Reaction of N,N′-disubstituted 1,4-benzoquinone diimines with sodium arenesulfinates

Article abstract of DOI:10.1134/S1070428015010078

Radical anion 1,6-addition path in the reactions of N,N′-disubstituted 1,4-benzoquinone diimines with sodium arenesulfinates is favored by increase of the electron-donating power of the substituent in the para position of arenesulfinate ion and redox pote

Full text of DOI:10.1134/S1070428015010078

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2015, Vol. 51, No. 1, pp. 42–50. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © S.A. Konovalova, A.P. Avdeenko, A.A. Santalova, G.V. Palamarchuk, V.V. D’yakonenko, O.V. Shishkin, 2015, published in Zhurnal
Organicheskoi Khimii, 2015, Vol. 51, No. 1, pp. 48–56.
Reaction of N,N′-Disubstituted 1,4-Benzoquinone Diimines
with Sodium Arenesulfinates
a
a
a
b
S. A. Konovalova , A. P. Avdeenko , A. A. Santalova , G. V. Palamarchuk ,
b
b, c
V. V. D’yakonenko , and O. V. Shishkin
a
Donbass State Engineering Academy, ul. Shkadinova 72, Kramatorsk, 84313 Ukraine
e-mail: chimist@dgma.donetsk.ua
b
Institute for Single Crystals, National Academy of Sciences of Ukraine,
pr. Lenina 60, Kharkiv , 61001 Ukraine
c
Karazin Kharkiv National University, pl. Svobody 4, Kharkiv, 61022 Ukraine
Received June 14, 2014
Abstract—Radical anion 1,6-addition path in the reactions of N,N′-disubstituted 1,4-benzoquinone diimines
with sodium arenesulfinates is favored by increase of the electron-donating power of the substituent in the para
position of arenesulfinate ion and redox potential of the initial 1,4-benzoquinone diimine.
DOI: 10.1134/S1070428015010078
Adams and co-workers [1–7] previously isolated
only 1,4-addition products, 2-arenesulfonylbenzene-
potentials than 1,4-benzoquinone monoimines. Ac-
cording to [8], this should favor formation of 1,6-ad-
dition products and reduction of the initial diimines.
1
,4-diamines, in the reactions of symmetrical N,N′-di-
mesyl-, N,N′-bis(benzenesulfonyl)-, and N,N′-dibenzo-
yl-1,4-benzoquinone diimines with sodium arenesul-
finates. The product structure was determined only on
the basis of their IR spectra, whereas H NMR data
were not given. N-Substituted 1,4-benzoquinone di-
The goal of the present study was to compare the
reactivity of several classes of N-substituted 1,4-qui-
none diimines containing substituents with different
donor–acceptor properties toward sodium arenesul-
finates. The reactions of N,N′-dimesyl- (1) N,N′-bis-
(arenesulfonyl)- (2a, 2b), N,N′-bis[4-chlorobenzene-
1
imines are characterized by considerably higher redox
Scheme 1.
NHMs
1
,4-Addition
MsNH
SO C H R-4
2 6 4
7
a–7c
Ms
NMs
SO Na
N
2
AcOH
1,6-Addition
SO C H R-4
2 6 4
+
R
MsNH
8a–8c
NMs
1
6a–6c
NHMs
Reduction ([H])
MsNH
9
R = Me (a), MeO (b), F (c).
4
2

REACTION OF N,N′-DISUBSTITUTED 1,4-BENZOQUINONE DIIMINES
43
sulfonylimino(phenyl)methyl]- (3), N-(4-methylben-
zoyl)-N′-tosyl- (4), and N,N′-diaroyl-1,4-benzoquinone
diimines (5a–5c) with sodium arenesulfinates 6a–6e
were carried out at a reactant ratio of 1:2 in acetic
acid. In order to facilitate signal assignment in the
H NMR spectra of the products, the aryl fragments in
the initial compounds contained mainly methyl or
methoxy group in the para position.
Product composition in the reactions of quinone diimines
1
–4 with sodium arenesulfinates 6a–6c (Schemes 1–4)
Product composition, %
Reactant
nos.
1
,4
1,6
6,1
6,3
[H]
1
1
1
1
+ 6a
+ 6b
+ 6c
60
56
65
63
41
73
70
28
20
26
08
15
26
–
–
–
–
–
20
18
27
22
33
27
30
17
–
–
N,N′-Dimesyl-1,4-benzoquinone diimine (1) re-
acted with sodium arenesulfinates 6a–6c to give
mixtures of 1,4- and 1,6-addition products 7a–7c
and 8a–8c and reduction product 9 of the initial qui-
none diimine (Scheme 1). Characteristically, increase
of the electron-withdrawing power of the para-
substituent in sodium arenesulfinate in the series
Me < MeO < F was accompanied by increase of
the yield of 1,4-addition product 7a–7c and decrease
of the fraction of 1,6-addition product 8a–8c (see
table). This is consistent with our assumption [9] that
the 1,6-addition path follows radical anion mechanism
and that 1,4-addition products are formed via nucleo-
philic ionic mechanism.
2
a + 6c
b + 6b
–
–
2
–
–
3
3
4
+ 6a
+ 6b
+ 6b
–
–
–
–
–
20
20
15
Like quinone diimine 1, symmetrical N,N′-bis-
(arenesulfonyl)-1,4-benzoquinone diimines 2a and 2b
reacted with sodium arenesulfinates 6b and 6c to
afford mixtures of 1,4- and 1,6-addition products 10
and 11 and benzenediamines 12a (Scheme 2). In the
reaction with 4-methoxybenzenesulfinate 6b, the frac-
tion of the corresponding 1,4-addition product 10a was
larger (see table).
