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Typical data for representative compound:
4-isopropylthioanisole (Table 2, entry 3)
Colorless oil; 1 H NMR (300 MHz, CDCl3): δ 7.21-7.19 (d, J = 8.4Hz, 2 H),
7.15-7.12 (d, J = 8.4 Hz, 2 H), 2.87-2.83 (m, 1 H), 2.44 (s, 3 H), 1.22 (d, J = 6.9
Hz, 6 H). 13 C NMR (75 MHz, CDCl3): δ 146.1, 135.2, 127.3, 127.0, 33.7, 24.0,
16.4. GC-MS (EI, m/z): 166 [M+]
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22. General procedure
Diaryl disulfide (0.5 mmol), DTBP (3.0 mmol) and CH3CN (2.0 mL) were
taken in a 25 mL Schlenk round-bottomed flask. The reaction mixture was
stirred at 120 °C for 12 hours under a nitrogen atmosphere. After cooling to
room temperature, the product was diluted with H2O (5 mL) and extracted
with EtOAc (4×10 mL). The extracts were combined and washed by brine
(3×10 mL), dried over MgSO4, filtered, and evaporated, and purified by
chromatography on silica gel to obtain the desired products with ethyl
acetate/hexane (v/v=1:30~1:100). The products were characterized by their