Silicon in organic synthesis. 24. Preparation and selected reactions of functionalized 1-(trimethylsilyl)-substituted cyclopropanes

GJ Wells, TH Yan, LA Paquette

Index: Wells, Gregory J.; Yan, Tu-Hsin; Paquette, Leo A. Journal of Organic Chemistry, 1984 , vol. 49, # 19 p. 3604 - 3609

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Citation Number: 38

Abstract

Several methods for preparing bifunctional 1-(trimethylsily1)-substituted cyclopropanes are described. The methyl bromide 4, available by SimmonsSmith cyclopropanation of 2 and bromination with phosphorus tribromide, is shown to be highly reactive to SN~ displacement and therefore easily transformed into a variety of other derivatives including the phenyl sulfide, phenyl sulfone, nitrile, and phenyl selenide. Ring-closure protocols have been ...