Intermediacy of o-Sulfonylium Arenide Ylides in the Reactions of Arenesulfonyl Derivatives with Strong Bases: Insight into the Puzzling Rearrangement of N- …

JJ Eisch, Y Qian, CS Chiu

Index: Eisch, John J.; Qian, Yun; Chiu, Chingchen S. Journal of Organic Chemistry, 1996 , vol. 61, # 4 p. 1392 - 1398

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Citation Number: 2

Abstract

Benzenesulfonyl derivatives, PhSO2E, such as benzenesulfonyl fluoride, phenyl benzenesulfonate, and N-methyl-N-phenylbenzenesulfonamide, have been found to undergo ortho-lithiation with lithium 2, 2, 6, 6-tetramethylpiperidide (LTMP) in THF at-78° C. The resulting lithio derivatives undergo 1, 3-elimination of LiE to form the transient o- sulfonylium benzenide. The latter ylide, which may be stabilized by its carbenoid character ...