Journal of Sulfur Chemistry 193
1-Indanyl-(4-bromophenyl)sulfane (3d): Pale yellow liquid. 1H NMR (400 MHz, CDCl3): δ 2.14–
2.21 (m, 1H), 2.47–2.57 (m, 1H), 2.81–2.87 (m, 1H), 2.96–3.04 (m, 1H), 4.71–4.73 (dd, 1H,
J = 4.0, 7.2 Hz), 7.17–7.28(m, 6H), 7.38–7.40(d, 2H, J = 8.4 Hz). 13CNMR(100 MHz, CDCl3):
δ 30.79, 33.60, 52.20, 120.92, 124.71, 124.88, 126.55, 127.86, 131.86, 133.15, 135.16, 142.54,
143.68. EI MS: m/z (rel. abund. %) 304 (M(79Br), 99), 306 (M(81Br), 100). Anal. Calcd. for
C15H13BrS (305.23): C, 59.02; H, 4.29; S, 10.51. Found: C, 58.97; H, 4.32; S, 10.45%.
1-Indanyl-(4-tolyl)sulfane (3e): Pale yellow liquid; bp 135–136 ◦C (2 mm) (9). 1H NMR
(400 MHz, CDCl3): δ 2.15–2.22 (m, 1H), 2.33 (s, 3H), 2.44–2.53 (m, 1H), 2.79–2.86 (m, 1H),
2.96–3.04 (m, 1H), 4.67–4.70 (dd, 1H, J = 4.2, 7.4 Hz), 7.08–7.10 (d, 2H, J = 8.0 Hz), 7.17–7.21
(m, 3H), 7.26–7.30 (m, 3H). 13C NMR (100 MHz, CDCl3): δ 20.82, 30.77, 33.73, 52.64, 124.48,
124.92, 126.34, 127.50, 129.45, 132.24, 132.42, 136.92, 143.25, 143.63. EI MS: m/z (rel. abund.
%) 241.3 [M+, 100].
1-Indanyl-(benzyl)sulfane (3f): Pale yellow liquid. 1H NMR (400 MHz, CDCl3): δ 2.10–2.14 (m,
1H), 2.38–2.47 (m, 1H), 2.77–2.85 (m, 1H), 2.99–3.07 (m, 1H), 3.69–3.77 (dd, 2H, J = 13.2,
18.8 Hz), 4.20–4.23 (dd, 1H, J = 4.8, 7.2 Hz), 7.16–7.21 (m, 4H), 7.27–7.32 (m, 5H). 13C NMR
(100 MHz, CDCl3): δ 31.05, 34.10, 35.84, 49.10, 124.60, 124.82, 126.48, 126.86, 127.46, 128.43,
128.88, 138.73, 143.39, 143.61. EI MS: m/z (rel. abund. %) 241.3 [M+, 100]. Anal. Calcd. for
C16H16S (240.36): C, 79.95; H, 6.74; S, 13.34. Found: C, 79.89; H, 6.75; S, 13.29%.
1-Indanyl-(2,4-dichlorophenyl)sulfane (3g): Colorless solid; mp 79–91 ◦C. 1H NMR (400 MHz,
CDCl3): δ 2.15–2.22 (m, 1H), 2.49–2.58 (m, 1H), 2.87–2.94 (m, 1H), 3.09–3.17 (m, 1H), 4.83–
4.85 (dd, 1H, J = 3.2, 7.2 Hz), 7.17–7.27 (m, 5H), 7.30–7.32 (d, 1H, J = 8.4 Hz), 7.41–7.42 (d,
1H, J = 2.0 Hz). 13C NMR (100 MHz, CDCl3): δ 30.77, 33.50, 51.49, 124.69, 124.87, 126.56,
127.16, 128.00, 129.64, 132.93, 133.07, 134.41, 136.64, 142.00, 143.76. EI MS: m/z (rel. abund.
%) 296.2 [M, 100], 298.2 [M+, 66]. Anal. Calcd. for C15H12Cl2S (295.23): C, 61.02; H, 4.10; S,
10.86. Found: C, 61.11; H, 4.15; S, 10.69%.
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1-Indanyl-(3,5-dichlorophenyl)sulfane (3h): White solid; mp 52–53 ◦C. H NMR (400 MHz,
CDCl3):δ 2.18–2.25(m, 1H), 2.55–2.65(m, 1H), 2.88–2.95(m, 1H), 3.03–3.11(m, 1H),4.80–4.83
(dd, 1H, J = 4.0, 7.2 Hz), 7.20–7.26 (m, 6H), 7.30–7.32 (d, 1H, J = 6.8 Hz). 13C NMR (100 MHz,
CDCl3): δ 30.76, 33.75, 52.03, 124.72, 124.85, 126.55, 126.66, 128.10, 128.50, 135.09, 140.15,
141.80, 143.64. EI MS: m/z (rel. abund. %) 296.2 [M+, 100], 298.2 [M+, 66]. Anal. Calcd. for
C15H12Cl2S (295.23): C, 61.02; H, 4.10; S, 10.86. Found: C, 61.10; H, 4.12; S, 10.81%.
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1-Indanyl-(3,4-dichlorophenyl)sulfane (3i): White solid; mp 66–68 ◦C. H NMR (400 MHz,
CDCl3): δ 2.14–2.22 (m, 1H), 2.50–2.60 (m, 1H), 2.84–2.91 (m, 1H), 2.98–3.06 (m,
1H), 4.74–4.77 (dd, 1H, J = 4.0, 7.2 Hz), 7.16–7.29 (m, 5H), 7.32–7.34 (d, 1H, J =
8.4 Hz), 7.43–7.44 (d, 1H, J = 2.0 Hz ). 13C NMR (100 MHz, CDCl3): δ 30.77, 33.60,
52.23, 124.79, 124.87, 126.64, 128.06, 130.42, 131.00, 132.67, 132.76, 136.38, 142.05,
143.70. EI MS: m/z (rel. abund. %) 296.2 [M, 100], 298.2 [M+, 66]. Anal. Calcd.
for C15H12Cl2S (295.23): C, 61.02; H, 4.10; S, 10.86. Found: C, 60.98; H, 4.08; S,
10.91%.
1-Indanyl-(2,4-dimethylphenyl)sulfane (3j): Pale yellow liquid. 1H NMR (400 MHz, CDCl3): δ
2.13–2.20 (m, 1H), 2.31 (s, 3H), 2.32 (s, 3H), 2.42–2.51 (m, 1H), 2.82–2.89 (m, 1H), 3.06–
3.14 (m, 1H), 4.66–4.69 (dd, 1H, J = 3.2, 7.2 Hz), 6.95–6.98 (dd, 1H, J = 0.8, 8.0 Hz), 7.02
(s, 1H), 7.13–7.23 (m, 4H), 7.31–7.33 (d, 1H, J = 7.6 Hz ). 13C NMR (100 MHz, CDCl3):
δ 20.40, 20.74, 30.81, 33.67, 52.17, 124.50, 124.82, 126.29, 127.01, 127.52, 131.06, 131.79,
132.76, 136.95, 139.93, 143.35, 143.66. EI MS: m/z (rel. abund. %) 255.2 [M+, 100]. Anal.
Calcd. for C17H18S (254.39): C, 80.26; H, 7.13; S, 12.60. Found: C, 80.31; H, 7.23; S,
12.51%.