A Facile and Convergent Synthesis of γ-Unsaturated Substituted Sulfines

Jean-Bernard Baudin; Marie-Gabrielle Commenil; Sylvestre A. Julia; Yuan Wang

doi:10.1055/s-1992-21538

Synlett 1992; 1992(11): 909-910
DOI: 10.1055/s-1992-21538

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A Facile and Convergent Synthesis of γ-Unsaturated Substituted Sulfines

Jean-Bernard Baudin^* , Marie-Gabrielle Commenil, Sylvestre A. Julia, Yuan Wang

^*Laboratoire de Chimie, Ecole Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France

Abstract

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A new synthesis of the title thioaldehyde and thioketone S-oxides is described: by treatment of vinylic or allenic sulfinates with allylic Grignard reagents, or allylic sulfinates with vinylic Grignard reagents. Some α,β-ethylenic thioaldehyde S-oxides undergo in situ a cycloaromatisation into thiophenes 12a,b. Reaction of allenic sulfinates with secondary vinylic Grignard derivatives afforded the γ-acetylenic thioketone S-oxides 14a-d.

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