4
Tetrahedron
(
b) Tyson EL, Ament MS, Yoon TP. J Org Chem. 2013; 78:
2 4
combined organic phase was dried over anhydrous Na SO ,
2
046.
filtered and evaporated under reduced pressure. The
resulting crude product was purified by silica gel
chromatography using a mixture of hexane/ethyl acetate (4:1)
as eluent to afford an analytically pure sample of product 3. All
the compounds 3 are known and were characterized by
comparison of their spectral data with those reported in the
1
1
1
1
1
0. Keylor MH, Park JE, Wallentin C-J, Stephenson CRJ.
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17-19
literature.
Characterization data of representative
compounds 3 are given below :
19
1
Compound 3a:
3
H NMR (400 MHz, CDCl ) δ: 7.66-7.62 (m,
4. (a) Yu B, Guo CX, Zhong CL, Diao ZF, He LN. Tetrahedron
Lett. 2014; 55: 1818;
2H), 7.57-7.46 (m, 3H), 7.34-7.28 (m, 2H), 7.21-7.14 (m, 3H),
13
3.11-2.98 (m, 3H), 2.90-2.84 (m, 1H); C NMR (100 MHz,
CDCl ) δ: 143.6, 138.9, 131.0, 129.2, 128.7, 128.5, 126.6, 124.0,
(
b) Xia M, Chen ZC, Synth Commun. 1997; 27: 1315.
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3
1
58.2, 28.3; HRMS (EI): calc. for C14
230.0761.
Compound 3g: H NMR (400 MHz, CDCl
H
14OS 230.0765, found
(
19 1
3
) δ: 7.56 (d, J = 8.5
(
(
1
Hz, 2H), 7.50 (d, J = 8.5 Hz, 2H), 7.30 (t, J = 7.3 Hz, 2H), 7.25
(t, J = 7.3 Hz, 1H), 7.16 (d, J = 7.3 Hz, 2H), 3.12-3.01 (m, 3H),
1
3
2.90-2.86 (m, 1H); C NMR (100 MHz, CDCl
137.4, 129.5, 128.7, 128.4, 126.7, 125.5, 58.3, 28.2; HRMS (EI):
calc.for C14 13ClOS 264.0376, found 264.0379.
Compound 3p: H NMR (400 MHz, CDCl
7.2 Hz, 4H), 7.21-7.15 (m, 6H), 3.09-2.98 (m, 4H), 2.91-2.88
3
) δ: 142.1, 138.5,
(
(
e) Das R. Chakraborty D, Tetrahedron Lett. 2010; 51: 6255;
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H
19 1
Chem. 1996; 108: 57;
3
) δ: 7.23 (t, J =
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13
8
(
453;
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Inorg Chim Acta. 2007; 360: 656;
i) De Rosa M, Lamberti M, Pellecchia C, Scettri A,
(m, 2H), 2.82-2.78 (m, 2H); C NMR (100 MHz, CDCl3): δ
137.7, 127.9, 127.5, 125.7, 52.8, 28.0; HRMS (EI): calc.for
C H18OS 258.1078, found 258.1074.
16
(
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2
4. General procedure for the synthesis of sulfoxides 3: A mixture
of olefin 1 (1 mmol), NHPI (10 mol%), thiol 2 (1 mmol) and
acetonitrile (3 mL) was stirred at rt under air and irradiation
with visible light (7 W white light emitting diodes) ( 7 W
LEDs) for 8-12 h ( Table 2). After completion of reaction
(monitored by TLC), water (5 mL) was added and the
mixture was extracted with ethyl acetate (3 × 5 mL). The