Activated sterically strained C=N bond in N-Arylsulfonyl-p-quinonemono-and diimines: IX. Synthesis and reactions of N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine

Article abstract of DOI:10.1023/A:1013140330701

N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine as the other N-arylsulfonyl-1,4-benzoquinonimines with an activated C=N bond reacts along 1,2-addition path with alcohols and sodium azide and along 1,2-addition-elimination path with aromatic amines. The higher activity of the C=N bond in the N-arylsulfonyl-1,4-benzoquinonimines is not due to the electronic character of the substituent attached to the ring (Cl, CH₃) but to steric influence resulting in increase in the bond angle C=N-S.

Full text of DOI:10.1023/A:1013140330701

Russian Journal of Organic Chemistry, Vol. 37, No. 8, 2001, pp. 1124 1129. Translated from Zhurnal Organicheskoi Khimii, Vol. 37, No. 8, 2001,
pp. 1183 1188.
Original Russian Text Copyright
,
2001 by Avdeenko, Yusina, Yagupol skii.
Activated Sterically Strained C=N Bond
in N-Arylsulfonyl-p-quinonemono- and Diimines: IX.*
Synthesis and Reactions
of N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine
A. P. Avdeenko1, A. L. Yusina1, L. M. Yagupol,skii2
1Donbass State Machinebuilding Academy, Kramatorsk, 84313 Ukraine
2Institute of Organic Chemistry, Ukrainian National Academy of Sciences, Kiev, Ukraine
Received May 5, 2000
Abstract N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine as the other N-arylsulfonyl-1,4-benzo-
quinonimines with an activated C=N bond reacts along 1,2-addition path with alcohols and sodium azide
and along 1,2-addition elimination path with aromatic amines. The higher activity of the C=N bond in the
N-arylsulfonyl-1,4-benzoquinonimines is not due to the electronic character of the substituent attached to the
ring (Cl, CH3) but to steric influence resulting in increase in the bond angle C=N S.
We formerly studied 2,3,5,6-tetrachloroderivatives
of N-arylsulfonyl-p-quinonimines that had chlorine
atoms in both ortho-positions with respect to C=N
bond and thus possessing activated sterically strained
C=N bond (hereinafter activated C=N bond).
A number of reactions with these bonds proceed
unlike those with ordinary N-arylsulfonyl-p-quinon-
imines with no substituents in positions 3 and 5
[2 7].
would change the activity of the C=N bond in
N-arysulfonyl-2,3,5,6-tetramethyl-1,4-benzoquinon-
imines.
The change of the electron density on a carbon
atom may be followed by 13C NMR spectroscopy:
The downfield shift of the signal ( C) evidences the
reduced electron density on the carbon, and the
upfield shift corresponds to the increase in the elec-
tron density [8]. We studied the 13C NMR spectra of
N-tosyl-1,4-benzoquinonimines Ib i with various
substituents in the quinoid ring and compared them
with the spectrum of N-tosyl-1,4-benzoquinonimine
unsubstituted in the ring (Ia) (Table 1).
The most characteristic reactions of quinonimines
with the activated C=N bond are reactions occurring
at these bonds: 1,2-addition and 1,2-addition elimin-
ation [2, 4, 6, 7].
The high activity of the C=N bond was explained
by increase in the bond angle C=N S due to the
presence of substituents in both ortho-positions with
respect to C=N bond. The X-ray diffraction analysis
of N-4-chlorophenylsulfonyl-3,5-dimethyl-1,4-benzo-
quinonimine confirms the above statement: The angle
C=N S is equal to 132.7 C [5].
X = H (a, c, e), CH3 (b, d), Cl (f i); ¶ = H (a, c),
CH3 (b, d), Cl (e i); Z = H (a, b, g), CH3 (c f), Cl
(h, i); Q = H (a, b, g, h), CH3 (c f), Cl (i).
The high activity of the C=N bond in the N-aryl-
sulfonyl-2,3,5,6-tetrachloro-1,4-benzoquinonimines
might be caused by the changed charge on the C4
carbon due to four electron-acceptor substituents in
the quinoid ring. It was presumable that introduction
into the ring of four electron-donor CH3 groups
In the quinonimine series under consideration the
signal (C4) is the most shifted downfield in
N-tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine
(Id), and the greatest upfield shift of the (C4) signal
*
The preceding communication, see [1].
