SRN1 Reactions of Halocyclopropanes with Benzenethiolate Ion

Article abstract of DOI:10.1021/jo00355a007

Ultraviolet irradiation of gem-dibromocyclopropanes 1 with benzenethiolate ion in liquid ammonia or in Me2SO solutions gave dithioacetals 2 and, in some cases, cyclopropyl phenyl sulfides 3.The reactions did not proceed in the dark and they were inhibited by m-dinitrobenzene, di-tert-butyl nitroxide, and oxygen.The bromocyclopropane 6a underwent a similar, but slower, reaction.Treatment of the bromochlorocyclopropane 7b led to replacement of only the bromine, while the dichlorocyclopropane 9b was inert under the reaction conditions.The results appear consistent with a radical chain mechanism.