1
The H NMR spectra of 7a–7c displayed singlets
from two NH protons at δ 8.86–8.95 and 10.13–
The reactions of quinone diimine 3 with sodium
arenesulfinates 6a and 6b were highly regioselective,
and only 1,4-addition products 13a and 13b were
obtained. The reaction mixtures also contained some
amount of reduction product 14 (Scheme 3). According
to published data, increased fraction of 1,6-addition
products would be expected, taking into account higher
redox potential of quinone diimine 3 relative to 1
and 2 [10]. Presumably, steric hindrances created by
1
(
0.20 ppm, a doublet from 3-H at δ 7.87–7.93 ppm
meta coupling), a doublet of doublets from 5-H at
δ 7.46–7.54 ppm, and a doublet from 6-H at δ 7.47–
.54 ppm (ortho coupling). In the H NMR spectra of
,6-addition products 8a–8c we observed one NH sin-
1
7
1
glet at δ 10.18–10.20 ppm and doublets due to 2-H/6-H
and 3-H/5-H at δ 7.16–7.18 and 7.20–7.22 ppm,
respectively.
Scheme 2.
1
NHSO C H R -4
2
6 4
1
,4
1
2
4
-R C H SO NH
SO C H R -4
2 6 4
6
4
2
1
0a, 10b
1
SO C H R -4
2
6 4
N
1
N
SO C H R -4
6b, 6c, AcOH
1,6
2
2
6 4
SO C H R -4
2
6 4
1
4
-R C H SO
6 4 2
N
1
4
-R C H SO NH
6 4 2
2a, 2b
1
1
1a, 11b
2a, 12b
1
NHSO C H R -4
2
6 4
[
H]
1
4
-R C H SO NH
6 4 2
1
1
2
1
2
2
, 12, R = H (a), Me (b); 10, 11, R = H, R = F (a), R = Me, R = MeO (b).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015

4
4
KONOVALOVA et al.
the bulky C(Ph)NSO Ar group prevented the 1,6-ad-
dition path.
The reaction of unsymmetrical N-(4-methylben-
zenesulfonyl)-N′-(4-methylbenzoyl)-1,4-benzoquinone
diimine (4) with sodium 4-methoxybenzenesulfinate
product 19 (Scheme 4). It should be noted that intro-
duction of an ArCO group into the initial quinone
diimine essentially changes the product composition,
both qualitative and quantitative. In particular, the
fraction of the 1,4-addition product considerably
decreases, while the amount of 1,6- and 6,1-addition
products (radical ion mechanism [9]) increases (see
2
(
6b) led to the formation of a mixture of 1,4- (15),
6
,3- (16), 6,1- (17), and 1,6-adducts (18) and reduction
Scheme 3.
H
Ph
N
N
1
,4
Ph
Ph
SO C H Cl-4
2 6 4
SO C H Cl-4
2
6 4
N
N
4
4
-ClC H SO
2
Ph
SO C H R-4
6
4
N
N
N
H
2
6 4
AcOH
1
3a, 13b
H
N
N
[H]
SO C H Cl-4
2 6 4
N
N
4
-ClC H SO
6 4 2
-ClC H SO
2
Ph
6
4
N
H
Ph
3
1
4
R = Me (a), MeO (b).
Scheme 4.
H
4
-MeOC H SO
N
C H Me-4
6 4
6
4
2
1
,4
Ts
O
N
H
3
1
5
H
N
C H Me-4
6 4
6
,3
Ts
Ts
O
3
N
SO C H OMe-4
2
6 4
H
1
6
H
N
N
C H Me-4
6 4
O
Ts
6b, AcOH
6,1
O
4
-MeC H
N
N
6
4
4
SO C H OMe-4
2 6 4
1
7
SO C H OMe-4
2
6
4
1
,6
N
C H Me-4
6
4
Ts
O
N
H
1
1
8
H
[
H]
N
C H Me-4
6 4
Ts
O
N
H
9
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015

REACTION OF N,N′-DISUBSTITUTED 1,4-BENZOQUINONE DIIMINES
45
Scheme 5.
OC(O)Me
H
N
C H R-4
6
4
O
O
O
4
-RC H4
N
H
6
2
0a–20c
H
N
C H R-4
SO Na
N
C H R-4
6 4
6
4
2
O
AcOH
1,4
O
O
+
O
4
-RC H
N
R'
4-RC H4
N
H
6
4
6
SO C H R'-4
2
6 4
5a–5c
6a, 6b, 6d, 6e
2
2
1a, 21b
2a–22c
H
N
C H R-4
6 4
[H]
O
4
-RC H4
N
H
6
6
, R′= Me (a), MeO (b), Cl (d), H (e); 5, 20, 22, R = H (a), Me (b), MeO (c); 21, R = R′ = H (a), MeO (b).
table). The most probable reason is higher redox
potential of the initial quinone diimine due to the pres-
ence of ArCO group [11].
the initial quinone diimine to a larger extent than radi-
cal anion 1,6-addition.
It was quite difficult to determine the structure of
20a–20c on the basis of spectral data. Therefore, their
structure was finally confirmed by X-ray analysis of
2,5-bis(4-methoxybenzamido)phenyl acetate (20c).
According to the X-ray diffraction data (see figure),
The spectral parameters of compounds 15 and 16
unambiguously identify them as 1,4- and 6,3-addition
products, respectively; i.e., the arenesulfonyl group
enters the meta (15) and ortho positions (16) with
1
12
9
14
respect to the ArCO group. The H NMR spectrum
the substituent on C is almost coplanar to the C –C
1
7
2
12 11
of 15 contained a doublet at δ 8.48 ppm (meta cou-
pling, 2-H), a doublet of doublets at 7.98–8.01 ppm
benzene ring [torsion angles C N C C –13.4(2)°
and C C C N 27.0(2)°]. The methoxy group on C
slightly deviates from the aromatic ring plane [torsion
angle C O C C –10.6(3)°]. Analogous substituent
on C is less planar [torsion angles C C N C and
N C C C are 43.1(2) and 31.3(2)°, respectively]. The
nonplanar conformation of the substituents is deter-
mined by steric repulsion between the NH and aromat-
ic hydrogen atoms (shortened contacts N –H···H–C
.12 and N –H···H–C 2.11 Å; sum of the van der
2
3
18 17
2
21
(
5
6-H), and a doublet at δ 7.38 ppm (ortho coupling,
-H). In the downfield region of the spectrum of 16,
2
4
6
21 20
9
14
9
1
8
the doublet at δ 7.98 ppm (ortho coupling) was as-
signed to 6-H, and the 3-H and 5-H protons resonated
as a doublet at δ 7.79 ppm (meta coupling) and a dou-
blet of doublets at δ 7.38 ppm, respectively.