1070-4280/01/3708-1124$25.00 2001 MAIK Nauka/Interperiodica

ACTIVATED STERICALLY STRAINED C=N BOND: IX
1125
Scheme 1.
Table 1. Chemical shifts ( C, ppm) of C4 carbon in the
13C NMR spectra of N-tosyl-1,4-benzoquinonimines (Ia i)
Compd. no.
(C4)
(C4)
Id
Ic
Ib
Ia
If
Ie
Ig
Ih
Ii
167.85
164.72
164.56
163.64
162.60
162.20
160.01
156.03
149.83
4.21
1.08
0.92
0
1.04
1.44
3.63
7.61
13.81
instead of the expected N,N’-ditosyl-2,3,5,6-tetra-
methyl-1,4-benzoquinonediimine we obtained the
product of its partial hydrolysis, N-tosyl-2,3,5,6-
tetramethyl-1,4-benzoquinonemonoimine (Id).
is observed in the spectrum of N-tosyl-2,3,5,6-tetra-
chloro-1,4-benzoquinonimine (Ii). Thus the electron
density on the C4 carbon in this series is the smallest
in quinonimine Id and the greatest in quinonimine Ii.
The composition and structure of compounds
Id, II were proved by elemental analysis (Table 2)
and IR, 1H and 13C NMR spectra.
In the IR spectrum of compound Id appear the
We previously studied the chemical properties of
quinonimines Ic, e, f, i containing an activated C=N
bond. As compared with unsubstituted in the ring
quinonimine Ia the electron density on the C4 carbon
is greater in tetrachloroderivative p-quinonimine Ii,
slightly greater in p-quinonimines Ie, f, and slightly
lower in p-quinonimine Ic [2 7].
absorption bands at the frequencies 1627, 1596,
1555, 1322, and 1161 cm characteristic respectively
of C=O, C=C, C=N, and SO2 groups.
1
The IR spectrum of compound II contains absorp-
1
tion bands at 3280, 1133, and 1171 Cm character-
istic respectively of NH and SO2 groups.
1
The H NMR spectrum of compound Id contains
The reactivity of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonimine (Id) possessing the lowest electron
density on the C4 carbon was not studied earlier.
the following signals ( , ppm): 7.26 7.88 d.d (4H,
Ts), 2.44 s (3H, Ts), 2.02 d, 2.24 d (12H, CH3 of
quinoid ring).
The synthesis of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonimine (Id) is uncommon, since instead
of benzoquinonediimine forms benzoquinonemono-
imine (Scheme 1).
The 13C and APT NMR spectra of compound Id
are completely consistent with the assumed structure
[ (C4), ppm]: 185.44 (C=O), 167.85 (C=N), 143.26
(C4, Ts), 142.11, 140.06 (C2,3,5,6 of quinoid ring),
140.02 (C1, Ts), 129.40, 126.59 (C2,3,5,6, Ts),
21.52 (CH3, Ts), 18.83, 12.80 (four CH3 groups of
quinoid ring). The magnetic equivalence of carbon
atoms C2, C6 and C3, C5 of quinoid ring, and also of
carbons in the CH3 groups in positions 2,6 and 3,5 of
quinoid ring evidences Z,E isomerization at the
nitrogen atom in quinonimine Id that is fast according
to the NMR time scale.
The nitration of 1,2,4,5-tetramethylbenzene
cleanly provides dinitrodurene [9]. Along the
published procedure of dinitrodurene reduction with
tin(II) chloride we obtained the double salt of tin
chloride and diaminodurene hydrochloride [9].The
attempt to acylate the salt with p-toluenesulfonyl
chloride was unsuccessful. Therefore we prepared
diaminodurene by reduction of dinitrodurene with
hydrazine hydrate on Raney nickel. Diaminodurene
base was acylated with p-toluenesulfonyl chloride in
ethyl ether in the presence of triethylamine.
