Tetrahedron Letters

Preparation and ring-opening reactions of 2-phenylsulphonyl-2-trimethylsilyl-oxiranes

CT Hewkin, RFW Jackson

Index: Hewkin, Cheryl T.; Jackson, Richard F. W. Tetrahedron Letters, 1990 , vol. 31, # 13 p. 1877 - 1880

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Citation Number: 25

Abstract

Abstract Reaction of 2-phenylsulphonyl oxiranes (1) with butyllithium in the presence of chlorotrimethylsilane gave 2-phenylsulphonyl-2-trimethylsilyl oxiranes (2), which on treatment with MgBr 2 Et 2 O gave 2-bromoacylsilanes (3) and either bromovinyl sulphones (5) or α, β-unsaturated acylsilanes (6) and 2-trimethylsilyl car☐ ylic acids (7), depending on structure.