Reaction of gem-Dibromocyclopropanes with Potassium Dimethyl Phosphite in Liquid Ammonia. A Highly Stereoselective Reduction

Article abstract of DOI:10.1021/jo00220a008

Although gem-dibromocyclopropanes undergo subsitution with other S_RN1 nucleophiles in liquid ammonia solution stimulated by "350 nm" light, only reduction is observed with dimethyl phosphite ion.This reduction proceeds in the absence of light and involves nonradical intermediates.It gives high yields of the trans monobromides 4 with little or no contamination by the cis isomers 5 or the direduced products 6. gem-Dichlorocyclopropanes are inert under the reaction conditions.The reaction is suited to preparative work.