Reactions of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonemonoimine (Id) with alcohols occur as
1,2-addition affording the products of quinolid struc-
N,N -Ditosyl-2,3,5,6-tetramethyl-1,4-phenylenedi-
amine (II) was oxidized with lead tetraacetate, and
ture:
4-alkoxy-4-(tosylamido)-2,3,5,6-tetramethyl-
2,5-cyclohexadien-2-ones (IIIa, b) (Scheme 2)
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 8 2001

1126
AVDEENKO et al.
Table 2. Yields, melting points, and elemental analyses of compounds Id, II, IIIa, b, IVa, b, V, VIa, b, VIIa, b, VIII
Compd.
no.
Yield,
%
mp, C (solvent
crystallization)
for
Found N, %
Formula
Calculated N, %
Id
II
IIIa
IIIb
IVa
IVb
V
VIa+VIIa
VIb+VIIb
VIII
36
84
68
72
25
40
86
70
62
75
134 (C7H16)
4.40, 4.52
5.73, 5.85
3.95, 3.99
4.02, 4.07
5.45, 5.53
4.50, 4.57
C17H19NO3S
C24H26N2O4S2
C18H23NO4S
C19H25NO4S
C17H19NO
C16H16BrNO
C17H20N4O3S
C23H25NO5S2
C24H27NO5S2
C17H21NO3S
4.42
5.96
4.01
3.86
5.53
4.40
15.56
3.05
2.96
4.39
273 (decomp.) (AcOH)
184 (C6H6+ C 6H14)
148 (C6H6+ C 6H14)
92 (AcOH, reprecipitation)
73 (AcOH, reprecipitation)
60 (decomp.)
(AcOH)
(AcOH)
210 (C6H6)
2.92, 3.01
2.95, 3.06
4.35, 4.40
similar to the products forming in reaction with
alcohol from the other N-arylsulfonyl-1,4-benzo-
quinonimines with the activated C=N bond [2, 5].
d.d (4H, Ts), 4.92 br.s (1H, NH), 2.95 q (2H,
OCH2), 2.42 s (3H, CH3 in Ts), 1.72 d, 1.62 d (12H,
CH3 of quinoid ring), 1.10 t (3H, CH3 of Et).
The heating of compounds IIIa, b to melting point
results in their dealkoxylation to yield the original
quinonimine Id; similar process we have observed
formerly with analogous products [2].
In the 13C NMR spectrum of compound IIIa in a
strong field was observed a characteristic signal of
sp3-hybridized carbon atom in the quinolid structure
[ (C4) 84.60 ppm]; the other signals are fully
consistent with the assumed structure ( C, ppm):
184.12 (C=O), 146.39 (C3,5 of quinolid ring),
143.59 (C4, Ts), 136.86 (C1, Ts), 135.97 (C2,6 of
quinolid ring), 129.16, 127.53 (C2,3,5,6, Ts), 49.67
(CH3O), 21.49 (CH3, Ts), 13.80, 11.42 (CH3 of
quinolid ring).
Scheme 2.
In reaction of quinonimine Id with aromatic
amines we failed to isolate the products of 1,2-addi-
tion: occurred 1,2-addition elimination affording
N-aryl-2,3,5,6-tetramethyl-1,4-benzoquinonimines
(IVa, b) (Scheme 3).
Alk = CH3 (a), C2H5 (b).
In the IR spectra of compounds IIIa, b are present
the characteristic absorption bands of the C=O group
1
in the quinolid ring in the region 1625 1630 cm
Scheme 3.
1
and of NH group at 3180 3250 cm .
1
In the H NMR spectrum of compound IIIa were
observed the following signals: broadened singlet of a
proton from NH group (5.22 ppm), three-proton
singlet of CH3O group (2.84 ppm), two doublets
(1.62 and 1.73 ppm) from 6 protons of the two
magnetically equivalent CH3 groups in positions
2, 6 and from 6 protons of the two magnetically
equivalent CH3 groups in positions 3, 5 of the
quinolid ring, and also from the protons in the tosyl
group( , ppm): 7.12 7.50 d.d (4H), 2.40 s(3H,
CH3). Thus the spectrum is in total agreement with
the assumed structure.
