4
Z. ZHOU AND X. HE
7.63 (d, J ¼ 8.2 Hz, 2H), 7.35 (d, J ¼ 8.2 Hz, 2H), 3.73 (t, J ¼ 16.4, 10.8, 5.6 Hz, 1H), 5.13 (dd, J ¼ 18.2, 13.6 Hz, 2H),
J ¼ 4.7 Hz, 4H), 2.98 (t, J ¼ 4.7 Hz, 4H), 2.44 (s, 3H). 13C
4.62 (s, 1H), 3.60 (s, 2H), 2.43 (s, 3H). 13C NMR (125 MHz,
CDCl3) d (ppm): 143.6, 137.0, 133.1, 129.9, 127.2, 117.8,
45.8, 21.8. MS (ESI): m/z (%) 212 (M þ 1).
NMR (125 MHz, CDCl3) d (ppm): 143.9, 132.1, 129.7, 127.9,
66.1, 45.9, 21.6. MS (ESI): m/z (%) 242 (M þ 1).
1-[(4-Methylphenyl)sulfonyl]piperidine 3b
4-Methyl-N-phenylbenzenesulfonamide 3h
White solid.[31] IR (KBr): 2929, 2831, 1453, 1338, 1168, 1093,
White solid.[27] 1H NMR (500 MHz, CDCl3) d (ppm):
7.93–7.55 (m, 3H), 7.44–6.88 (m, 7H), 2.31 (s, 3H). 13C NMR
(125 MHz, CDCl3) d (ppm): 143.8, 136.8, 136.1, 129.6, 129.2,
127.3, 125.0, 121.3, 21.5. MS (ESI): m/z (%) 248 (M þ 1).
1
932, 813, 725, 550 cmꢁ1. H NMR (500 MHz, CDCl3) d (ppm):
7.61 (d, J¼ 8.2 Hz, 2H), 7.31 (d, J¼ 8.2 Hz, 2H), 2.93 (t,
J¼ 5.5 Hz, 4H), 2.41 (s, 3H), 1.66–1.53 (m, 4H), 1.41–1.34 (m,
2H). 13C NMR (125 MHz, CDCl3) d (ppm): 143.2, 133.0, 129.4,
127.4, 46.8, 25.0, 23.3, 21.2. MS (ESI): m/z (%) 240 (M þ 1).
4-(Phenylsulfonyl)morpholine 3i
White solid.[29] IR (KBr): 2988, 1459, 1347, 1260, 1168,
1-[(4-Methylphenyl)sulfonyl]pyrrolidine 3c
1
1109, 949, 746, 693, 532 cmꢁ1. H NMR (500 MHz, CDCl3)
White solid.[27] IR (KBr): 2983, 1466, 1331, 1154, 816, 695,
d (ppm): 7.79–7.72 (m, 2H), 7.66–7.62 (m, 1H), 7.60–7.52
(m, 2H), 3.73 (t, J ¼ 4.8 Hz, 4H), 3.00 (t, J ¼ 4.8 Hz, 4H). 13C
NMR (125 MHz, CDCl3) d (ppm): 135.0, 133.0, 129.1, 127.9,
66.0, 45.8. MS (ESI): m/z (%) 228 (M þ 1).
549 cmꢁ1 1H NMR (500 MHz, CDCl3) d (ppm): 7.70 (d,
.
J ¼ 8.2 Hz, 2H), 7.31 (d, J ¼ 8.1 Hz, 2H), 3.20 (t, J ¼ 6.8 Hz,
4H), 2.42(s, 3H), 1.76–1.70 (m, 4H). 13C NMR (125 MHz,
CDCl3) d (ppm): 143.5, 134.0, 129.8, 127.9, 48.1, 25.5, 21.7.
MS (ESI): m/z (%) 248 (M þ 23).
N,N-Diethylbenzenesulfonamide 3j
Colorless viscous oil.[27] IR (KBr): 2988, 1449, 1333, 1157,
N,N-Diethyl-4-methylbenzenesulfonamide 3d
1020, 732, 692, 579 cmꢁ1 1H NMR (500 MHz, CDCl3) d
.
Pale yellow solid.[30] IR (KBr): 2978, 2930, 1464, 1330, 1154,
(ppm): 7.82–7.75 (m, 2H), 7.57–7.51 (m, 1H), 7.48 (t,
J ¼ 7.5 Hz, 2H), 3.23 (q, J ¼ 7.2 Hz, 4H), 1.11 (t, J ¼ 7.2 Hz,
6H). 13C NMR (125 MHz, CDCl3) d (ppm): 140.3, 132.2,
129.0, 126.8, 42.1, 14.0. MS (ESI): m/z (%) 214 (M þ 1).
