Tetrahedron

Ligand exchange reaction of sulfoxides in organic synthesis: A novel method for synthesizing acetylenes and allenes from carbonyl compounds through sulfoxides …

…, N Itoh, S Watanabe, H Koike, H Matsuno, K Matsuda…

Index: Satoh, Tsuyoshi; Itoh, Norifumi; Watanabe, Shizue; Koike, Hirofumi; Matsuno, Haruko; Matsuda, Kenji; Yamakawa, Koji Tetrahedron, 1995 , vol. 51, # 34 p. 9327 - 9338

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Citation Number: 26

Abstract

A novel method for synthesizing acetylenes and allenes from carbonyl compounds is described. Ligand exchange reaction of alkenylsulfoxides having a trifluoromethanesulfonyloxy group on the β-carbon, which were derived from α-alkyl β- ketosulfoxides, with n-BuLi gave disubstituted acetylenes in good yields. In the case of alkenylsulfoxides having both the trifluoromethanesulfonyloxy and aryl groups on the β- ...