Ar = 4-CH3C6H4 (a), 4-BrC6H4 (b).
IR spectra of compounds IVa, b contain the char-
acteristic absorption bands of C=O, C=C, and C=N
groups of quinoid ring in the regions 1640 1630,
1615 1610, and 1590 1580 cm 1 respectively.
1
1
In the H NMR spectrum of compound IIIb are
In the H NMR spectrum of compound IVa appear
present analogous resonances ( , ppm): 7.20 7.49
the signals corresponding to the assumed structure
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 8 2001

ACTIVATED STERICALLY STRAINED C=N BOND: IX
1127
( , ppm): 6.63 7.13 d.d (4H, 4-CH3C6H4), 2.34 (
3H, 4-CH3C6H4), 2.24 br.s, 1.98 br.d, 1.50 br.s
(12H, CH3 in quinoid ring). It should be noted that
the protons of methyl groups attached to positions
3 and 5, 2 and 6 of the quinoid ring are nonequivalent
unlike those in N-tosyl-2,3,5,6-tetramethyl-1,4-benzo-
quinonemonoimine (Id). The dynamic Z,E-isomeriz-
ation process at the nitrogen in quinonimine IVa is
evidenced by the broadened signals of the protons
corresponding the methyl groups at the quinoid ring.
127.73 (C2,3,5,6, Ts), 129.43, 127.38 (C2,3,5,6 of
quinolid ring), 24.23 (CH3, Ts), 15.23, 11.47 (CH3
of quinolid ring).
The reaction of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonimine (Id) with arylsulfinic acids occurs
in two directions: 6,1- and 1,6-addition affording a
mixture
of
N-tosyl-N-arylsulfonyl-2,3,5,6-tetra-
methyl-1,4-aminophenols (Va, b) and N-tosyl-O-aryl-
sulfonyl-2, 3, 5, 6-tetramethyl-1, 4-aminophenols
(VIIa, b) in 1: 1 ratio (Scheme 5).
The hydrazoic acid adds to quinonimine Id in
1,2-position, as with the other quinonimines with the
activated C N group [4]. The resulting product of
quinolid structure, 4-azido-4-(tosylamido)-2,3,5,6-
tetramethyl-2,5-cyclohexadien-2-one (V) is unstable
and at heating eliminates a molecule of hydrazoic acid
to recover the original quinonimine Id. (Scheme 4).
We observed such a process for the first time.
Scheme 5.
Scheme 4.
Ar = C6H5 (a), 4-CH3C6H4 (b).
Commonly arylsulfinic acids react with N-aryl-
sulfonyl-1,4-benzoquinonimines along the scheme of
1,4- or 1,6-addition, and in the presence of chlorine
in 2 and 6 position of the quinoid ring occurs nucleo-
philic substitution of chlorine by the arylsulfinic rest.
The 1,6-addition of arylsulfinic acid to N-aryl-
sulfonyl-1,4-benzoquinonimines possessing isopropyl
or methoxy groups in 2 and 6 positions [10].
Previously we observed that such quinolid struc-
tures with chlorine atoms in 2 and 6 positions under-
went C4 C2-migration of azido group with
simultaneous nucleophilic substitution of chlorine [4].
In our case the nucleophilic substitution of CH3 group
is impossible and therefore occurs elimination of HN3
molecule.
With N-arylsulfonyl-2,3,5,6-tetrachloro-1,4-benzo-
quinonimines only 1,6-addition was observed [11].
In the case under consideration (Scheme 5) occurred
unusual combination of two simultaneous processes:
6,1- and 1,6-addition.
In the IR spectrum of compound V appear char-
In the IR spectra of the mixture of compounds
VIa, VIIa and VIb, VIIb are present the absorption
bands of OH, NH, and SO2 in the regions 3540
3520, 3280 3260, 1380 1370 and 1175 1170 cm
respectively.
acteristic absorption bands of NH, N3, C=O « SO2
1
groups at 3233, 2082, 1635, 1341 and 1170 cm .
