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Green Chemistry
Page 6 of 8
DOI: 10.1039/C7GC03864J
ARTICLE
Journal Name
2-(Methylsulfinyl)methyl benzoate (3q):[20] The crude product was
purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 1:1) to give 3q as white solid (20.3 mg, 34%);
1H NMR (400 MHz, CDCl3): δ = 8.32 (d, J = 7.9 Hz, 1H), 8.10 (d, J = 7.7
Hz, 1H), 7.84 (t, J = 7.6 Hz, 1H), 7.59 (t, J = 7.6 Hz 1H), 3.96 ( s, 3H),
2.85 (s, 3H); 13C NMR (100 MHz, CDCl3): δ = 165.6, 150.2, 133.9,
130.6, 130.1, 126.3, 124.0, 52.5, 43.9.
Acknowledgements
We are grateful to the National Natural Science Foundation of
China (Grant Nos. 21672074 and 21372089) for financial
support.
Notes and references
4-(Trifluoromethyl)phenyl methylsulfoxide (3r):[22] The crude
product was purified by column chromatography on silica gel
(petroleum ether/ethyl acetate = 1:1) to give 3r as white oil (26.2
mg, 42%); 1H NMR (400 MHz, CDCl3): δ = 7.85-7.69 (m, 4H), 2.73 (s,
3H); 13C NMR (100MHz, CDCl3): δ = 150.0, 133.2 (q, J = 31.3 Hz),
126.3 (q, J = 3.6 Hz) , 124.0, 123.5(q, J = 274.0 Hz) , 43.8.
1
2
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2-(Methylsulfinyl)naphthalene (3s):[18] The crude product was
purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 2:1) to give 3s as white solid (43.3 mg, 76%);
1H NMR (400 MHz, CDCl3) δ = 8.17 (s, 1H), 7.94-7.86 (m, 3H), 7.57-
7.53 (m, 3H), 2.75 (s, 3H); 13C NMR (100 MHz, CDCl3): δ = 142.7,
134.3, 132.8, 129.5, 128.4, 127.9, 127.7, 127.3, 123.9, 119.4, 43.7.
3
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2-(Methylsulfinyl)ethylbenzene (3u):[23] The crude product was
purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 2:1) to give 3u as white solid (41.3 mg, 82%);
1H NMR (400 MHz, CDCl3) δ = 7.34-7.32 (m, 2H), 7.30-7.25 (m, 3H),
3.13-3.09 (m, 2H), 2.96 (dd, J = 8.0, 17.2 Hz, 2H), 2.58 (s, 3H); 13C
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28.7.
5
6
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2H), 1.45-1.40 (m, 2H), 1.30-1.28 (m, 4H), 0.85 (t, J = 6.8 Hz, 3H); 13
C
5
NMR (100 MHz, CDCl3): δ = 54.7, 38.5, 31.3, 28.4, 22.5, 22.4, 13.9.
8
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Cyclohexyl methyl sulfoxide (3w):[18] The crude product was
purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 3:1) to give 3w as colorless oil (29.8 mg, 68%);
1H NMR (400 MHz, CDCl3) δ = 2.52-2.44 (m, 1H), 2.48 (s,3H), 2.12-
2.09 (d, J = 12.7 Hz, 1H), 1.88-1.83 (m, 3H), 1.70-1.67 (d, J = 12.0 Hz,
1H), 1.42-1.18 (m, 5H); 13C NMR (100 MHz, CDCl3): δ = 60.8, 35.1,
26.0, 25.5, 25.3, 25.1, 24.8.
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In summary, an electrochemical synthesis of sulfoxides from
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thiophenols
/ thiols and dimethyl sulfoxide has been
developed. A series of sulfoxides were prepared by this
method. Thiophenols, primary and secondary aliphatic thiols
are suitable substrates for this transformation to afford
desired products in moderate to good yields. The reaction is
selective, mild and environmentally friendly. Further inves-
tigation to determine the mechanism of this reaction and to
expand its scope is underway in our laboratory.
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Conflicts of interest
There are no conflicts to declare.
6 | J. Name., 2012, 00, 1-3
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