.tsena) II, The Bisulfite Compound of*the 1-Nitroso-2-Anthrol
(11. Bisullfitnoye soyedineniye 1-nitrozo-2-antrola)
PMODICAL: Zhurnal obshchey khimii,,11959, Vol 29, Nr 1, Pp 140-145 (USSR)
ABSTRACT: As Previously.'shown by ~o
~danov (Ref 1), the bisulfite com-
,Pound of 1-nitroso-2-na'~hthol is converted by hydroxylamine
into the bisulfite compound of the 1,02-naphthoquinone dioxime
which, onits part, is capable o:r different transformations.
It- suggested itself to synthesize also the bisulfite compound
of"I-nitroso-2-anthrol and t3'investigate whether in the
anthracene series 'also reactions take place which are charac-
teristic of"the bisulfite compound of I-nit -2 -naphthol
and its'der:Lvat-ivesi.On acidification of thl.7boisulfite
soiutio'n of 1-nitroso-2-anthrol Fieser obtaih~ed the I-amino-2-
anthrol-4-sultoni6 acid-in'small yield (Ref 2), but he did
not-suoceed -in 'separating the bisulfite compound. The authors
were able to obtain the bisulfite compoun d of 1-nitroso-2-
anthrol in a 90% yield, by allowing the do-able quantity of
Card 1/3 sodium bi.3ulfite to actin 1-nitroso-2-anthrol in the presenve.

SOV/79-29-1-31/74
Investigation in the Field of the Oxy-Derivatives of Anthracen6. II. The
Bisulfite Compound of the 1-Nitroso-2-Anthrol
of pyridine. This treatment considerably increased the yield,
as was previously seen with the 4-nitroso-1-anthrol (Ref 3),
and part of the product was separated in the form of a
pyridine salt. This bisu-Ifite compound is unstable in alkaline
medium only, whoro it dooomposec quantitativoly into bisulfite
and 1-nitroso-2-anthrol. On the reduction of this compound
with sulfurous acid or tin chloride the 1-amino-2-anthrol-4-
sulfonic acid is formed, in the reaction with hydroxylamine
the bisulfite compound of 1,2-ar4thraquinone dioxime. The
former transformation shows that the sulfo group in the bi-
sulfite compound of 1-nitroso-2--anthrol is in position 4, and
the latter indicates the presence of a carbonyl group. On the
basis of these facts the structure (I) may be assigned to the
bisulfite compound of 1-nitroso-2-anthrol. Compound (II) is
converted, according to conditions, in alkaline medium into
the 1,2-anthra uinone dioxime (III), the bisulfite compound
of 1,2-anthra-~31,49--furazan (IV) or the 1,2-anthra-(3'p4')-
furazan (V). The two figures show the absorption spectra of
Card 2/3 the compounds to, be compared. There are 2 figures and