b-Phenyl-chalcogenyl Allyl Sulfones
2609
(s, 2H), 2.02 (s, 3H), 1.81 (s, 3H); 13C NMR (100 MHz, CDCl3): d ¼ 150.3,
139.2, 133.7, 131.3, 130.8, 129.2, 129.0, 128.6, 126.8, 111.4, 62.0, 26.4, 21.8;
IR nmax (neat): 2914, 1307, 1139, 743 cm21; MS (EI, 70 eV): m/z (%) ¼ 183
(100), 366 (18) [Mþ]. Anal. calcd. for C17H18O2SSe: C, 55.89; H, 4.97; found:
C, 55.94; H, 5.01.
3i: Solid, mp 76–78 8C. 1H NMR (400 MHz, CDCl3): d ¼ 7.83
(d, J ¼ 9.32 Hz, 2H), 7.63 (t, 1H), 7.49 (t, 2H), 7.44 (m, 2H), 7.26 (m, 5H),
7.08 (d, J ¼ 8.36 Hz, 2H), 6.99 (s, 1H), 4.26 (s, 2H); 13C NMR (100 MHz,
CDCl3): d ¼ 139.8, 139.1, 134.4, 133.9, 133.8, 133.7, 129.4, 129.3, 129.2,
129.0, 128.6, 128.4, 128.3, 122.8, 59.7; IR nmax (neat): 3061, 1316, 1140,
742 cm21; MS (EI, 70 eV): m/z (%) ¼ 115 (100), 448 (14) [Mþ]. Anal.
calcd. for C21H17ClO2SSe: C, 56.32; H, 3.83; found: C, 56.24; H, 3.91.
3j: Solid, mp 107–109 8C. 1H NMR (400 MHz, CDCl3): d ¼ 7.83
(d, J ¼ 8.40 Hz, 2H), 7.67 (t, 1H), 7.55 (t, 2H), 7.30 (m, 9H), 6.97 (s, 1H),
3.97 (s, 2H); 13C NMR (100 MHz, CDCl3): d ¼ 140.3, 138.7, 134.5, 133.7,
133.6, 133.4, 130.1, 129.4, 129.3, 129.0, 128.7, 128.5, 128.4, 121.9, 55.7;
IR nmax (neat): 3060, 1314, 1138, 744 cm21; MS (EI, 70 eV): m/z
(%) ¼ 115 (100), 448 (19) [Mþ]. Anal. calcd. for C21H17ClO2SSe:
C, 56.32; H, 3.83; found: C, 56.27; H, 3.93.
3k: Solid, mp 67–69 8C. 1H NMR (400 MHz, CDCl3): d ¼ 7.87
(d, J ¼ 7.40 Hz, 2H), 7.66 (t, 1H), 7.54 (t, 2H), 7.31 (m, 2H), 7.25 (m, 3H),
6.28 (t, 1H), 4.08 (s, 2H), 1.99 (m, 2H), 1.27 (m, 4H), 0.91 (t, 3H); 13C NMR
(100 MHz, CDCl3): d ¼ 147.7, 138.9, 133.8, 132.8, 129.7, 129.2, 129.0,
128.7, 127.5, 116.5, 59.6, 30.7, 30.1, 22.2, 13.8; IR nmax (neat): 2955, 1309,
1148, 746 cm21; MS (EI, 70 eV): m/z (%) ¼ 252 (100), 394 (11) [Mþ].
Anal. calcd. for C19H22O2SSe: C, 58.01; H, 5.64; found: C, 58.11; H, 5.56.
3l: Solid, mp 73–75 8C. 1H NMR (400 MHz, CDCl3): d ¼ 7.87
(d, J ¼ 7.41 Hz, 2H), 7.65 (t, 1H), 7.53 (t, 2H), 7.27 (m, 5H), 6.07 (t, 1H),
3.93 (s, 2H), 2.27 (m, 2H), 1.30 (m, 4H), 0.89 (t, 3H); 13C NMR (100 MHz,
CDCl3): d ¼ 146.1, 138.5, 133.7, 132.8, 129.3, 129.1, 128.9, 128.8, 127.5,
118.4, 64.0, 32.2, 30.8, 22.2, 13.8; IR nmax (neat): 2961, 1307, 1141,
741 cm21; MS (EI, 70 eV): m/z (%) ¼ 95 (100), 394 (11) [Mþ]. Anal.
calcd. for C19H22O2SSe: C, 58.01; H, 5.64; found: C, 58.07; H, 5.49.
3m: Solid, mp 96–98 8C. 1H NMR (400 MHz, CDCl3): d ¼ 7.68
(d, J ¼ 7.32 Hz, 2H), 7.63 (t, 1H), 7.47 (t, 2H), 7.35 (m, 2H), 7.26 (m, 5H),
6.94 (d, J ¼ 8.40 Hz, 2H), 4.10 (s, 2H), 2.25 (s, 3H); 13C NMR (100 MHz,
CDCl3): d ¼ 151.5, 139.8, 139.6, 133.5, 133.4, 132.0, 130.3, 129.4, 129.0,
128.9, 128.7, 128.5, 127.3, 116.6, 62.0, 27.1; IR nmax (neat): 3060, 2920,
1312, 1141, 739 cm21; MS (EI, 70 eV): m/z (%) ¼ 129 (100), 462 (29) [Mþ].
Anal. calcd. for C22H19ClO2SSe: C, 57.21; H, 4.15; found: C, 57.29; H, 4.08.