1
8
5
4
1
4
Scheme 5 shows the results of the reactions of
N,N′-diaroyl derivatives 5a–5c with sodium arene-
sulfinates 6a, 6b, 6d, and 6e. Among the examined
N,N′-disubstituted benzoquinone diimines, compounds
2
23
2
1
0
Waals radii 2.34 Å [13]). The acetoxy group on C
adopts +sc-conformation with respect to the C –C
benzene ring [torsion angle C O C O 65.3(2)°].
9
14
1
0
3
15
4
5
a–5c are characterized by the highest redox poten-
tials [12], so that increased fraction of radical anion
addition products (1,6-addition path) should be ex-
pected. However, the reactions of 5a with 6b and 6e at
room temperature gave 1,4-addition products 21a and
Thus, the results of our study provide further sup-
port to the ionic mechanism of 1,4-addition of arene-
sulfinates to quinone imines and radical ion mecha-
nism of the 1,6-addition. Increased electron-donating
power of the substituent in the para position of arene-
sulfinate ion favors the radical anion addition path,
while increased redox potential of 1,4-benzoquinone
diimine favors formation of 1,6-addition products
(radical anion mechanism) and reduction of the initial
quinone diimine.
2
1b, whereas compounds 20a–20c (products of 1,4-ad-
dition of acetate ion) were obtained from 5a–5c in
boiling acetic acid. Also, the corresponding reduction
products, bis-amides 22a–22c were detected. The ob-
served pattern may be rationalized taking into account
that increase of the redox potential favors reduction of
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015

4
6
KONOVALOVA et al.
1
6
C
4
15
O
C
3
5
O
O
1
1
1
9
C
C
10
3
7
1
C
4
C
O
1
8
1
C
2
0
C
N
C
2
1
7
N
2
1
C
12
8
C
C
2
4
C
C
C
9
C
5
2
3
2
1
C
C
C
14
6
C
6
1
3
C
C
O
2
2
C
C
2
O
Structure of the molecule of 2,5-bis(4-methoxybenzamido)phenyl acetate (20c) according to the X-ray diffraction data.
EXPERIMENTAL
The H NMR spectra were recorded on a Varian
VXR-300 spectrometer at 300 MHz using TMS as
internal reference. The purity of initial quinone imines
scribed in [15]. Compound 3 was synthesized by
acylation of benzene-1,4-diamine with the correspond-
ing N-arenesulfonyl(aryl)imidoyl chloride in DMF–
AcOH (1 :3) in the presence of anhydrous sodium
acetate as reported in [10] and subsequent oxidation of
the resulting N-substituted benzene-1,4-diamine with
lead tetraacetate in acetic acid. Compounds 4 [16] and
1
1
, 2a, 2b, 3, 4, and 5a–5c was checked by TLC on
Silufol UV-254 plates; samples were applied from so-
lutions in chloroform, benzene–hexane (10:1) was used
as eluent, and spots were detected under UV light.
5
a–5c [17] were prepared by known methods. The
properties of quinone diimine 4 were consistent with
published data [18]. Sodium arenesulfinates 6a–6e
were synthesized according to [19].
The unit cell parameters and intensities of 12519 re-
flections (3860 independent reflections, Rint = 0.123)
for compound 20c were measured on an Xcalibur-3
N,N′-(Cyclohexa-2,5-diene-1,4-diylidene)dimeth-
diffractometer (MoK irradiation, CCD detector,
α
anesulfonamide (1). Yield 85%, mp 200–201°C.
1
graphite monochromator, ω-scanning, 2θmax = 50°).
Triclinic crystal system; unit cell parameters (21°C):
a = 6.115(3), b = 11.459(4), c = 15.983(3) Å;
α = 106.18(2), β = 92.92(3), γ = 94.94(3)°;
H NMR spectrum* (CDCl ), δ, ppm: E isomer: 3.29 s
3
(
2
6H, Me), 6.90–6.93 d.d (2H, 2-H, 5-H, J = 9.0,
.1 Hz), 7.86–7.90 d.d (2H, 3-H, 6-H, J = 10.2 Hz);
Z isomer: 3.28 s (6H, Me), 6.96–6.98 m (2H, 5-H,
–
3
V = 1068.3(7) Å ; M 434.45; Z = 2; space group P1;
6
1
-H), 7.83–7.84 m (2H, 2-H, 3-H). Found, %: N 10.32,
0.91; S 24.18, 24.57. C H N O S . Calculated, %:
3
–1
dcalc = 1.351 g/cm ; μ(MoK ) = 0.098 mm ;
a
8
10
2
4 2
F(000) = 456. The structure was solved by the direct
method using SHELXTL [14]. Hydrogen atoms were
localized by difference synthesis of electron density
maps, and their positions were refined according to
N 10.68; S 24.45.
N,N′-(Cyclohexa-2,5-diene-1,4-diylidene)diben-
zenesulfonamide (2a). Yield 85%, mp 187–188°C;
1
published data [15]: mp 188°C. H NMR spectrum
the riding model (Uiso = nU ; n = 1.5 for methyl
eq
(
CDCl ), δ, ppm: E isomer: 7.54–8.05 m (10H, Ph),
3
groups, n = 1.2 for other hydrogen atoms). The struc-
2
6.92 d (2H, 2-H, 5-H, J = 2.7 Hz), 8.13–8.14 m (2H,
-H, 6-H); Z isomer: 7.54–8.05 m (10H, Ph), 6.97 d
2H, 5-H, 6-H, J = 3.0 Hz), 8.09 d (2H, 2-H, 3-H,
J = 3.0 Hz).
ture was refined against F by the full-matrix least-
3
(
squares procedure in anisotropic approximation for
non-hydrogen atoms to wR = 0.051 (for 3860 reflec-
2
tions) and R = 0.042 [for 935 reflections with F >
1
4
σ(F)]; goodness of fit S = 0.565. The coordinates of
*
Hereinafter, unprimed locants refer to protons in the former
quinone ring, primed locants refer to protons in the aromatic
rings of the substituents on the nitrogen atoms (if two
nonequivalent aromatic rings are present, protons in one of them
are denoted with primed locants, and those in the other, with
triple primed locants), and double primed locants refer to protons
formerly belonging to arenesulfinate.
atoms and complete set of tabulated bond lengths and
bond angles were deposited to the Cambridge Crys-
tallographic Data Centre (entry no. CCDC 993760).
