Selective transformation of α,α-dibromomethyl ketones into α-monosulfenylated ketones

Article abstract of DOI:10.1016/S0040-4020(01)89544-2

When α,α-dibromomethyl ketones are treated with sodium thiolates only the α-monosulfenylated ketones are formed. Evidence is put forward that the reaction mechanism proceeds by an initial nucleophilic substitution of one bromo atom and reduction by single electron transfer (SET) - hydrogen atom abstraction of the second bromo atom.