Journal of Organic Chemistry p. 606 - 611 (1986)
Update date:2022-07-30
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Meijs, Gordon F.
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.
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