N,N′-Disubstituted 1,4-quinone diimines 1, 2a, and
b were synthesized according to the procedure de-
2
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015

REACTION OF N,N′-DISUBSTITUTED 1,4-BENZOQUINONE DIIMINES
47
N,N′-(Cyclohexa-2,5-diene-1,4-diylidene)bis-
4-methylbenzenesulfonamide) (2b). Yield 90%,
10a, 10b, 15, 16, 20b, and 20c were isolated in the
pure state by successive crystallizations.
(
mp 204–205°C; published data [15]: mp 206.5–
N,N′-[2-(4-Methylbenzenesulfonyl)benzene-1,4-
diyl]dimethanesulfonamide (7a). H NMR spectrum
1
2
07.5°C. H NMR spectrum (CDCl ), δ, ppm:
1
3
E isomer: 3.05 s (6H, Me), 6.89 m (2H, 2-H, 5-H),
(
DMSO-d ), δ, ppm: 2.39 s (3H, 4″-Me), 3.05 s
6
7
5
.37 d (4H, 2′-H, 6′-H, J = 8.1 Hz), 7.89 d (4H, 3′-H,
′-H, J = 8.1 Hz), 8.12–8.14 m (2H, 3-H, 6-H);
and 3.11 s (3H each, MeSO ), 7.46 d (2H, 2″-H, 6″-H,
2
J = 8.1 Hz), 7.47–7.50 d.d (1H, 5-H, J = 2.1, 9.0 Hz),
.54 d (1H, 6-H, J = 8.7 Hz), 7.81 d (2H, 3″-H, 5″-H,
J = 8.1 Hz), 7.89 d (1H, 3-H, J = 2.7 Hz), 8.87 s and
0.14 s (1H each, NH).
Z isomer: 3.05 s (6H, Me), 6.93 d (2H, 5-H, 6-H,
J = 7.2 Hz), 7.37 d (4H, 2′-H, 6′-H, J = 8.1 Hz), 7.89 d
7
(
4H, 3′-H, 5′-H, J = 8.1 Hz), 8.05 d (2H, 2-H, 3-H,
J = 7.2 Hz).
N,N′-(Cyclohexa-2,5-diene-1,4-diylidene)bis-
N′-(4-chlorobenzenesulfonyl)benzenecarboximid-
1
N,N′-[2-(4-Methoxybenzenesulfonyl)benzene-
1
,4-diyl]dimethanesulfonamide (7b). Yield 16%,
[
1
mp 163–164°C. H NMR spectrum (DMSO-d ), δ,
1
6
amide] (3). Yield 85%, mp 201–202°C. H NMR spec-
ppm: 3.05 s and 3.14 s (3H each, Me), 3.84 s (3H,
MeO), 7.17 d (2H, 2″-H, 6″-H, J = 9.0 Hz), 7.46−
.49 d.d (1H, 5-H, J = 2.1, 9.0 Hz), 7.54 d (1H, 6-H,
J = 9.0 Hz), 7.86 d (2H, 3″-H, 5″-H, J = 9.0 Hz),
.87 d (1H, 3-H, J = 2.7 Hz), 8.86 s and 10.13 s (1H
trum (CDCl ), δ, ppm: 6.88 br.s (4H), 7.43–7.82 m
3
(
(
10H, Ph), 7.48 d (4H, 2′-H, 6′-H, J = 9.0 Hz), 7.93 d
4H, 3′-H, 5′-H, J = 9.0 Hz). Found, %: N 8.25,
7
8
.61; S 9.44, 9.65. C H Cl N O S . Calculated, %:
32 22 2 4 4 2
7
N 8.47; S 9.69.
each, NH). Found, %: N 6.64, 6.27; S 21.75, 22.34.
C H N O S . Calculated, %: N 6.45; S 22.14.
N,N′-(Cyclohexa-2,5-diene-1,4-diylidene)di-
1
5
18
2
7 3
1
benzamide (5a). Yield 87%, mp 140–141°C. H NMR
N,N′-[2-(4-Fluorobenzenesulfonyl)benzene-
,4-diyl]dimethanesulfonamide (7c). Yield 38%,
spectrum (CDCl ), δ, ppm: 6.92 s (4H), 7.46–7.93 m
3
1
(
10H, Ph). Found, %: N 8.78, 8.99. C H N O . Cal-
20 14 4 2
1
mp 183–184°C. H NMR spectrum (DMSO-d ), δ,
6
culated, %: N 8.91.
ppm: 3.08 s and 3.14 s (3H each, Me), 7.47 d (1H,
-H, J = 8.7 Hz), 7.51–7.54 d.d (1H, 5-H, J = 2.1,
.0 Hz), 7.51 d (2H, 2″-H, 6″-H, J = 8.7 Hz), 7.93 d
N,N′-(Cyclohexa-2,5-diene-1,4-diylidene)bis-
6
9
(
(
1
4-methylbenzamide) (5b). Yield 83%, mp 155–
1
57°C. H NMR spectrum (CDCl ), δ, ppm: 2.35 s
3
1H, 3-H, J = 2.1 Hz), 8.00 d (2H, 3″-H, 5″-H, J =
.7 Hz), 8.95 s and 10.20 s (1H each, NH). Found, %:
N 6.11, 6.52; S 22.58, 23.13. C H FN O S . Calculat-
(
8
%
6H, Me), 6.86 s (4H), 7.31 d (4H, 2′-H, 6′-H, J =
.1 Hz), 7.84 d (4H, 3′-H, 5′-H, J = 8.1 Hz). Found,
: N 8.03, 8.31. C H N O . Calculated, %: N 8.18.
8
1
4
15
2
6 3
22
18
2
2
ed, %: N 6.63; S 22.77.
