984
L. B. Krivdin et al.
chemical shifts, CDCl3, (υ, ppm): 91.82 (CCl3), 130.19 (Co),
Ph C C6H4), 8.56 (s, 1H, N CH); 13C chemical shifts, CDCl3,
130.01 (Cm), 135.20 (Ci), 141.79 (Cp), 164.56 (N CH).
o
o
0
(υ, ppm): 21.69 (CH3), 85.71 (CCl2), 126.92 (C ), 128.34 (C ),
m
p
i
i
128.86 (Cm0), 130.07 (C ), 130.39 (C ), 133.24 (C ), 136.32 (C 0),
0
145.67 (Cp), 167.61 (N CH).
Acknowledgements
Financial support from the Russian Foundation for Basic Research
(Grants No. 05-03-32231 and No. 05-03-97202) is acknowledged.
Second author thanks Russian Science Support Foundation for
financial support (Grant RSSF-2007 for postgraduates).
N-(2-Phenyl-2,2-dichloroethylidene)-4-chlorobenzene
sulfonamide (3). Yield: 95%; mp 104–105 C; IR (KBr, ꢁ, cmꢀ1):
°
1170, 1310 (SO2); 1630 (C N); 1H chemical shifts, CDCl3 (υ,
ppm): 7.35–7.90 (m, 9H, Ph C C6H4), 8.60 (s, 1H, N CH); 13
C
o
0
REFERENCES
chemical shifts, CDCl3, (υ, ppm): 85.70 (CCl2), 127.08 (C ),
m
p
i
129.01 (Co), 129.84 (Cm0), 129.87 (C ), 130.57 (C ), 135.16 (C ),
0
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136.26 (Ci0), 141.33 (Cp), 168.59 (N CH).
General experimental procedure for the synthesis of
N-(2,2-dichloroethylidene)arylsulfonamide (4) and
N-(2,2,2-trichloroethylidene)arylsulfonamides (5–7)
A mixture of dichloroamide (10 mmol) and 1,2-dichloro
ethylene (for the compound 4) or trichloroethylene (for 5–7)
(200 mmol) was boiled under continuous flow of argon until
chlorine evolution stopped (8 h). To obtain pure imines 4–7,
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°
the reaction mixture was allowed to stand at ¾0 C for 24 h.
The residue formed was decanted, washed with CCl4 and
dried in vacuum over P2O5.
N-[2,2-Dichloroethylidene]-4-[4-([-2,2-dichloroethylidene]
aminosulfonyl)phenoxy]-benzenesulfonamide (4). Yield: 85%; mp
145–147 C; IR (KBr, ꢁ, cmꢀ1): 1145, 1330 (SO2); 1635 (C N);
°
1H chemical shifts, CDCl3 (υ, ppm): 6.17 (d, 3J D 6.5 Hz,
2H, CHCl2), 7.21, 7.95 (AA0BB0, 8H, 4,40-C6H4OC6H4), 8.38
(d, J D 6.5 Hz, 2H, N CH); 13C chemical shifts, CDCl3, (υ,
3
ppm): 67.07 (CHCl2); 119.84 (Cm), 131.35 (Co), 132.14 (Ci),
160.72 (Cp), 165.72 (N CH).
N-(2,2,2-Trichloroethylidene)benzenesulfonamide(5). Yield:90%;
mp 89–91 C; IR (KBr, ꢁ, cmꢀ1): 1140, 1320 (SO2); 1620 (C N);
1H chemical shifts, CDCl3 (υ, ppm): 7.61, 8.01 (m, 5H, Ph),
8.48(s, 1H, N CH); 13C chemical shifts, CDCl3, (υ, ppm):
92.15 (CCl3); 128.87 (Co), 129.57 (Cm), 134.51 (Cp), 137.27 (Ci),
164.26 (N CH).
°
7. Møller C, Plesset MS. Phys. Rev. 1934; 46: 618.
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Hettema H, Jensen HJA, Jonsson D, Jørgensen P, Kirpekar S,
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de Meras A, Saue T, Sauer SPA, Schimmelpfennig B, Sylvester-
N-(2,2,2-Trichloroethylidene)-4-methylbenzene
sulfonamide (6). Yield: 88%; mp 94–96 C; IR (KBr, ꢁ, cmꢀ1):
°
1135, 1330 (SO2); 1630 (C N); 1H chemical shifts, CDCl3 (υ,
ppm): 2.46 (s, 3H, Me), 7.38, 7.87 (AA0BB0, 4H, C6H4), 8.45
(s, 1H, N CH); 13C chemical shifts, CDCl3, (υ, ppm): 21.69
(Me); 91.75 (CCl3), 128.66 (Co), 130.15 (Cm), 133.11 (Ci), 146.05
(Cp), 163.76 (N CH).
˚
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N-(2,2,2-Trichloroethylidene)-4-chlorobenzene
sulfonamide (7). Yield: 92%; mp 111–113 C; IR (KBr, ꢁ, cmꢀ1):
°
1140, 1330 (SO2); 1620 (C N); 1H chemical shifts, CDCl3 (υ,
ppm): 7.59, 7.95 (AA0BB0, 4H, C6H4), 8.49 (s, 1H, N CH); 13
C
13. Provasi PF, Aucar GA, Sauer SPA. J. Chem. Phys. 2001; 115: 1324.
Copyright 2007 John Wiley & Sons, Ltd.
Magn. Reson. Chem. 2007; 45: 980–984
DOI: 10.1002/mrc