N-Sulfonylcarbamates from Epichlorohydrin
2219
CH3), 1.90 (3H, CH3); 13C NMR (d, ppm): 17.1, 20.4, 20.6, 27.5, 34.4, 62.2,
73.8, 114.9, 129.9, 131.3, 136.3, 145.9, 149.5, 159.1, 166.1; HRMS [M-H]2:
calcd. 476.0378, found 476.0383.
4c: IR (n, cm21): 3352 (NH), 1763 (C55O), 1716 (C55O), 1648 (C55C),
1
1399–1177 (SO2); H NMR (d, ppm): 9.15 (1H, NH), 5.70 (1H, CH55C),
5.20 (1H, CH-O), 4.90 (2H, CCl3-CH2-O), 4.35 (2H, CH2-O,
2Jab ¼ 12.4 Hz, 3Jax ¼ 6.2 Hz, 3Jbx ¼ 4.3 Hz), 3.55 (2H, CH2-Br,
3
3
2Jab ¼ 12.1 Hz, Jax ¼ 5.9 Hz, Jbx ¼ 4.8 Hz), 2.20 (3H, CH3), 1.95 (3H,
CH3); 13C NMR (d, ppm): 20.4, 27.5, 34.5, 62.1, 73.8, 80.8, 92.9, 114.9,
149.8, 159.2, 165.9; HRMS [M-H]2: calcd. 487.8739, found 487.8753.
4d: IR (n, cm21): 3362 (NH), 1768 (C55O), 1719 (C55O), 1648 (C55C),
1
1396–1172 (SO2); H NMR (d, ppm): 9.30 (1H, NH), 7.35 (5H, arom),
2
5.65 (1H, CH55C), 5.20 (1H, CH-O), 4.25 (2H, CH2-O, Jab ¼ 12.3 Hz,
3Jax ¼ 6.3 Hz, 3Jbx ¼ 4.2 Hz), 3.50 (2H, CH2-Br, 2Jab ¼ 12.1 Hz,
3
3Jax ¼ 5.9 Hz, Jbx ¼ 4.7 Hz), 2.10 (3H, CH3), 1.90 (3H, CH3); 13C NMR
(d, ppm): 20.5, 27.6, 34.3, 62.2, 73.7, 114.8, 121.6, 127.2, 130.1, 149.3,
149.8, 159.5, 166.1; HRMS [M-H]2: calcd. 433.9909, found 433.9917.
4e: IR (n, cm21): 3360 (NH), 1767 (C55O), 1719 (C55O), 1649 (C55C),
1393–1175 (SO2); 1H NMR (d, ppm): 9.00 (1H, NH), 7.20 (4H, arom,
3J ¼ 8.8 Hz), 5.70 (1H, CH55C), 5.25 (1H, CH-O), 4.30 (2H, CH2-O,
2Jab ¼ 12.1 Hz, 3Jax ¼ 6.4 Hz, 3Jbx ¼ 4.3 Hz), 3.55 (2H, CH2-Br,
3
3
2Jab ¼ 12.2 Hz, Jax ¼ 5.8 Hz, Jbx ¼ 4.8 Hz), 2.30 (3H, CH3), 2.15 (3H,
CH3), 1.90 (3H, CH3); 13C NMR (d, ppm): 20.5, 20.9, 27.5, 34.4, 62.1,
73.7, 114.9, 121.5, 130.5, 138.3, 147.6, 149.2, 159.5, 166.0; HRMS [M-
H]2: calcd. 448.0065, found 448.0082.
4f: IR (n, cm21): 3358 (NH), 1769 (C55O), 1719 (C55O), 1649
(C55C), 1396–1174 (SO2); 1H NMR (d, ppm): 9.10 (1H, NH), 7.30
(4H, arom), 5.70 (1H, CH55C), 5.30 (1H, CH-O), 4.30 (2H, CH2-O,
2Jab ¼ 12.3 Hz, 3Jax ¼ 6.4 Hz, 3Jbx ¼ 4.2 Hz), 3.55 (2H, CH2-Br,
3
3
2Jab ¼ 12.1 Hz, Jax ¼ 5.9 Hz, Jbx ¼ 4.7 Hz), 2.15 (3H, CH3), 1.90 (3H,
CH3); 13C NMR (d, ppm): 20.4, 27.6, 34.4, 62.2, 73.8, 114.8, 116.0,
124.0, 146.5, 149.6, 159.9, 160.8, 166.1; HRMS [M-H]2: calcd.
451.9814, found 451.9814.
4g: IR (n, cm21): 3353 (NH), 1768 (C55O), 1719 (C55O), 1649 (C55C),
1
1408–1177 (SO2); H NMR (d, ppm): 9.20 (1H, NH), 7.20 (2H, arom),
2
5.75 (1H, CH55C), 5.25 (1H, CH-O), 4.25 (2H, CH2-O, Jab ¼ 12.4 Hz,
3Jax ¼ 6.4 Hz, 3Jbx ¼ 4.1 Hz), 3.55 (2H, CH2-Br, 2Jab ¼ 12.1 Hz,
3
3Jax ¼ 5.7 Hz, Jbx ¼ 4.7 Hz), 2.15 (3H, CH3), 1.90 (3H, CH3); 13C NMR
(d, ppm): 20.4, 27.5, 34.6, 62.3, 73.8, 114.9, 129.1, 130.5, 133.5, 142.9,
149.3, 159.1, 166.1; HRMS [M-H]2: calcd. 535.8739, found 535.8752.