1
815, 697, 548 cmꢁ1. H NMR (500 MHz, CDCl3) d (ppm):
7.68 (d, J ¼ 8.3 Hz, 2H), 7.29 (d, J ¼ 8.2 Hz, 2H), 3.23 (t,
J ¼ 7.2 Hz, 4H), 2.40 (s, 3 H), 1.12 (t, J ¼ 7.2 Hz, 6H). 13C
NMR (125 MHz, CDCl3) d (ppm): 142.9, 137.5, 129.5, 127.2,
42.0, 21.5, 14.0. MS (ESI): m/z (%) 228 (M þ 1).
N-Benzylbenzenesulfonamide 3k
White solid.[29] IR (KBr): 3334, 1328, 1162, 1098, 1061, 750,
N-Benzyl-4-methylbenzenesulfonamide 3e
688 cmꢁ1 1H NMR (500 MHz, CDCl3) d (ppm): 7.86 (d,
.
White solid.[30] IR (KBr): 3270, 1456, 1325, 1168, 1066, 875,
J ¼ 7.2 Hz, 2H), 7.59–7.52 (m, 1H), 7.50–7.43 (m, 2H),
7.27–7.20 (m, 3H), 7.20–7.16 (m, 2H), 5.43 (t, J ¼ 6.2 Hz,
1H), 4.12 (d, J ¼ 6.3 Hz, 2H). 13C NMR (125 MHz, CDCl3) d
(ppm): 139.9, 136.2, 132.6, 129.0, 128.5, 127.8, 127.6, 126.8,
47.0. MS (ESI): m/z (%) 265 (M þ 17).
1
746, 684, 552 cmꢁ1. H NMR (500 MHz, CDCl3) d (ppm):
7.76 (d, J ¼ 8.3 Hz, 2H), 7.33–7.23 (m, 5H), 7.24–7.20 (m,
2H), 4.95 (d, J ¼ 5.3 Hz, 1H), 4.12 (d, J ¼ 6.2 Hz, 2H), 2.46
(s, 3H). 13C NMR (125 MHz, CDCl3) d (ppm): 143.5, 136.8,
136.2, 129.7, 128.6, 127.9, 127.8, 127.4, 47.2, 21.6. MS (ESI):
m/z (%) 279 (M þ 17).
N-Cyclopentylbenzenesulfonamide 3l
Pale yellow solid.[26] IR (KBr): 3234, 2978, 1448, 1319, 1152,
N-Cyclopentyl-4-methylbenzenesulfonamide 3f
1
1092, 722, 687, 592, 555 cmꢁ1. H NMR (500 MHz, CDCl3) d
Pale yellow solid.[30] IR (KBr): 3255, 2966, 2868, 1326, 1159,
(ppm): 7.93–7.87 (m, 2H), 7.61–7.54 (m, 1H), 7.54–7.48 (m,
2H), 5.08 (d, J¼ 7.2 Hz, 1H), 3.59 (dd, J¼ 13.8, 6.8 Hz, 1H),
1.80–1.70 (m, 2H), 1.64–1.56 (m, 2H), 1.50–1.28 (m, 4H). 13C
NMR (125 MHz, CDCl3) d (ppm): 140.9, 132.4, 129.2, 127.0,
55.1, 33.3, 23.2. MS (ESI): m/z (%) 226 (M þ 1).
1090, 813, 688, 566 cmꢁ1 1H NMR (500 MHz, CDCl3) d
.
(ppm): 7.78 (d, J ¼ 8.2 Hz, 2H), 7.29 (d, J ¼ 8.0 Hz, 2H), 5.28
(d, J ¼ 7.2 Hz, 1H), 3.54 (dd, J ¼ 13.6, 6.8 Hz, 1H), 2.42 (s,
3H), 1.76–1.69 (m, 2H), 1.62–1.55 (m, 2H), 1.47–1.30 (m,
4H). 13C NMR (125 MHz, CDCl3) d (ppm): 143.0, 137.8,
129.6, 127.1, 55.0, 33.2, 23.0, 21.5. MS (ESI): m/z (%)
240 (M þ 1).
References
[1] Varvoglis, A. Chemical Transformations Induced by
Hypervalent Iodine Reagents. Tetrahedron 1997, 53, 1179–1255.
N-Allyl-4-methylbenzenesulfonamide 3g
White solid.[27] 1H NMR (500 MHz, CDCl3) d (ppm): 7.76
(d, J ¼ 7.8 Hz, 2H), 7.32 (d, J ¼ 7.8 Hz, 2H), 5.73 (ddt,
[2] Stang, P. J.; Zhdankin, V. V. Organic Polyvalent Iodine Compounds.