N,N′-(Cyclohexa-2,5-diene-1,4-diylidene)bis-
4-methoxybenzamide) (5c). Yield 68%, mp 128–
N-(4-Methylbenzenesulfonyl)-N,N′-(benzene-
(
1
1,4-diyl)dimethanesulfonamide (8a). Yield 12%,
1
29°C. H NMR spectrum (CDCl ), δ, ppm: 3.84 s
1
3
mp 205–207°C. H NMR spectrum (DMSO-d ), δ,
6
(
6H, Me), 6.88 s (4H), 6.97 d (4H, 2′-H, 6′-H, J =
.1 Hz), 7.70 d (4H, 3′-H, 5′-H, J = 8.1 Hz). Found, %:
N 7.32, 7.55. C H N O . Calculated, %: N 7.48.
ppm: 2.43 s (3H, 4″-Me), 3.10 s and 3.58 s (3H each,
8
MeSO ), 7.16 d (2H, 2-H, 6-H, J = 8.7 Hz), 7.21 d
2
2
2
18
2
4
(
2H, 3-H, 5-H, J = 8.7 Hz), 7.47 d (2H, 2″-H, 6″-H,
J = 8.1 Hz), 7.71 d (2H, 3″-H, 5″-H, J = 8.1 Hz),
Reaction of quinone diimines 1, 2a, 2b, 3, 4, and
5
a–5c with sodium arenesulfinates 6a–6e (general
1
2
0.18 s (1H, NH). Found, %: N 6.85, 6.54; S 23.14,
2.86. C H N O S . Calculated, %: N 6.69; S 22.99.
procedure). A solution of 2 mmol of quinone imine
1
5
18
2
6 3
1
4
6
–5 in 20 mL of glacial acetic acid was heated to 70°C,
mmol of the corresponding sodium arenesulfinate
a–6e was added in one portion, and the mixture was
N-(4-Methoxybenzenesulfonyl)-N,N′-(benzene-
1
1
,4-diyl)dimethanesulfonamide (8b). H NMR spec-
trum (DMSO-d ), δ, ppm: 3.10 s and 3.59 s (3H each,
6
stirred until it became colorless. The mixture was
cooled, water was added until complete precipitation,
and the colorless residue was filtered off and washed
first with cold and then with warm water. A part of the
crude product was recrystallized from acetic acid. The
mother liquor was diluted with water, and the precip-
itate was filtered off. The three crystalline samples
Me), 3.88 s (3H, MeO), 7.16 d (2H, 2-H, 6-H, J =
9
2
9
.0 Hz), 7.20 d (2H, 3-H, 5-H, J = 9.0 Hz), 7.41 d (2H,
″-H, 6″-H, J = 9.0 Hz), 7.75 d (2H, 3″-H, 5″-H, J =
.0 Hz), 10.18 s (1H, NH).
N-(4-Fluorobenzenesulfonyl)-N,N′-(benzene-1,4-
1
diyl)dimethanesulfonamide (8c). H NMR spectrum
1
were analyzed by H NMR. Compounds 7b, 7c, 8a,
(DMSO-d ), δ, ppm: 3.10 s and 3.61 s (3H each, Me),
6
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015

4
7
8
KONOVALOVA et al.
1
.18 d (2H, 2-H, 6-H, J = 9.0 Hz), 7.22 d (2H, 3-H, 5-H,
mp 247°C. H NMR spectrum (DMSO-d ), δ, ppm:
6
J = 9.0 Hz), 7.54 d (2H, 2″-H, 6″-H, J = 8.7 Hz),
6.92 s (4H), 7.48–7.67 m (10H, Ph), 10.13 s (2H, NH).
7
.89 d (2H, 3″-H, 5″-H, J = 8.7 Hz), 10.20 s (1H, NH).
Found, %: N 7.03, 7.38; S 16.35, 16.72. C18
Calculated, %: N 7.21; S 16.51.
H N O S .
16 2 4 2
N,N′-(Benzene-1,4-diyl)dimethanesulfonamide
(
9). Yield 89%, mp 263–264°C; published data [2]:
N,N′-(Benzene-1,4-diyl)bis(4-methylbenzenesul-
fonamide) (12b). Yield 89%, mp 265–266°C;
published data [20]: mp 266°C. H NMR spectrum
1
mp 263–265°C. H NMR spectrum (DMSO-d ), δ, ppm:
2
%
6
1
.95 s (6H, Me), 7.18 s (4H), 9.63 s (2H, NH). Found,
: N 20.41, 20.63. C H N . Calculated, %: N 20.57.
(DMSO-d
7
5
), δ, ppm: 2.33 s (6H, Me), 6.90 s (4H),
.29 d (4H, 2′-H, 6′-H, J = 8.1 Hz), 7.54 d (4H, 3′-H,
′-H, J = 8.1 Hz), 10.04 s (2H, NH). Found, %: N 6.64,
8
12
2
6
N,N′-[2-(4-Fluorobenzenesulfonyl)benzene-1,4-
diyl]dibenzenesulfonamide (10a). Yield 48%,
mp 118–120°C. H NMR spectrum (DMSO-d ), δ,
ppm: 6.99 d (1H, 6-H, J = 8.7 Hz), 7.24−7.27 d.d
1
6.80; S 15.15, 15.62. C H N O S . Calculated, %:
20 20 2 4 2
6
N 6.73; S 15.40.
(
7
1H, 5-H, J = 2.4, 8.7 Hz), 7.42−7.79 m (10H, Ph),
.56 d (2H, 2″-H, 6″-H, J = 8.7 Hz), 7.70 d (1H, 3-H,
J = 2.1 Hz), 7.72 d (2H, 3″-H, 5″-H, J = 8.7 Hz),
.54 br.s and 10.71 s (1H each, NH). Found, %:
N 5.26, 5.40; S 17.41, 17.80. C H FN O S . Calcu-
N,N′-[2-(4-Methylbenzenesulfonyl)benzene-
1,4-diyl]bis[N′-(4-chlorobenzenesulfonyl)benzene-
carboximidamide] (13a). Yield 56%, mp 211–212°C.
1
9
H NMR spectrum (DMSO-d ), δ, ppm: 2.33 s (3H,
6
Me), 7.34 d (2H, 2″-H, 6″-H, J = 8.1 Hz), 7.46 d (1H,
5-H, J = 8.1 Hz), 7.49–7.65 m (10H, Ph), 7.50 d (4H,
24
19
2
6 3
lated, %: N 5.12; S 17.60.
