General Papers ARKIVOC 2002 (i) 71-75
Azoxybenzene (3a). mp 35-36 oC (lit.14 36 oC). Bis-2-chloroazoxybenzene (3b). Red solid, mp 114-115 OC (lit.6 58-59 0C. IR (KBr) . 1619 (N=N), 776 and 730 cm-1 (o-substitution); 1H NMR (d6-acetone) d 6.99-7.01 (1 H, m), 7.21-7.22 (1 H, m), 7.44-7.46 (1 H, m), 7.58-7.62 (3 H, m), 8.22 (1 H, d, J= 8.2 Hz). 13C NMR (d6-acetone) d 116.3, 118.4, 124.5, 125.9, 126.1, 126.8, 127.6, 128.9, 130.7, 125.6. 136.3, 141.6. (Found: C, 54.1; H, 3.2; 10.5. C12H8N2OCl2 requires C, 54.0; H, 3.0; N, 10.5). Bis-3-chloroazoxybenzene (3c). Light yellow solid, mp 105-106 OC (lit.6 96-97 oC). Bis-4-chloroazoxybenzene (3d). Light yellow solid, mp 158-159 OC (lit.6158 OC). Bis-4-methylazoxybenzene (3e) mp 63-65 oC (lit14 66-68 oC) Bis-4-methoxyazoxybenzene (3f) mp 115-116 oC (lit.15116-118 oC) Bis-4-phenylazoxybenzene (3g). Yellow solid, mp 212-214 oC. IR (KBr) .: 3056, 3033, 1598, 1481, 1461, 1443, 843, 762 cm-1. 1H NMR (CDCl3) d 7.41 (m, 2 H), 7.51 (m, 4 H), 7.68 (t, J =
8.8 Hz, 1 H), 7.75 (d,d, J 1 = 8.8 Hz, J2 = 7.6 Hz, 4 H), 8.35 (d, J = 8.8 Hz, 2 H), 8.43 (d, J = 8.8 Hz, 2 H). 13C NMR (CDCl3) d 122.9, 126.3, 127.2, 127.4, 127.5, 127.9, 128.3, 129.0, 129.1, 139.6, 140.2, 142.4, 143.3, 144.6, 147.5. Calcd for C24H18N2O: C, 82.3; H, 5.2; N, 8.0. Found: C. 82.1; H, 5.2; N, 7.9. 4-Carboxy-3-chloroazoxybenzene (3i). Brown solid, mp 290oC (decom). IR (CDCl3) . 3410 (br), 2975, 1707, 1600, 1465, 1249, 1045, 831, 757. IH NMR (DMSO-d6) d 7.72 (d, J = 8.60, 1 H), 7.79 (d, J = 8.8 Hz, 1 H), 8.21 (d, J = 8.8 Hz, 1 H), 8.34 (d, J = 8.6 Hz, 1 H), 8.52 (s, 1 H), 8.57 (s, 1 H), Anal. Calcd for C. Calcd. For C14H7N2O5Cl2: C, 47.5; H, 2.0; N, 7.9. Found: C, 47.6; H, 1.9; N, 7.8.- Azoxy-1-pyrene (3j). Yellow solid, mp 240-242 oC. IR (KBr) .: 3037, 1594, 1499, 1154, 1022, 838, 783 cm-1. 1H NMR (CDCl3 d 8.09 (7.6, Hz 1 .), 8.18 (m, 5 .), 8.27-8.37 (m, 8 H), 8.67 (d, J = 8.8 Hz, 1 H), 8.78 (d, J = 8.8 Hz, 1 H), 8.91 (d, J = 8.8 Hz, 1 H), 9.78 (d, J = 8.8 Hz, 1 H). Anal. Calcd for C. Calcd for C32H18N2O; C, 86.1; H, 4.1:, N, 6.3. Found: C, 86.2; H, 4.2; N, 6.4. Bis-(3,4-dimethyl)azoxybenzene (3k). Yellow solid, mp 141.-142 oC. IR (CDCl3) . 3018, 2969, 2918, 1609, 1491, 1465, 1317, 867, 821. 1H NMR (CDCl3) d 2.34 (s, 3 H), 2.35 (s, 3 H), 2.36 (s, 3 H), 2.38 (s, 3 H), 7.24 (d, J = 8.4 Hz, 2 H), 8.03 (m, 3 H), 8.09 (s, 1 H). 13C NMR (CDCl3) d 19.6, 19.8, 19.9, 20.0, 119.6, 122.9, 123.0, 126.8, 129.7, 129.8, 129.7, 129.8, 136 (3l):.8, 137.2, 138.7, 140.5, 142.2, 146.4. Calcd for C. Calcd for C16H18N2O: C, 75.6; H, 7.1; N, 11.0. Found: C. 75.7; H, 7.2; N, 10.9. (2,4-Dimethyl)azoxybenzene (3l). Colorless crystals mp .56-57.5oC. 1H NMR (CDCl3) d 2.35 (s, 6 H), 2.38 (s, 3 H), 2.48 (s, 3 H), 7.08 (d, J = 8.4 Hz, 2 H), 7.12 (s, 2 H), 7.56 (d, J = 8.8 Hz, 1 H), 8.12 (d, J = 8.4 Hz, 1 H). 13 C NMR (CDCl3) d 18.9, 19.0, 21.5, 21.7, 122.0, 124.0, 127.0, 127.4, 131.4, 131.8, 132.7, 135.1, 129.2, 140.5, 140.9, 147.9. Anal. Calcd for C16H18N2O: C, 75.6; H, 7.1; N, 11.0. Found: C. 75.7; H, 7.2; N, 10.9. ISSN 1424-6376 Page 74 ©ARKAT USA, Inc
