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Helvetica Chimica Acta – Vol. 94 (2011)
N-Cyclohexyl-2,5-diphenyl-1,3-dioxol-4-amine (3a): Yield 0.308 g (96%). Pale orange solid. M.p.
116 – 1188. IR: 3440, 3311, 3100, 1733, 1655, 1545, 1256, 1113. 1H-NMR: 1.01 – 2.01 (m, 10 H of Cy); 3.77 –
3.87 (m, CHꢁN); 6.10 (d, 3J ¼ 7.5, NH); 6.30 (s, CH); 7.35 – 7.64 (m, 6 arom. H); 8.10 (d, 3J ¼ 7.4, 4 arom.
H).13C-NMR: 24.68, 24.71, 25.43, 32.85, 32.95 (Cy); 48.24 (CHꢁN); 75.93 (CH); 127.42, 128.65, 128.77,
130.03, 128.95, 133.63 (10 arom. C); 129.34, 135.78 (arom. C); 164.95, 167.37 (C¼C). EI-MS: 321 (1), 273
(2), 82 (4), 58 (44), 42 (100). Anal. calc. for C21H23NO2 (321.41): C 78.47, H 7.21, N 4.36; found: C 78.42,
H 7.14, N 4.33.
N-Cyclohexyl-2,5-bis(4-methylphenyl)-1,3-dioxol-4-amine (3b): Yield 0.328 g (94%). Yellow solid.
M.p. 164 – 1668. IR: 3444, 3292, 2928, 1728, 1658, 1256, 1107. 1H-NMR: 1.09 – 1.98 (m, 10 H of Cy); 2.34,
2.42 (2 s, 2 Me); 3.78 – 3.88 (m, CHꢁN); 6.03 (d, 3J ¼ 7.5, NH); 6.26 (s, CH); 7.18 (d, 3J ¼ 7.8, 2 arom. H);
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7.27 (d, J ¼ 7.8, 2 arom. H); 7.40 (d, J ¼ 8.1, 2 arom. H); 7.97 (d, J ¼ 8.1, 2 arom. H).13C-NMR: 21.13,
21.63 (2 Me); 24.63, 24.67, 25.34, 32.67, 32.79 (Cy); 48.10 (CHꢁN); 75.55 (CH); 126.59 (arom. C); 127.27,
129.21, 129.27, 129.71 (arom. C); 132.95, 138.58, 144.26 (arom. C); 165.07, 167.58 (C¼C). EI-MS: 349
(0.6), 315 (1), 240 (10), 119 (100), 104 (19), 91 (27), 58 (23), 42 (65). Anal. calc. for C23H27NO2 (349.47):
C 79.07, H 7.79, N 4.01; found: C 79.11, H 7.76, N 4.08.
2,5-Bis(4-chlorophenyl)-N-cyclohexyl-1,3-dioxol-4-amine (3c): Yield 0.358 g (92%). White solid.
M.p. 199 – 2018. IR: 3446, 3279, 2930, 2358, 1732, 1657, 1253, 1100. 1H-NMR: 1.10 – 1.98 (m, 10 H of Cy);
3.76 – 3.85 (m, CHꢁN); 5.95 (d, 3J ¼ 8.1, NH); 6.22 (s, CH); 7.36 (d, 3J ¼ 8.4, 2 arom. H); 7.47 – 7.53 (2d,
3J ¼ 8.2, 4 arom. H); 8.10 (d, 3J ¼ 8.4, 2 arom. H).13C-NMR: 24.67, 24.70, 25.39, 32.86, 32.96 (Cy); 48.40
(CHꢁN); 75.39 (CH); 128.85, 129.06, 129.10, 131.14 (arom. C); 129.48, 134.03, 135.13, 140.36 (arom. C),
164.11, 166.69 (C¼C). EI-MS: 390 (0.9), 363 (1), 273 (2), 139 (100), 111 (46), 57 (34), 42 (52). Anal. calc.
for C21H21Cl2NO2 (390.30): C 64.62, H 5.42, N 3.59; found: C 64.55, H 5.34, N 3.62.
N-Cyclohexyl-2,5-bis(2,6-dichlorophenyl)-1,3-dioxol-4-amine (3d): Yield 0.390 g (85%). Pale orange
paste. IR: 3430, 2931, 2854, 1650, 1529, 1489, 1090. 1H-NMR: 1.11 – 1.97 (m, 10 H of Cy); 3.76 – 3.86 (m,
CHꢁN); 5.91 (d, 3J ¼ 7.4, NH); 6.22 (s, CH); 7.38 (2t, 3J ¼ 7.6, 2 arom. H); 7.46 (d, 3J ¼ 7.6, 2 arom. H); 8.02
(d, 3J ¼ 7.2, 2 arom. H).13C-NMR: 24.66, 24.70, 25.39, 32.87, 32.95 (Cy); 48.49 (CHꢁN); 76.59 (CH);
128.85, 129.07, 129.11, 131.14 (arom. C); 129.42, 130.08, 130.45, 140.35 (arom. C); 164.11, 166.69 (C¼C).
