Synthesis and reactions of 2, 6-diphenyl-4-(trimethylsilyl)-4H-thiopyran

CH Chen, JJ Doney, GA Reynolds

Index: Chen, Chin H.; Doney, Jeffrey J.; Reynolds, George A. Journal of Organic Chemistry, 1982 , vol. 47, # 4 p. 680 - 684

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Citation Number: 18

Abstract

The title compound 3 was synthesized by trimethylsilyl chloride quenching of 2, 6-diphenyl- 4lithie4H-thiopyran (7), which was obtained by direct lithiation (n-BuLi) of either the 4H- thiopyran 10 or the W isomer 6. Compound 6 was readily prepared in one step from the reaction of 2, 6-diphenyl-4-hydroxy-4H-thiopyran (5) with NCS in 74% yield. Compound 3 was metalated to give 12 in W85% yield by using a combination of n-BuLi and t-BuOK in ...