AVDEENKO, KONOVALOVA
678
22.66 (Me6), 16.71 (Me3). Found, %: Cl 28.05, 28.09.
C14H12Cl3NO3S. Calculated, %: Cl 27.94.
3,5-Dimethyl-4-phenylsulfonylimino-5,6-di-
chloro-2-cyclohexen-1-one (XXXVa). Yield 86%, mp
121122°C. 1H NMR spectrum, d, ppm: 6.41 q (1H, H2),
4.44 d (1H, H6), 2.61 d (3H, Me3), 1.78 s [3H, Me5,
J(H2, Me3) 1.5, J(H2, H6) 1.2 Hz], 7.557.99 m (5H,
Ph). 13C NMR spectrum, d, ppm: 186.73 (C1), 170.18
(C4), 149.03 (C3), 132.46 (C2), 62.88 (C6), 50.92 (C5),
25.22 (Me3), 22.50 (Me5). Found, %: Cl 20.50, 20.53.
C14H13Cl2NO3S. Calculated, %: Cl 20.48.
3,6-Dimethyl-4-tosylimino-2,5,6-trichloro-2-
cyclohexen-1-one (XXVIIb). Yield 88%, mp 162
1
163°C. H NMR spectrum, d, ppm: 6.30 s (1H, H5),
2.22 s (3H, Me3), 1.99 s (3H, Me6), 7.387.94 d.d (4H in
Ts), 2.48 s (3H, Me in Ts). Found, %: Cl 26.86, 26.90.
C15H14Cl3NO3S. Calculated, %: Cl 26.95.
3,6-Dimethyl-4-(3-nitrophenylsulfonyl)imino-
2,5,6-trichloro-2-cyclohexen-1-one (XXVIIc). Yield
93%, mp 128129°C. 1H NMR spectrum, d, ppm: 6.16 s
(1H, H5), 2.23 s (3H, Me3), 2.02 s (3H, Me6), 7.83
8.90 m (4H in Ar). Found, %: Cl 25.10, 25.15.
C14H11Cl3N2O5S. Calculated, %: Cl 24.99.
3,5-Dimethyl-4-tosylimino-5,6-dichloro-2-
cyclohexen-1-one (XXXVb). Yield 86%, mp 148
1
149°C. H NMR spectrum, d, ppm: 6.39 q (1H, H2),
4.43 d (1H, H6), 2.60 d (3H, Me3), 1.78 s [3H, Me5,
J(H2, Me3) 1.5, J(H2, H6) 1.5 Hz], 7.367.85 d.d (4H in
Ts), 2.47 s (3H, Me in Ts). Found, %: Cl 19.75, 19.83.
C15H15Cl2NO3S. Calculated, %: Cl 19.68.
6-Isopropyl-3-methyl-4-phenylsulfonylimino-
2,5,6-trichloro-2-cyclohexen-1-one (XXIXa). Yield
65%, mp 144145°C. 1H NMR spectrum, d, ppm: 6.36 s
(1H, H5), 2.24 m [1H, (CH)6], 2.17 s (3H, Me3), 0.89
1.33 d.d (6H, Me2 in i-Pr), 7.568.04 m (5H, Ph).
13C NMR spectrum, d, ppm: 183.17 (C1), 167.54 (C4),
144.98 (C3), 141.12 (C2), 82.96 (C6), 58.75 (C5), 36.48
(C, CH in i-Pr), 18.89 (Me3), 17.60 (Me in i-Pr), 16.43
(Me in i-Pr). Found, %: Cl 26.08, 26.12. C16H16Cl3NO3S.
Calculated, %: Cl 26.02.
2,6-Dimethyl-4-phenylsulfonylimino-5,6-
1
dichloro-2-cyclohexen-1-one (XXXVIIIa). H NMR
spectrum, d, ppm: Z-isomer: 7.87 q (1H, H3), 4.73 d (1H,
H5), 2.18 d (3H, Me2), 1.89 s [3H, Me6, J(Me2, H3) 1.2,
J(H3, H5) 1.5 Hz], 7.568.07 m (5H, Ph); E-isomer:
6.70 q (1H, H3), 6.20 d (1H, H5), 2.10 d (3H, Me2),
1.94 s [3H, Me6, J(Me2, H3) 1.2, J(H3, H5) 2.1 Hz], 7.56
8.07 m (5H, Ph).
