The chemistry of small ring compounds. Part 43. Synthesis of 1‐substituted cyclopropyl sulfides

Abstract 1‐Hydroxy‐ and 1‐halocyclopropyl sulfides can be conveniently prepared starting from cyclopropanone. Cyclopropyl sulfides with halogen or a dimethylsulfonium group in the α‐position can be transformed into 1‐substituted cyclopropyl sulfides with a variety of nucleophiles. This means that the usual difficulties encountered with nucleophilic substitution at three‐membered rings ‐ i.e. low rates and ring opening — are largely removed by the presence of an alkylthio group at the same ring carbon atom as the leaving group.