PAPER
CAN Mediated Reaction: Synthesis of Vinyl Sulfones, -Iodovinyl Sulfones and Acetylenic Sulfones
2263
(d, 1 H, ArH, J = 8.0 Hz), 6.92 (d, 1 H, olefinic, J = 15.1 Hz), 2.44
(s, 3 H, CH3).
IR (KBr): 3036, 2982, 2928, 1600, 1445, 1303, 1155, 1108, 1081,
966, 818, 744, 663, cm–1.
13C NMR: = 144.26, 138.92, 137.92, 133.72, 131.34, 130.18,
130.01, 129.73, 128.85, 127.89, 127.31, 126.50, 125.63, 125.28,
123.16, 21.68.
1H NMR: = 7.80–7.74 (m, 3 H, ArH), 7.33–7.27 (m, 4 H, ArH,
CH=CH), 7.20–7.15 (m, 2 H, ArH), 2.44 (s, 3 H, CH3), 2.37 (s, 3 H,
CH3), 2.09 (s, 3 H, CH3).
Anal. Calcd for C19H16O2S: C, 74.00; H, 5.23; S, 10.40. Found: C,
74.36; H, 5.88; S, 10.54.
13C NMR: = 143.92, 139.42, 137.01, 136.51, 131.11, 129.76,
129.71, 129.38, 128.28, 127.95, 21.64, 21.42, 13.26.
1-(4 -Methylphenylsulfonyl)-2-(4 -acetoxyphenyl)ethene (2j)
1-Phenylsulfonyl-1-methyl-2-(4 -methylphenyl)ethane (3b)21a,22
Mp 127–129 °C.
Mp 89–90 °C.
IR (KBr): 3049, 1769, 1613, 1506, 1371, 1317, 1209, 1142, 1088,
987, 919, 804, 589 cm–1.
1H NMR: = 7.80 (d, 2 H, ArH, J = 8.1 Hz), 7.61 (d, 1 H, olefinic,
J = 15.4 Hz), 7.48 (d, 2 H, ArH, J = 8.5 Hz), 7.33 (d, 2 H, ArH,
J = 8.0 Hz), 7.11 (d, 2 H, ArH, J = 8.5 Hz), 6.78 (d, 1 H, olefinic,
J = 15.4 Hz), 2.44 (s, 3 H, OCOCH3), 2.29 (s, 3 H, CH3).
1-(4 -Methylphenylsulfonyl)-oct-1-ene (4a)19b,c
Colorless viscous liquid.
1-(Phenylsulfonyl)-oct-1-ene (4b)20
Colorless viscous liquid.
13C NMR: = 168.50, 152.61, 144.14, 140.60, 137.83, 130.07,
129.86, 129.60, 127.88, 127.70, 122.26, 21.57, 21.00.
1-(4 -Methylphenylsulfonyl)-2-iodocyclohexane (5a) and 1-(4 -
Methylphenylsulfonyl)-cyclohex-1-ene (5b)19a,b,21b
5a Colorless viscous liquid.
Anal. Calcd for C17H16O4S: C, 64.54; H, 5.10; S, 10.14. Found: C,
64.43; H, 5.53; S, 10.22.
5b Colorless crystalline solid, recrystallized, mp 79–80 °C.
1-Phenylsulfonyl-2-phenylethene (2b)19c,21
Mp 70–71 °C.
2-(4 -Methylphenylsulfonyl)-1-phenyl-cyclohex-1-ene (6a) and
2-(4 -Methylphenylsulfonyl)-1-hydroxyphenylcyclohexane (6b)
6a
1-Phenylsulfonyl-2-(4 -methylphenyl)ethene (2d)20
Mp 127–130 °C.
Mp 132–135 °C.
IR (KBr): 3029, 2948, 2908, 1607, 1452, 1297, 1142, 1088, 912,
771, 730 cm–-1.
1H NMR: = 7.50-7.48 (m, 2 H, ArH), 7.38–7.16 (m, 2 H, ArH),
7.04–6.95 (m, 5 H, ArH), 6.21–6.20 (m, 1 H, olefinic), 4.32 (m, 1
H, CHSO2), 2.82–2.77 (m, 1 H, CH2), 2.35–2.14 (m, 3 H, CH2), 2.30
(s, 3 H, CH3), 1.92–1.89 (m, 1 H, CH2), 1.87–1.76 (m, 1 H, CH2).
1-Phenylsulfonyl-2-(4 -chlorophenyl)ethene (2f)20,21b
Mp 129–130 °C
1-Phenylsulfonyl-2-(3 -nitrophenyl)ethene (2i)21b
Mp 126–128 °C.