EI-MS: 459 (3), 370 (11), 281 (6), 212 (30), 185 (38), 105 (100), 83 (33), 57 (70). Anal. calc. for
C21H19Cl4NO2 (459.19): C 54.93, H 4.17, N 3.05; found: C 54.85, H 4.27, N 3.12.
2,5-Bis(4-bromophenyl)-N-cyclohexyl-1,3-dioxol-4-amine (3e): Yield 0.440 g (92%). Yellow oil. IR:
3449, 3268, 2932, 2354, 1731, 1659, 1249, 1123. 1H-NMR: 1.08 – 1.95 (m, 10 H of Cy); 3.75 – 3.85 (m,
CHꢁN); 5.93 (d, 3J ¼ 7.2, NH); 6.20 (s, CH); 7.39 (d, 3J ¼ 8.4, 2 arom. H); 7.52 (d, 3J ¼ 8.4, 2 arom. H); 7.63
(d, 3J ¼ 6.8, 2 arom. H); 7.93 (d, 3J ¼ 6.8, 2 arom. H).13C-NMR: 24.67, 24.71, 25.39, 32.86, 32.95 (Cy); 48.40
(CHꢁN); 75.45 (CH); 123.34, 127.97 (arom. C); 129.12, 131.24, 132.02, 132.10 (arom. C); 132.46, 134.51
(arom. C); 164.25, 166.59 (C¼C). EI-MS: 479 (1), 370 (14), 316 (4), 199 (8), 183 (66), 97 (34), 83 (50), 71
(53), 57 (100). Anal. calc. for C21H21Br2NO2 (479.20): C 52.63, H 4.42, N 2.29; found: C 52.55, H 4.48, N
2.36.
N-(tert-Butyl)-2,5-diphenyl-1,3-dioxol-4-amine (3f): Yield 0.266 g (90%). Yellow solid. M.p. 144 –
1458. IR: 3435, 3290, 1724, 1655, 1555, 1450, 1263, 1113. 1H-NMR: 1.37 (s, Me3C); 6.02 (br. s, NH);
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6.23 (s, CH); 7.35 – 7.63 (m, 8 arom. H); 8.08 (d, J ¼ 8.1, 2 arom. H).13C-NMR: 28.71 (Me3C); 51.61
(Me3C); 76.06 (CH); 127.45, 128.65, 128.78, 128.91, 129.76 (8 arom. C); 129.39, 135.96 (2 arom. C); 133.60
(2 arom. C); 164.90, 167.38 (C¼C). EI-MS: 295 (0.8), 212 (34), 190 (8), 162 (9), 105 (100), 77 (28), 57
(18). Anal. calc. for C19H21NO2 (295.38): C 77.26, H 7.17, N 4.74; found: C 77.29, H 7.18, N 4.71.
N-(tert-Butyl)-2,5-bis(4-chlorophenyl)-1,3-dioxol-4-amine (3g): Yield 0.345 g (95%). White solid.
M.p. 148 – 1508. IR: 3450, 3291, 1725, 1656, 1555, 1258, 1103. 1H-NMR: 1.36 (s, Me3C); 5.89 (br. s, NH);
6.14 (s, CH); 7.30 (d, 3J ¼ 8.2, 2 arom. H); 7.82 (d, 3J ¼ 8.2, 2 arom. H); 7.83 (d, 3J ¼ 8.4, 2 arom. H); 8.00
(d, 3J ¼ 8.4, 2 arom. H).13C-NMR: 28.76 (Me3C); 51.80 (Me3C); 75.71 (CH); 128.86, 129.07, 129.38, 131.11
(8 arom. C); 127.60, 134.20, 135.08, 140.32 (4 arom. C); 164.09, 166.72 (C¼C). EI-MS: 307 (1), 280 (12),
141 (45), 139 (100), 11 (16), 57 (40). Anal. calc. for C19H19Cl2NO2 (364.27): C 62.65, H 5.26, N 3.85;
found: C 62.64, H 5.32, N 3.83.
N-(tert-Butyl)-2,5-bis(4-methylphenyl)-1,3-dioxol-4-amine (3h): Yield 0.290 g (90%). Pale yellow
solid. M.p. 127 – 1288. IR: 3480, 3291, 1720, 1656, 1555, 1113. 1H-NMR: 1.36 (s, Me3C); 2.34, 2.42 (2 Me);
6.00 (br. s, NH); 6.18 (d, 3J ¼ 7.8, 2 CH); 7.26 (d, 3J ¼ 7.8, 2 arom. H); 7.40 (d, 3J ¼ 7.8, 2 arom. H); 7.96 (d,