REDUCTIVE REMOVAL OF HALOGEN BY THIOLATES FROM 1-HALOCYCLO-PROPYL SULFIDES

Abstract

Nucleophilic substitution of cyclopropyl halides or tosylates is often accompanied by ring rupture, but this can be prevented by the presence of an electron releasing substituent in α-position (NR₂, OR, SR). Alkylthio and arylthio groups are particularly effective in stabilizing intermediate cyclopropyl cations. These give with most nucleophiles e.g. alkoxide, azide, fluoride, in relatively rapid reactions good yields of substitution products.