13C NMR : 143.48, 137.17, 135.07, 131.24, 129.05, 128.70,
128.04, 127.19, 126.55, 126.39, 62.78, 25.57, 23.49, 21.50, 17.45.
1-Phenylsulfonyl-2-(2-naphthyl)ethene (2m)
Mp 99–101 °C.
6b
IR (KBr): 3052, 1611, 1595, 1479, 1448, 1306, 1289, 1142, 1067,
964, 846 cm–1.
Mp157–159 °C.
IR (KBr): 3494, 2942, 2867, 1607, 1449, 1310, 1290, 1135, 1081,
973, 746 cm–1.
1H NMR: = 7.63–7.61 (m, 2 H, ArH), 7.48 (d, 2 H, ArH, J = 8.1
Hz), 7.25–7.23 (m, 3 H, ArH), 7.19 (d, 2 H, ArH, J = 8.1 Hz), 4.33
(br s, 1 H, OH, exchangeable with D2O), 3.60–3.55 (m, 1 H,
CHSO2), 2.41 (s, 3 H, CH3), 2.33–1.35 (m, 8 H, CH2).
1H NMR: = 7.87–7.84 (m, 2 H, ArH), 7.73–7.64 (m, 4 H, ArH),
7.63 (d, 1 H, olefinic, J = 15.2 Hz), 7.45–7.34 (m, 6 H, ArH), 6.84
(d, 1 H, olefinic, J = 15.3 Hz).
13C NMR: = 142.29, 140.86, 134.32, 133.14, 132.93, 130.74,
129.65, 129.18, 128.75, 128.53, 127.66, 127.60, 127.54, 127.35,
126.80, 123.33.
13C NMR: = 144.03, 143.76, 137.10, 129.51, 128.30, 127.84,
127.49, 127.12, 74.98, 73.49, 25.30, 24.38, 21.58, 21.33.
Anal. Calcd for C18H14O2S: C, 73.44; H, 4.79; S, 10.89. Found: C,
73.71; H, 4.88; S, 10.83.
Anal. Calcd for C19H22O3S: C, 69.06; H, 6.71; S, 9.70. Found: C,
69.03; H, 7.06; S, 9.65.
1-Phenylsulfonyl-2-(4 -acetoxyphenyl)ethene (2k)
Mp 126–127 °C.
2-(Phenylsulfonyl)-1-phenyl-1-cyclohexene (6c) and 2-(Phenyl-
sulfonyl)-1-hydroxy-1-phenylcyclohexane (6d)
6c
IR (KBr): 3049, 1755, 1613, 1506, 1445, 1378, 1317, 1135, 1088,
1013, 973, 818, 690 cm–1.
1H NMR: = 7.94–7.92 (m, 2 H, ArH), 7.68–7.56 (m, 3 H, ArH),
7.57 (d, 1 H, olefinic, J = 15.1 Hz), 7.50 (d, 2 H, ArH, J = 8.5 Hz),
7.12 (d, 2 H, ArH, J = 8.5 Hz), 6.79 (d, 1 H, olefinic, J = 15.3 Hz),
2.30 (s, 3 H, OCOCH3).
Mp 86–89 °C.
IR (KBr) 3063, 2948, 1445, 1297, 1135, 1081, 724, 697, 622 cm–1.
1H NMR: 7.50–7.47 (m, 2 H, ArH), 7.38–7.33 (m, 1 H, ArH),
7.21–7.16 (m, 2 H, ArH), 7.02–7.00 (m, 5 H, ArH), 6.22–6.21 (m,
1 H, olefinic), 4.36 (m, 1 H, CHSO2), 2.85–2.80 (m, 1 H, CH2),
2.42–2.10 (m, 3 H, CH2), 1.95–1.89 (m, 1 H, CH2), 1.83–1.73 (m, 1
H, CH2).
13C NMR: = 140.84, 140.21, 134.98, 132.67, 131.11, 128.50,
128.34, 128.02, 126.80, 126.30, 62.72, 25.47, 23.36, 17.43.
13C NMR: = 168.53, 152.71, 141.19, 133.24, 129.66, 129.23,
127.62, 127.52, 122.29, 20.99.
1-(4 -Methylphenylsulfonyl)-1-methyl-2-(4 -methylphe-
nyl)ethene(3a)
Mp 113–115 °C.
Synthesis 2002, No. 15, 2259–2265 ISSN 0039-7881 © Thieme Stuttgart · New York