N-Phenylsulfonyl-2,6-dimethyl-3-chloro-1,4-
benzoquinone monoimine (XLa). Yield 62%, mp 162
6-Isopropyl-3-methyl-4-tosylimino-2,5,6-tri-
chloro-2-cyclohexen-1-one (XXIXb). Yield 67%, mp
137138°C. 1H NMR spectrum, d, ppm: 6.38 s (1H, H5),
2.23 m [1H, (CH)6], 2.19 s (3H, Me3), 0.871.33 d.d
(6H, Me2 in i-Pr), 7.387.93 d.d (4H in Ts), 2.48 s (3H,
Me in Ts). Found, %: Cl 25.25, 25.29. C17H18Cl3NO3S.
Calculated, %: Cl 25.16.
1
163°C. H NMR spectrum, d, ppm: 8.01 q (1H, H3),
2.23 s (3H, Me6), 2.15 d [3H, Me2, J(Me2, H3) 1.5 Hz],
7.568.07 m (5H, Ph). Found, %: Cl 11.45, 11.56.
C14H12ClNO3S. Calculated, %: Cl 11.44.
N-Tosyl-2,6-dimethyl-3-chloro-1,4-benzo-
quinone monoimine (XLb). Yield 68%, mp 115117°C.
1H NMR spectrum, d, ppm: 8.02 q (1H, H5), 2.22 s (3H,
Me6), 2.15 d [3H, Me2, J(Me2, H5) 2.1 Hz], 7.38
7.93 d.d (4H in Ts), 2.47 s (3H, Me in Ts). Found, %:
Cl 11.45, 11.56. C15H14ClNO3S. Calculated, %: Cl 10.95.
3-Isopropyl-6-methyl-4-phenylsulfonylimino-
2,5,6-trichloro-2-cyclohexen-1-one (XXXIa). Yield
73%, mp 98100°C. 1H NMR spectrum, d, ppm: 6.25 s
(1H, H5), 3.47 m [1H, (CH)3], 1.98 s (3H, Me6), 1.11
1.22 d.d (6H, Me2 in i-Pr), 7.588.02 m (5H, Ph).
13C NMR spectrum, d, ppm: 181.65 (C1), 166.27 (C4),
152.28 (C3), 138.04 (C2), 64.12 (C6), 57.33 (C5), 32.06
(C, CH in i-Pr), 22.63 (Me6), 19.78 (Me in i-Pr), 18.27
(Me in i-Pr). Found, %: Cl 26.10, 26.15. C16H16Cl3NO3S.
Calculated, %: Cl 26.02.
4-Phenylsulfonylimino-2,6-dimethyl-3,5,6-
trichloro-2-cyclohexen-1-one (XLIIa). Yield 93%, mp
152153°C. 1H NMR spectrum, d, ppm: 6.29 s (1H, H5),
2.27 s (3H, Me2), 1.96 s (3H, Me6), 7.568.07 m (5H,
Ph). 13C NMR spectrum, d, ppm: 185.97 (C1), 163.96
(C4), 142.96 (C2), 142.05 (C3), 64.37 (C6), 56.44 (C5),
22.41 (Me2), 15.62 (Me6). Found, %: Cl 27.96, 28.03.
C14H12Cl3NO3S. Calculated, %: Cl 27.94.
3-Isopropyl-6-methyl-4-tosylimino-2,5,6-tri-
chloro-2-cyclohexen-1-one (XXXIb). Yield 67%, mp
134135°C. 1H NMR spectrum, d, ppm: 6.27 s (1H, H5),
3.47 m [1H, (CH)3], 1.97 s (3H, Me6), 1.121.22 d.d
(6H, Me2 in i-Pr), 7.397.91 d.d (4H in Ts), 2.48 s (3H,
Me in Ts). Found, %: Cl 25.20, 25.25. C17H18Cl3NO3S.
Calculated, %: Cl 25.16.
4-Tosylimino-2,6-dimethyl-3,5,6-trichloro-2-
cyclohexen-1-one (XLIIb). Yield 88%, mp 115116°C.
1H NMR spectrum, d, ppm: 6.31 s (1H, H5), 2.26 s (3H,
Me2), 1.95 s (3H, Me6), 7.387.94 d.d (4H in Ts), 2.47 s
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 5 2006