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

Add time:07/13/2019    Source:sciencedirect.com

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.

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