ORDER
REPRINTS
o-PHENYLENEDIAMINE
3443
(Anal. Calcdfor C 16H14N2: %C, 82.020; %H, 6.022; %N, 11.952; Found:
%C, 82.019; %H, 6.020; %N, 11.950).
1
2c H-NMR (CDCl3/TMS): d 7.2–7.7 Complex m, 9H, four o-chlor-
ophenyl protons, four aryl protons andone vinylic proton a-to heteryl ring),
7.88 (d, 1H, vinyþlic proton b-to heteryl ring); MS: m/z (%I): 254 and256
(13.4 and1.5, M corresponding to 35Cl and 37Cl), 253 and255 (14.9 and
4.47, Mꢁ1), 220 (13.4), 219 (100, M-Cl), 218 (20.9), 129 (5.2), 77 (7.5), 65
(8.95), 64 (16.4) etc. (Anal. Calcdfor C 15H11N2Cl: %C, 70.731; %H, 4.352;
%N, 10.997; Found: %C, 70.730; %H, 4.351; %N, 10.995).
2d 1H-NMR (CDCl3/TMS): d 7.14–7.72 (Complex m, 10H, four
p-chlorophenyl protons, four aryl protons andtwo vinylic protons), 12.7
(bs, 1H, -NH); 13C-NMR (CDCl3/TMS): d 111.19, 118.55, 122.16, 128.72,
128.98, 132.92, 133.20, 134.74, 151.56, (six p-chlorophenyl carbons, six aryl
carbons, one imidazole quaternary carbon and two vinylic carbons) etc;
MS: m/z (%I): 256, 254 (14.3, 42.9; M þ 2, Mþ) 255, 253 (39.3, 100;
[(M þ 2)-1, Mꢁ1]), 219 (6), 218 (8), 109 (8.6). (Anal. Calcdfor
C15H11N2Cl: %C, 70.731; %H, 4.352; %N, 10.997; Found: %C, 70.730;
%H, 4.351; %N, 10.995).
2e 1H-NMR (CDCl3/TMS): d 7.1–8.2 (Complex m, 10H, four m-nitro-
phenyl protons, four aryl protons andtwo vinylic protons); MS: m/z (%I):
266 (6.63, M þ 1), 265 (55, Mþ), 264 (100, Mꢁ1), 236 (6.73), 235 (20.78),
234 (34.54), 219 (10.73), 218 (30.8), 217 (16.25), 43 (10.16), 42 (9.74);
HRMS: calculatedfor C 15H11N3Oþ2 ¼ 265.085 amu; found ¼ 265.0859 þ /
ꢁ0.0008 amu. (Anal. Calcdfor C 15H11N2O2: %C, 67.917; %H, 4.179;
%N, 15.840; Found: %C, 67.916; %H, 4.178; %N, 15.839).
1
2f H-NMR (CDCl3/TMS): d 7.21 and7.50 (complex m, 4H, aryl
protons), 7.40, 7.56, 7.72 and7.78 (AB quartet, 2H, vinylic protons, JH-H
3
¼ 16.55 Hz), 7.89, 7.93, 8.22 and8.25 (A 2B2 quartet, 4H, p-nitrophenyl
protons, Jortho ¼ 8.2 Hz); 13C-NMR (CDCl3/TMS): d 115.13, 122.06,
122.57, 124.16, 128.00, 131.90, 142.46, 146.92 and150.60 (six p-nitrophenyl
carbons, six aryl carbons, one imidazole quaternary carbon and two vinylic
carbons); MS: m/z (%I): 266 (10, M þ 1), 265 (55, Mþ), 264 (100, Mꢁ1),
234 (10), 219 (21), 218 (67), 217 (30), 206 (8). (Anal. Calcdfor C 15H11N3O2:
%C, 67.917; %H, 4.179; %N, 15.840; Found: %C, 67.916; %H, 4.178;
%N, 15.839).
1
3a H-NMR (CDCl3/TMS): d 7.12–7.49 (complex m, 9H, four aryl
andfive phenyl protons), 7.57 (s, 1H, vinylic proton), 12.58 (s, 1H, -NH);
13C-NMR (CDCl3/TMS): d 15.30 (CH3), 122.00, 127.51, 127.59, 128.55,
129.32, 130.26, 136.52 and154.00 (six phenyl carbons, six aryl carbons,
one imidazole quaternary carbon and two vinylic carbons); MS: m/z
(%I): 236 (0.14, M þ 2), 235 (2.30, M þ 1), 234 (56.9, Mþ), 233 (100,
Mꢁ1), 232 (10.2), 219 (8.44), 157 (44.32), 155 (8.36), 141 (5.34), 129