2
2
′-H, 6′-H, J = 8.7 Hz), 7.50–7.54 d.d (1H, 6-H, J =
.1, 8.7 Hz), 7.57 d (2H, 3″-H, 5″-H, J = 8.1 Hz),
N,N′-[2-(4-Methoxybenzenesulfonyl)benzene-
1
,4-diyl]bis(4-methylbenzenesulfonamide) (10b).
1
7.75 d (4H, 3′-H, 5′-H, J = 8.7 Hz), 8.58 d (1H, 3-H,
J = 2.7 Hz), 10.44 d and 10.95 s (1H each, NH).
F o u n d , % : N 7 . 11 , 6 . 8 3 ; S 11 . 9 8 , 11 . 4 8.
C H Cl N O S . Calculated, %: N 6.85; S 11.76.
Yield 27%, mp 159–160°C. H NMR spectrum
(
4
8
DMSO-d ), δ, ppm: 2.34 s and 2.35 s (3H each,
6
′-Me), 3.87 s (3H, MeO), 7.11 d (2H, 2″-H, 6″-H, J =
.7 Hz), 7.19 d (1H, 6-H, J = 9.0 Hz), 7.24–7.27 d.d
3
9
30
2
4
6 3
(
1H, 5-H, J = 2.1, 8.7 Hz), 7.33 d (4H, 2′-H, 6′-H, J =
N,N′-[2-(4-Methoxybenzenesulfonyl)benzene-
8
8
3
.4 Hz), 7.59 d and 7.67 d (2H each, 3′-H, 5′-H, J =
.4 Hz), 7.60 d (1H, 3-H, J = 2.1 Hz), 7.65 d (2H,
″-H, 5″-H, J = 8.7 Hz), 9.33 br.s and 10.62 s (1H
1,4-diyl]bis[N′-(4-chlorobenzenesulfonyl)benzene-
carboximidamide] (13b). Yield 52%, mp 178–180°C.
1
H NMR spectrum (DMSO-d ), δ, ppm: 3.80 s (3H,
6
each, NH). Found, %: N 4.59, 4.80; S 16.05, 16.56.
C H N O S . Calculated, %: N 4.77; S 16.40.
MeO), 7.04 d (2H, 2″-H, 6″-H, J = 8.7 Hz), 7.27–
7.60 m (10H, Ph), 7.48 d (1H, 5-H, J = 8.1 Hz), 7.50 d
2
7
26
2
7 3
(
4H, 2′-H, 6′-H, J = 8.7 Hz), 7.52–7.56 d.d (1H, 6-H,
J = 2.1, 8.7 Hz), 7.62 d (2H, 3″-H, 5″-H, J = 8.7 Hz),
.75 d (4H, 3′-H, 5′-H, J = 8.7 Hz), 8.56 d (1H, 3-H,
N-[4-(Benzenesulfonamido)phenyl]-N-(benzene-
sulfonyl)-4-fluorobenzenesulfonamide (11a). H NMR
1
7
spectrum (DMSO-d ), δ, ppm: 6.90 d (2H, 2-H, 6-H,
6
J = 2.4 Hz), 10.43 d and 10.94 s (1H each, NH).
F o u n d , % : N 6 . 6 2 , 6 . 3 8 ; S 11 . 2 8 , 11 . 7 3.
C H Cl N O S . Calculated, %: N 6.72; S 11.54.
J = 8.7 Hz), 7.11 d (2H, 3-H, 5-H, J = 8.7 Hz), 7.50–
.84 m (10H, Ph), 7.56 d (2H, 2″-H, 6″-H, J = 8.7 Hz),
.75 d (2H, 3″-H, 5″-H, J = 8.7 Hz), 10.76 s (1H, NH).
7
7
3
9
30
2
4
7 3
N,N′-(Benzene-1,4-diyl)bis[N′-(4-chlorobenzene-
sulfonyl)benzenecarboximidamide] (14). Yield 93%,
mp 288–289°C; published data [10]: mp 289°C.
4
-Methoxy-N-[4-(4-methylbenzenesulfonamido)-
phenyl]-N-(4-methylbenzenesulfonyl)benzenesul-
fonamide (11b). H NMR spectrum (DMSO-d ), δ,
ppm: 2.37 s and 2.44 s (3H each, 4-MeC H ), 3.89 s
3H, MeO), 6.85 d (2H, 2-H, 6-H, J = 8.7 Hz), 7.09 d
2H, 3-H, 5-H, J = 8.7 Hz), 7.39 d (2H, 2′-H, 6′-H, J =
.7 Hz), 7.43 d (2H, 2″-H, 6″-H, J = 8.7 Hz), 7.47 d
2H, 2′′′-H, 6′′′-H, J = 8.7 Hz), 7.63 d (2H, 3′′′-H,
1
6
1
H NMR spectrum (DMSO-d ), δ, ppm: 7.45–7.59 m
6
6
4
(
9
(
10H, Ph), 7.54 s (4H), 7.54 d (4H, 2′-H, 6′-H, J =
.0 Hz), 7.65 d (4H, 3′-H, 5′-H, J = 9.0 Hz), 10.71 s
2H, NH).
N-[3-(4-Methoxybenzenesulfonyl)-4-(4-methyl-
(
(
8
(
5
8
1
′′′-H, J = 8.7 Hz), 7.71 d (2H, 3′-H, 5′-H, J =
.7 Hz), 7.71 d (2H, 3″-H, 5″-H, J = 8.7 Hz),
0.68 s (1H, NH).
benzenesulfonamido)phenyl]-4-methylbenzamide
(15). Yield 16%, mp 188–190°C. H NMR spectrum**
1
(DMSO-d
), δ, ppm: 2.36 s (3H, 4′-Me), 2.39 s (3H,
6
1
N,N′-(Benzene-1,4-diyl)dibenzenesulfonamide
*
* In the H NMR spectra of 15–19, triple primed locants refer to
(
12a). Yield 82%, mp 247–248°C; published data [15]:
6 4 2
the 4-MeC H SO substituent.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015

REACTION OF N,N′-DISUBSTITUTED 1,4-BENZOQUINONE DIIMINES
49
4
′′′-Me), 3.86 s (3H, MeO), 7.13 d (2H, 2″-H, 6″-H,
J = 9.0 Hz), 7.34 d (2H, 2′′′-H, 6′′′-H, J = 8.1 Hz),
.34 d (2H, 2′-H, 6′-H, J = 7.8 Hz), 7.38 d (1H, 5-H,
J = 9.0 Hz), 7.71 d (2H, 3′-H, 5′-H, J = 7.8 Hz), 7.76 d
2H, 3″-H, 5″-H, J = 9.0 Hz), 7.87 d (2H, 3′′′-H, 5′′′-H,
J = 8.1 Hz), 7.98–8.01 d.d (1H, 6-H, J = 2.7, 9.0 Hz),
.48 d (1H, 2-H, J = 2.7 Hz), 9.38 s and 10.47 s (1H
7.82 d (2H, 3′-H, 5′-H, J = 8.1 Hz), 10.08 s (2H, NH).
