J IRAN CHEM SOC
General procedure
δ = 22.6, 41.4); anal. calcd for C6H14S2: C, 47.95; H, 9.39;
S, 42.66. Found: C, 48.04; H, 9.44; S, 42.52 %.
A mixture of an alkyl halide (2 mmol), thiourea (2.5 mmol),
Et3N (3.5 mmol) and CCl4 (2 mmol) in wet glycerol (2 mL
glycerol + 0.1 mL H2O) was stirred magnetically at 50 °C
for 12–24 h. Then H2O (1 mL) was added to the reac-
tion mixture and the reaction was extracted with EtOAc
(3 × 2 mL). The organic layers were decanted, combined,
dried over Na2SO4, and concentrated to yield the crude
disulfide, which was further purified by silica gel chroma-
tography using low-boiling petroleum ether as eluent to
provide the desired disulfides in good to excellent yields
Conclusion
In conclusion, we have developed a one-pot and odorless
preparation of disulfides from alkyl halides using thiourea
as a cheap and available sulfur surrogate and CCl4 in the
presence of Et3N under mild conditions. Various primary
and secondary, allylic and benzylic halides can be effec-
tively used to produce the corresponding symmetrical
disulfides in good to excellent yields.
Bis(4-methylbenzyl) disulfide (2b) colorless oil; 1HNMR
(250 MHz, CDCl3): δ = 2.21 (s, 6H), 3.71 (s, 4H), 7.05–
7.33 (m, 8H); 13CNMR (62.5 MHz, CDCl3): δ = 137.6,
134.8, 129.8, 129.1, 43.1, 21.4; anal. calcd for C16H18S2:
C, 70.02; H, 6.61; S, 23.37 %. Found: C, 70.16; H, 6.52; S,
23.32 %.
Acknowledgments We gratefully acknowledge the support of this
study by the Persian Gulf University and Shiraz University Research
Council.
References
Bis(2-methyl-2-propenyl) disulfide (2e) colorless oil;
1HNMR (250 MHz, CDCl3): δ 1.80 (s, 6H), 3.27 (s,
4H), 4.77–4.86 (m, 4H); 13CNMR (62.5 MHz, CDCl3):
δ = 141.0, 115.1, 46.6, 20.7; anal. calcd for C8H14S2: C,
55.12; H, 8.09; S, 36.79 %. Found: C, 55.21; H, 7.96; S,
36.83 %.
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Octyl disulfide (2 h) colorless oil; HNMR (250 MHz,
CDCl3): δ = 0.83–0.89 (m, 6H), 1.27–1.36 (m, 20H),
1.53–1.68 (m, 4H), 2.64 (t, J = 7.3 Hz, 4H); 13CNMR
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1
Decyl disulfide (2 k) colorless oil; HNMR (250 MHz,
CDCl3): δ = 0.80–0.85 (m, 6H), 1.21–1.35 (m, 28H), 1.59–
1.73 (m, 4H), 2.64 (t, J = 7.3 Hz, 4H); 13CNMR (62.5 MHz,
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22.8, 14.2; anal. calcd for C20H42S2: C, 69.29; H, 12.21; S,
18.50 %. Found: C, 69.41; H, 12.13; S, 18.46 %.
Cyclohexyl disulfide (2n) colorless oil; 1HNMR
(250 MHz, CDCl3): δ 1.17–1.31 (m, 10H), 1.52–1.64 (m,
2H), 1.70–1.82 (m, 4H), 1.99–2.06 (m, 4H), 2.64–2.73 (m,
2H); 13CNMR (62.5 MHz, CDCl3): δ = 50.1, 32.7, 26.1,
25.7; anal. calcd for C12H22S2: C, 62.55; H, 9.62; S, 27.83.
Found: C, 62.39; H, 9.75; S, 27.86 %.
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n-Propyl disulfide (2f) colorless oil; 1HNMR
(250 MHz, CDCl3): δ = 0.99(t, J = 7.4 Hz, 6H), 1.71
(sext, J = 7.4 Hz, 4H), 2.66 (t. J = 7.4 Hz, 4H); 13CNMR
(62.5 MHz, CDCl3): δ = 13.1, 22.5, 41.2; anal. calcd for
C6H14S2: C, 47.95; H, 9.39; S, 42.66. Found: C, 47.82; H,
9.50; S, 42.68 %.
iso-Propyl disulfide (2 k) colorless oil: 1HNMR
(250 MHz, CDCl3): δ = 1.30 (d, J = 6.9 Hz, 12H), 2.97
(sept, J = 6.9 Hz, 2H); 13CNMR (62.5 MHz, CDCl3):
1 3