P. Bertus et al. / Tetrahedron: Asymmetry 10 (1999) 1369–1380
1375
Hz), 4.15 (2H, s), 7.53–7.73 (3H, m), 7.86–7.90 (2H, m). 13C NMR (50 MHz, CDCl3) δ 13.8, 22.3, 22.7,
30.9, 44.3, 66.7, 128.2, 129.3, 134.2, 138.7, 198.2. MS (EI): m/e=255 (10, M+H), 198 (19), 141 (42).
4.2.3. Cyclohexyl-2-phenylsulfonyl-ethan-1-one 4
1
A white solid (2.4 g, 69%): mp 89°C. IR (CHCl3): 1710, 1310, 1150 cm−1. H NMR (200 MHz,
CDCl3) δ 1.10–1.40 (5H, m), 1.60–1.90 (5H, m), 2.50–2.70 (1H, m), 4.20 (2H, s), 7.5–7.7 (3H, m), 7.88
(2H, d, J=7.0 Hz). 13C NMR (50 MHz, CDCl3) δ 25.2, 25.5, 27.8, 51.4, 64.7, 128.3, 129.2, 134.1, 138.9,
201.2. MS (EI) m/e=267 (4, M−H+), 141 (18), 124 (66).
4.2.4. Chloro-1-phenylsulfonyl-propan-2-one 5
1
A white solid (1.4 g, 60%): mp 48°C. IR (CHCl3): 1720, 1310, 1160 cm−1. H NMR (200 MHz,
CDCl3) δ 4.39 (4H, s), 7.58–7.78 (3H, m), 7.89–7.94 (2H, m). 13C NMR (50 MHz, CDCl3) δ 48.7, 64.1,
128.3, 129.5, 134.6, 138.1, 190.2. MS (EI): m/e=232 (9, M+), 183 (35), 141 (85).
4.2.5. (Phenylsulfonyl)tridecan-2-one 6
1
A white solid (2.2 g, 50%): mp 74°C. IR (CHCl3): 1725, 1320, 1160 cm−1. H NMR (200 MHz,
CDCl3) δ 0.87 (3H, t, J=6.3 Hz), 1.23 (18H, s), 1.57 (2H, m), 2.69 (2H, t, J=7.2 Hz), 4.14 (2H, s),
7.53–7.72 (3H, m), 7.85–7.90 (2H, m). 13C NMR (50 MHz, CDCl3) δ 14.0, 22.6, 23.0, 28.7, 29.2, 29.5,
31.8, 44.4, 66.7, 128.2, 129.2, 134.2, 138.5, 198.0.
4.2.6. (Phenylsulfonyl)pentadecan-2-one 7
1
A white solid (2.5 g, 52%): mp 75°C. IR (CHCl3): 1710, 1320, 1160 cm−1. H NMR (200 MHz,
CDCl3) δ 0.87 (3H, t, J=6.4 Hz), 1.24 (2H, s), 1.54 (22H, m), 2.69 (2H, t, J=7.2 Hz), 4.14 (2H, s),
7.53–7.72 (3H, m), 7.85–7.90 (2H, m). 13C NMR (50 MHz, CDCl3) δ 14.1, 22.6, 23.1, 28.8, 29.3, 29.6,
32.0, 44.4, 66.7, 128.2, 129.3, 134.2, 138.7, 198.2.
4.2.7. (Phenylsulfonyl)heptadecan-2-one 8
1
A white solid (4.2 g, 41%): mp 77°C. IR (CHCl3): 1710, 1320, 1160 cm−1. H NMR (200 MHz,
CDCl3) δ 0.87 (3H, t, J=6.5 Hz), 1.25 (25H, s), 1.57 (2H, m), 2.69 (2H, t, J=7.2 Hz), 4.14 (2H, s),
7.53–7.72 (3H, m), 7.85–7.90 (2H, m). 13C NMR (50 MHz, CDCl3) δ 14.0, 22.6, 23.0, 28.7, 29.2, 29.6,
31.8, 44.4, 66.7, 128.2, 129.2, 134.2, 138.6, 198.2.
4.2.8. Phenyl-2-phenylsulfonyl-ethan-1-one 9
1
A white solid (2.6 g, 76%): mp 100°C. IR (CHCl3): 1700, 1320, 1160 cm−1. H NMR (200 MHz,
CDCl3) δ 4.77 (2H, s), 7.47–7.74 (6H, m), 7.90–8.00 (4H, m). 13C NMR (50 MHz, CDCl3): δ 63.2,
128.4, 128.7, 129.1, 134.1, 134.2, 135.5, 138.6, 187.9. MS (EI): m/e=260 (0.5, M+), 196 (45), 105 (100).
4.2.9. p-Chlorophenyl-2-phenylsulfonyl-ethan-2-one 10
A white solid: mp 118°C. IR (CHCl3): 1690, 1330, 1170 cm−1. 1H NMR (200 MHz, CDCl3) δ 4.73
(2H, s), 7.28–7.70 (5H, m), 7.87–7.94 (4H, m). 13C NMR (50 MHz, CDCl3) δ 63.5, 128.4, 129.2, 130.6,
133.9, 134.3, 138.5, 141.0, 186.7. MS (EI): m/e=294 (0.9, M+), 139 (100), 77 (54).
4.2.10. p-Fluorophenyl-2-phenylsulfonyl-ethan-2-one 11
A white solid: mp 115°C. IR (CHCl3): 1670, 1310, 1160 cm−1. 1H NMR (200 MHz, CDCl3) δ 4.73
(2H, s), 7.14–7.75 (5H, m), 7.89–8.06 (4H, m). 13C NMR (50 MHz, CDCl3) δ 63.5, 128.4, 129.2, 132.0,
132.2, 134.2, 138.5, 186.3. MS (EI): m/e=278 (0.5, M+), 123 (100), 77 (50).