1
1
In the H NMR spectrum of compound V appear
the following signals: broadened singlet of the NH
group proton (5.16 ppm), two doublets (1.71 and
1.79 ppm) from the 12 protons of the four CH3
groups attached to quinolid ring, and the resonances
from tosyl group protons at 7.48 7,69 d.d (4H) and
2.43 s (3H, CH3) ppm in full conformity to the
assumed structure.
In the 13C NMR spectrum of compound V in a
strong field was observed a characteristic signal of
sp3-hybridized carbon atom in the quinolid structure
[ (C4) 94.19 ppm]; the other signals are fully con-
sistent with the assumed structure ( C, ppm): 180.90
(C=O), 146.68 (C4, Ts), 134.90 (C1, Ts), 129.95
1
In the H NMR spectrum of the mixture of com-
pounds VIa, VIIa were observed the following
signals ( , ppm): 9.38 br.s (1H, OH), 8.51 br.s (1H,
NH), 7.93 7.35 m (18H, ArSO2 and Ts), 2.45 s,
2.39 s (6H, CH3 in Ts), 2.02 s (6H, CH3 ortho-posi-
tion to OSO2Ph in compound VIIa), 1.84 s (6H, CH3
meta to OSO2Ph of compound VIIa), 1.82 s (6H,
CH3 meta to OH of compound VIa), 1.59 s (6H, CH3
ortho to OH of compound VIa).
1
In the H NMR spectrum of the mixture of com-
pounds VIb, VIIb were observed the following
signals ( , ppm): 9.30 br.s (1H, OH), 8.74 br.s (1H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 8 2001

1128
AVDEENKO et al.
Scheme 6.
Alk = CH3, i-C3H7.
NH), 7.40 7.91 four d.d (16H, Ts), 2.51 s, 2.43 s
(6H, CH3 in Ts of compound VIIb), 2.49 s (6H, CH3
in Ts of compound VIb), 2.12 s (6H, CH3 ortho to
OTs of compound VIIb), 1.96 s (6H, CH3 meta to
OTs of compound VIIb), 1.95 s (6H, CH3 meta to
OH of compound VIb), 1.72 s [6H, CH3 ortho to
OH of compound VIb).
and 75.4 MHz respectively; TMS was applied as
external reference. Compounds Id, IIIa, b, IVa, b,
V were recorded in CDCl3 solution, compounds
VIa, b, VIIa, b, VIII in DMSO-d6. The character-
istics of compounds obtained are listed in Table 2.
Diaminodurene. To a suspension of dinitrodurene
in 15 ml of ethanol was added 0.2 g of Raney nickel
and then was added dropwise 4 ml of hydrazine
hydrate. The mixture was heated to 60 70 C and
gradually turned transparent and colorless. On
completion of the reduction the catalyst was filtered
off, and ethanol was evaporated on a water bath. The
diaminodurene obtained was washed with water and
dried. mp 155 C [9].
The reaction of quinonimine Id with dialkyl
phosphites resulted only in its reduction to N-tosyl-
2,3,5,6-tetramethyl-1,4-aminophenol (VIII). Amino-
phenol VIII also formed on treatment of quinonimine
Id with sodium dithionite in acetic acid (Scheme 6).
The reduction of quinonimine Id with dialkyl phos-
phites may be ascribed to its high redox potential.
N,N -Ditosyl-2,3,5,6-tetramethyl-1,4-phenylene-
diamine (II). To a solution of 5 mmol of diamino-
durene in 20 ml of ethyl ether was added 10.5 mmol
of p-toluenesulfonyl chloride and then 10 mmol of
triethylamine. The precipitated triethylamine hydro-
chloride was filtered off, the filtrate was evaporated
in a vacuum. The colorless precipitate formed was
washed with water, filtered, dried, and recrystallized
from glacial acetic acid.
Similar process was also observed for N-arylsul-
fonyl-2,3,5,6-tetrachloro-1,4-benzoquinonimines;
however in this case were obtained the phosphoryla-
tion products of quinonimines formed along 6,1- and
1,2-addition [6].
IR spectra of compound VIII contain the absorp-
1
tion bands at 3520, 3278, 1327 and 1168 cm cor-
responding to OH, NH, and SO2 groups respectively.
