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P. C. Bulman Page et al.
Letter
Synlett
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UHP (2 mmol) was dissolved in CH2Cl2 (2 mL), and the solution
was stirred at r.t. A solution of Ph2Se2 (1 mol%) and sulfide (2
mmol) in CH2Cl2 (2 mL) was added to the UHP solution. The
mixture was stirred at r.t. for 24 h or until complete conversion
to sulfoxide was observed by TLC. Extraction was carried out
with CH2Cl2 (3 × 5 mL), after the addition of H2O (5 mL), and the
combined organic solutions were washed with brine (50 mL),
dried (MgSO4), filtered, and the solvents removed under
reduced pressure. Sulfoxide products were purified where nec-
essary by column chromatography.
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Sulfoxide from Thiochroman-4-one
Yellow oil. FTIR: νmax = 1694, 1585, 1325, 1282, 1237, 1182,
1120, 1080, 1039, 854 cm–1 1H NMR (400 MHz, CDCl3): δ =
.
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2.86–2.97 (1 H, m), 3.43–3.56 (3 H, m), 7.65–7.68 (1 H, m),
7.75–7.79 (1 H, m), 7.87 (1 H, dd, J = 8.1, 7.6 Hz), 8.14 (1 H, dd, J
= 8.0, 7.6 Hz) ppm. 13C NMR (100 MHz, CDCl3): δ = 30.3, 46.6,
128.5, 128.9, 132.1, 134.6, 145.5, 192.1 ppm.
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Sulfoxide from 4-Fluorothioanisole
Yellow oil. FTIR: νmax = 3096, 3062, 2996, 1655, 1641, 1046
(S=O), 958, 834 (C–F) cm–1. 1H NMR (400 MHz, CDCl3): δ = 2.73
(3 H, s), 7.21–7.26 (2 H, m), 7.66–7.69 (2 H, m) ppm. 13C NMR
(100 MHz, CDCl3): δ = 44.0, 117.0, 125.5, 130.1, 141.2 ppm.
Sulfoxide from 2-Chloroethyl Ethyl Sulfide
Yellow oil. FTIR: νmax = 1653, 1455, 1301, 1127, 1020, 864 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 1.37 (3 H, t, J = 7.6 Hz), 2.76–2.86
(2 H, m), 3.04–3.08 (2 H, m), 3.89–4.00 (2 H, m) ppm. 13C NMR
(100 MHz, CDCl3): δ = 6.7, 37.0, 46.0, 54.0 ppm.
Sulfoxide from Furfuryl Methyl Sulfide
Yellow oil. FTIR: νmax = 2972, 2916, 1423, 1033, 933, 744 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.52 (3 H, s), 4.06 (2 H, q, J =
13.92 Hz), 6.40 (2 H, m), 7.39 (1 H, dd, J = 2.0 Hz) ppm. 13C NMR
(100 MHz, CDCl3): δ = 37.9, 52.2, 111.2, 143.5, 143.9 ppm.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, 80–82