Found, %: N 7.17, 7.48; S 8.26, 8.45. C H N O S.
2
1
20
2
3
7
Calculated, %: N 7.36; S 8.43.
1
2
,5-Bis(benzamido)phenyl acetate (20a). H NMR
(
spectrum (DMSO-d ), δ, ppm: 2.23 s (3H, Me), 7.51–
6
7
7
.98 m (10H, Ph), 7.61 d (1H, 3-H, J = 8.4 Hz), 7.63–
.66 d.d (1H, 4-H, J = 2.7, 8.4 Hz), 7.80 d (1H, 6-H,
8
each, NH). Found, %: N 5.24, 4.96; S 11.60, 11.72.
C H N O S . Calculated, %: N 5.09; S 11.65.
J = 1.8 Hz), 9.96 s and 10.43 s (1H each, NH).
2
8
26
2
6 2
2
,5-Bis(4-methylbenzamido)phenyl acetate
N-[2-(4-Methoxybenzenesulfonyl)-4-(4-methyl-
benzenesulfonamido)phenyl]-4-methylbenzamide
1
(
20b). Yield 70%, mp 223–225°C. H NMR spectrum
(
DMSO-d ), δ, ppm: 2.21 s (3H, Me), 2.39 s (6H,
6
1
(
16). Yield 9%, mp 243–244°C. H NMR spectrum
4′-Me), 7.33 d (2H, 2′-H, 6′-H, J = 8.1 Hz), 7.35 d (2H,
2′′′-H, 6′′′-H, J = 8.1 Hz), 7.59 d (1H, 3-H, J = 9.0 Hz),
7.62−7.65 d.d (1H, 4-H, J = 2.4, 9.0 Hz), 7.78 d (1H,
6-H, J = 1.8 Hz), 7.86 d (2H, 3′-H, 5′-H, J = 8.1 Hz),
7.89 d (2H, 3′′′-H, 5′′′-H, J = 8.1 Hz), 9.85 s and
10.32 s (1H each, NH). Found, %: N 6.80, 7.18.
(
DMSO-d ), δ, ppm: 2.35 s (3H, 4′-Me), 2.41 s (3H,
6
4
′′′-Me), 3.80 s (3H, MeO), 7.01 d (2H, 2″-H, 6″-H,
J = 8.4 Hz), 7.37 d (2H, 2′′′-H, 6′′′-H, J = 8.4 Hz),
7
6
8
.38 d.d (1H, 5-H, J = 2.1, 9.0 Hz), 7.40 d (2H, 2′-H,
′-H, J = 7.5 Hz), 7.55 d (2H, 3′′′-H, 5′′′-H, J =
.4 Hz), 7.64 d (2H, 3′-H, 5′-H, J = 7.5 Hz), 7.79 d
C H N O . Calculated, %: N 6.96.
2
4
22
2
4
(
1H, 3-H, J = 2.4 Hz), 7.81 d (2H, 3″-H, 5″-H, J =
2
,5-Bis(4-methoxybenzamido)phenyl acetate
8
1
.4 Hz), 7.98 d (1H, 6-H, J = 9.0 Hz), 10.03 s and
0.59 br.s (1H, NH). Found, %: N 5.10, 5.22; S 11.48,
1
(
20c). Yield 64%, mp 236–237.5°C. H NMR spec-
trum (DMSO-d ), δ, ppm: 2.22 s (3H, Me), 3.84 s (6H,
11.54. C H N O S . Calculated, %: N 5.09; S 11.65.
6
2
8
26
2
6 2
MeO), 7.06 d (2H, 2′-H, 6′-H, J = 8.4 Hz), 7.08 d (2H,
N-{4-[N-(4-Methoxybenzenesulfonyl)-4-methyl-
benzenesulfonamido]phenyl}-4-methylbenzamide
2
7
6
7
1
′′′-H, 6′′′-H, J = 8.4 Hz), 7.59 d (1H, 3-H, J = 8.7 Hz),
.62–7.65 d.d (1H, 4-H, J = 2.1, 9.0 Hz), 7.77 d (1H,
-H, J = 2.1 Hz), 7.95 d (2H, 3′-H, 5′-H, J = 8.4 Hz),
.98 d (2H, 3′′′-H, 5′′′-H, J = 8.4 Hz), 9.78 s and
0.25 s (1H each, NH). Found, %: N 6.35, 6.91.
1
(
17). H NMR spectrum (DMSO-d ), δ, ppm: 2.21 s
6
(
3H, 4′-Me), 2.35 s (3H, 4′′′-Me), 3.87 s (3H, MeO),
7
6
8
3
7
.26 d (2H, 2″-H, 6″-H, J = 8.7 Hz), 7.33 d (2H, 2′-H,
′-H, J = 7.8 Hz), 7.33 d (2H, 2′′′-H, 6′′′-H, J =
.1 Hz), 7.59 d (2H, 2-H, 6-H, J = 8.1 Hz), 7.61 d (2H,
-H, 5-H, J = 8.1 Hz), 7.75 d (2H, 3′-H, 5′-H, J =
.8 Hz), 7.83 d (2H, 3″-H, 5″-H, J = 8.7 Hz), 7.89 d
C H N O . Calculated, %: N 6.45.
