The Journal of Organic Chemistry

Phase-transfer-catalyzed oxidation and reduction of organosulfur compounds with dichlorocarbene. Mechanism and synthetic utility

JC Dyer, SA Evans Jr

Index: Dyer, John C.; Evans, Slayton A. Journal of Organic Chemistry, 1980 , vol. 45, # 26 p. 5350 - 5355

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Citation Number: 11

Abstract

Diary1 ant1 dialkyl Sulfoxides undergo facile phase-transfer-catalyzed (F'TC) deoxygenation with dichlorocarbene at 25 OC to afford excellent yields of sulfides. Comparisons of deoxygenation rates of dialkyl and diaryl sulfoxides suggest that steric acceleration occurs with the bulky sulfoxides while resonance interactions from aromatic rings retard the reduction. Less bulky sulfides also undergo the reverse reaction: addition of ...