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 ...