1H NMR spectrum of compound VIII ( , ppm):
9.00 s (1H, OH), 8.03 s (1H, NH), 7.72 7.49 d.d
(4H, Ts), 2.38 s (3H, CH3 in Ts), 1.99 (6H, CH3
meta to OH), 1.78 s (6H, CH3 ortho to OH) is
consistent with the assumed structure.
N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinon-
imine (Id). To a suspension of 2 mmol of N,N -di-
tosyl-2,3,5,6-tetramethyl-1,4-phenylenediamine (II)
in 5 ml of glacial acetic acid was added 4.06 g of lead
tetraacetate. The solution turned orange. Then was
added several drops of ethylene glycol, the mixture
was stirred, and water was added dropwise till
formed orange precipitate of compound Id. The
precipitate was filtered off, washed with water, dried,
and recrystallized from heptane.
The results of the present research and that per-
formed before [1 7] show that the chief cause govern-
ing the direction of the reactions with N-arylsulfonyl-
1,4-benzoquinonimines possessing two substituents
in ortho-position to the C=N bond is not the
electronic factors but the steric influence leading to
decrease in the C=N S angle.
N-Tosyl-2,3,5,6-tetramethyl-1,4-aminophenol
(VIII). To a solution of 5 mmol of quinonimine Id in
25 ml of boiling glacial acetic acid was added by
portions 0.5 g of sodium dithionite till the solution
was colorless. On cooling to the solution was added
several milliliters of water till complete precipitation
of reaction product VIII. The precipitate was filtered
off, washed with water, dried, and recrystallized from
benzene.
EXPERIMENTAL
IR spectra of compounds synthesized were record-
ed on spectrophotometer UR-20 from KBr pellets.
1H and 13C NMR spectra were registered on spectro-
meter Varian VXR-300 at operating frequencies 300
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 8 2001

ACTIVATED STERICALLY STRAINED C=N BOND: IX
1129
Reaction of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonimine (Id) with alcohols. In 5 ml of an
appropriate alcohol was refluxed for 0.5 h 0.5 mmol
of quinonimine Id. The alcohol was evaporated, the
arising crystalline reaction product was recrystallized
from a benzene hexane mixture.
3 ml of acetic acid was added 0.6 mmol of sodium
arylsulfinate, and the boiling was continued for
10 min. The bright orange color of the solution
turned to pale yellow. On cooling precipitated the
colorless crystalline reaction product containing a
mixture of isomers VI and VII in 1: 1 ratio. The
precipitate was filtered off, washed with water, and
recrystallized from acetic acid. The characteristics of
the isomer mixtures VIa, VIIa, and VIb, VIIb are
given in Table 2.
Reaction of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonimine (Id) with alkyl phosphites. To
1 ml of dialkylphosphite heated to 100 C was added
0.5 mmol of quinonimine. The solution obtained was
heated to 150 C. The color of the solution turned
from orange to pale yellow. The solution was cooled
and left standing for a week. The separated colorless
crystalline product VIII was washed with butanol and
recrystallized from benzene, mp 210 C. Yields in
reaction with dimethyl phosphite 85%, with diiso-
propyl phosphite 79%.
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chloroform was added 0.5 mmol of an aromatic
amine. The mixture was stirred by magnetic stirrer
for 2 h and left overnight. The formed thick mass was
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Reaction of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonimine (Id) with sodium azide. To a
suspension of 0.5 mmol of quinonimine Id in 3 ml of
acetic acid was added 0.15 g of NaN3, and the mix-
ture was stirred by magnetic stirrer. Gradually the
bright orange color of the solution turned to pale
yellow. The precipitated colorless crystalline product
V was filtered off and washed with acetic acid.
10. Nichvoloda, V.M., Cand. Sci. (Chem.) Dissertation,
Dnepropetrovsk, 1986.
Reaction of N-tosyl-2,3,5,6-tetramethyl-1,4-
benzoquinonimine (Id) with sodium arylsulfinates.
To a boiling solution of 0.5 mmol of quinonimine in
11. Avdeenko, A.P., Zhukova, S.A., Menafova, Yu.V.,
and Yusina, A.L., Zh. Org. Khim., 2000, vol. 36, no. 6,
pp. 842 846.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 8 2001