G. Perin et al.
1H, O-CH), 4.50 (dd, J = 8.8 and 8.0 Hz, 1H, O-CH2), 4.23 (dd, J = 8.8 and
6.4 Hz, 1H, O-CH2), 3.32 (dd, J = 14.1 and 4.4 Hz, 1H, S-CH2), 3.02 (dd, J = 14.1
and 8.7 Hz, 1H, S-CH2), 2.33 (s, 3H, Ar-CH3). 13C NMR (CDCl3, 125 MHz)
d = 154.4, 138.1, 131.7, 130.2, 129.3, 74.7, 68.5, 37.5, 21.0. MS (EI): m/z (%
relative intensity) = 224 (62.9), 137 (100.0), 122 (27.0), 45 (40.0). HRMS:
Calculated mass for C11H12O3S: [M ? H]? 225.0585, found: 225.0564.
4-(2-Chlorophenylthio)methyl-1,3-dioxolan-2-one (3f)
1
Yield: 0.107 g (88 %); white solid; m.p. 72–73 °C. H NMR (CDCl3, 500 MHz)
d = 7.48–7.46 (m, 1H, Ar-H), 7.44–7.42 (m, 1H, Ar-H), 7.28–7.23 (m, 2H, Ar-H),
4.80–4.75 (m, 1H, O-CH), 4.57 (dd, J = 8.9 and 8.0 Hz, 1H, O-CH2), 4.31 (dd,
J = 8.9 and 6.3 Hz, 1H, O-CH2), 3.40 (dd, J = 14.1 and 4.5 Hz, 1H, S-CH2), 3.13
(dd, J = 14.1 and 8.4 Hz, 1H, S-CH2). 13C NMR (CDCl3, 125 MHz) d = 154.3,
136.0, 132.1, 132.0, 130.3, 129.0, 127.6, 74.5, 68.5, 36.0. MS (EI): m/z (% relative
intensity) = 244 (50.5), 157 (100.0), 45 (46.2). HRMS: Calculated mass for
C10H9ClO3S: [M ? H]? 245.0039, found: 245.0019.
4-(2-Tolylthio)methyl-1,3-dioxolan-2-one (3g)
1
Yield: 0.095 g (85 %); white solid; m.p. 43–45 °C. H NMR (CDCl3, 500 MHz)
d = 7.38–7.35 (m, 1H, Ar-H), 7.24–7.17 (m, 3H, Ar-H), 4.77–4.72 (m, 1H, O-CH),
4.52 (dd, J = 8.8 and 7.9 Hz, 1H, O-CH2), 4.27 (dd, J = 8.8 and 6.3 Hz, 1H,
O-CH2), 3.35 (dd, J = 13.9 and 4.4 Hz, 1H, S-CH2), 3.03 (dd, J = 13.9 and 8.8 Hz,
1H, S-CH2), 2.42 (s, 1H, Ar-CH3). 13C NMR (CDCl3, 125 MHz) d = 154.4, 139.4,
132.2, 130.9, 130.8, 127.8, 126.9, 74.6, 68.6, 36.2, 20.5. MS (EI): m/z (% relative
intensity) = 224 (61.6), 137 (64.5), 122 (100.0), 45 (91.0). HRMS: Calculated mass
for C11H12O3S: [M ? H]? 225.0585, found: 225.0564.
4-(2-Aminophenylthio)methyl-1,3-dioxolan-2-one (3h)
Yield: 0.073 g (65 %); pale-yellow solid; m.p. 89–91 °C. 1H NMR (CDCl3,
300 MHz) d = 7.37 (dd, J = 7.4 and 1.5 Hz, 1H, Ar-H), 7.18 (ddd, J = 8.0, 7.4,
and 1.6 Hz, 1H, Ar-H), 6.71 (td, J = 7.4 and 1.3 Hz, 1H, Ar-H), 4.75–4.65 (m, 1H,
O-CH), 4.52 (dd, J = 8.7 and 8.0 Hz, 1H, O-CH2), 4.19 (dd, J = 8.7 and 6.4 Hz,
1H, O-CH2), 3.18 (dd, J = 13.8 and 4.8 Hz, 1H, S-CH2), 2.92 (dd, J = 13.8 and
8.3 Hz, 1H, S-CH2). 13C NMR (CDCl3, 75 MHz) d = 154.5, 148.6, 136.4, 131.0,
118.9, 115.4, 114.4, 75.2, 68.7, 36.5. MS (EI): m/z (% relative intensity) = 225
(61.5), 136 (48.0), 124 (100.0), 94 (33.3). HRMS: Calculated mass for C10H11-
NO3S: [M ? H]? 226.0538, found: 226.0523.
4-(Benzo[d]thiazol-2-ylthio)methyl-1,3-dioxolan-2-one (3i)
1
Yield: 0.073 g (55 %); yellow solid; m.p. 88–90 °C. H NMR (CDCl3, 300 MHz)
d = 7.88–7.84 (m, 1H, Ar-H), 7.79–7.76 (m, 1H, Ar-H), 7.47–7.44 (m, 1H, Ar-H),
7.36–7.31 (m, 1H, Ar-H), 5.26–5.17 (m, 1H, O-CH), 4.62 (dd, J = 9.0 and 8.1 Hz,
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