2
4
22
2
6
N,N′-[2-(Benzenesulfonyl)benzene-1,4-diyl]di-
1
benzamide (21a). H NMR spectrum (DMSO-d ), δ,
6
ppm: 7.49–8.04 m (15H, Ph), 7.77 d (1H, 5-H, J =
(
2H, 3′′′-H, 5′′′-H, J = 8.1 Hz), 10.25 s (1H, NH).
8
8
.1 Hz), 8.14–8.17 d.d (1H, 6-H, J = 2.1, 8.4 Hz),
.67 d (1H, 3-H, J = 2.4 Hz), 10.15 s and 10.64 s
N-(4-Methoxybenzenesulfonyl)-4-methyl-N-
[
4-(4-methylbenzenesulfonamido)phenyl]benz-
1
(1H each, NH).
amide (18). H NMR spectrum (DMSO-d ), δ, ppm:
6
2
.23 s (3H, 4′-Me), 2.37 s (3H, 4′′′-Me), 3.88 s (3H,
MeO), 6.99 d (2H, 2″-H, 6″-H, J = 9.0 Hz), 7.09 d
2H, 2′′′-H, 6′′′-H, J = 8.1 Hz), 7.20 d (2H, 2′-H, 6′-H,
J = 7.8 Hz), 7.49 d (2H, 2-H, 6-H, J = 8.7 Hz), 7.52 d
2H, 3-H, 5-H, J = 8.7 Hz), 7.65 d (2H, 3″-H, 5″-H,
J = 9.0 Hz), 7.73 d (2H, 3′-H, 5′-H, J = 7.8 Hz), 7.79 d
2H, 3′′′-H, 5′′′-H, J = 8.1 Hz), 9.83 s (1H, NH).
N,N′-[2-(4-Methoxybenzenesulfonyl)benzene-
1,4-diyl]bis(4-methoxybenzamide) (21b). H NMR
1
(
spectrum (DMSO-d ), δ, ppm: 3.78 s, 3.86 s, and
6
3.88 s (3H each, MeO); 7.04 d (2H, 2′-H, 6′-H, J =
9.0 Hz), 7.09 d (2H, 2′′′-H, 6′′′-H, J = 8.7 Hz), 7.16 d
(2H, 2″-H, 6″-H, J = 8.7 Hz), 7.71 d (2H, 3″-H, 5″-H,
J = 8.7 Hz), 7.79 d (1H, 5-H, J = 8.4 Hz), 7.93 d
(
(
(
2H, 3′-H, 5′-H, J = 9.0 Hz), 8.01 d (2H, 3′′′-H, 5′′′-H,
4
-Methyl-N-[4-(4-methylbenzenesulfonamido)-
J = 8.7 Hz), 8.13–8.17 d.d (1H, 6-H, J = 2.1, 7.8 Hz),
8.60 d (1H, 3-H, J = 2.4 Hz), 10.11 s and 10.43 s
(
phenyl]benzamide (19). Yield 83%, mp 240–241°C.
H NMR spectrum (DMSO-d ), δ, ppm: 2.33 s (3H,
′-Me), 2.37 s (3H, 4′′′-Me), 7.04 d (2H, 2-H, 6-H,
J = 8.7 Hz), 7.31 d (2H, 2′-H, 6′-H, J = 8.1 Hz), 7.34 d
2H, 2′′′-H, 6′′′-H, J = 8.1 Hz), 7.60 d (2H, 3′′′-H,
′′′-H, J = 8.1 Hz), 7.62 d (2H, 3-H, 5-H, J = 8.7 Hz),
1
6
1H each, NH).
4
N,N′-(Benzene-1,4-diyl)dibenzamide (22a).
(
5
Yield 91%, mp 336–338°C; published data [21]:
mp 337–340°C. H NMR spectrum (DMSO-d ), δ,
1
6
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015

5
0
KONOVALOVA et al.
ppm: 7.52–7.99 m (10H, Ph), 7.78 s (4H), 10.27 s
8. Burmistrov, K.S. and Burmistrov, S.I., Vopr. Khim.
Khim. Technol., 1981, no. 65, p. 42.
(
2H, NH).
9
. Konovalova, S.A., Avdeenko, A.P., Pirozhenko, V.V.,
Ledeneva, O.P., and Santalova, A.A., Russ. J. Org.
Chem. 2014, vol. 50, p. 1283.
N,N′-(Benzene-1,4-diyl)bis(4-methylbenzamide)
22b). Yield 82%, mp 340°C. H NMR spectrum
1
(
(
2
5
8
DMSO-d ), δ, ppm: 2.39 s (6H, Me), 7.33 d (4H,
6
1
0. Avdeenko, A.P., Burmistrov, K.S., Dubina, V.L., and
′-H, 6′-H, J = 7.5 Hz), 7.74 s (4H), 7.88 d (4H, 3′-H,
′-H, J = 7.5 Hz), 10.12 s (2H, NH). Found, %: N 7.87,
.28. C H N O . Calculated, %: N 8.13.
Skripets, V.I., Ukr. Khim. Zh., 1980, vol. 46, p. 1081.
1
1. Burmistrov, K.S. and Burmistrov, S.I., Zh. Org. Khim.,
980, vol. 16, p. 1487.
2
2
20
2
2
1
N,N′-(Benzene-1,4-diyl)bis(4-methoxybenzamide)
1
2. Burmistrov, K.S., Doctoral (Chem.) Dissertation,
1
(
(
2
5
7
22c). Yield 35%, mp 336–337°C. H NMR spectrum
Dnepropetrovsk, 1990.
DMSO-d ), δ, ppm: 3.84 s (6H, MeO), 7.07 d (4H,
6
1
1
3. Zefirov, Yu.V., Kristallografiya, 1997, vol. 42, p. 936.
′-H, 6′-H, J = 8.7 Hz), 7.74 s (4H), 7.98 d (4H, 3′-H,
′-H, J = 8.7 Hz), 10.08 s (2H, NH). Found, %: N 7.74,
.49. C H N O . Calculated, %: N 7.44.
4. Sheldrick, G.M., SHELXTL PLUS. PC Version.
A System of Computer Programs for the Determination
of Crystal Structure from X-Ray Diffraction Data.
Rev.5.1, 1998.
2
2
20
2
4
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 1 2015