Phthalimidosulphenyl chloride: A synthetic equivalent of inaccessible sulphenyl chlorides

Abstract

The phthalimido derivative 3a, synthesized by addition of phthalimidosulphenyl chloride 1 to 2-butyne, reacts with variuos nucleophiles (t-BuLi, MeLi, PhLi, t-Bu-C=CLi, (Me 3Si) 2NNa) to give substitution of the phthalimido residue. Tri-n-butyltin hydride, in the presence of a radical initiator, also reacts with 3a and gives the tri-n-butyltin-vinylsulphide 9. The stereo and regiochemical course of the addition of 1 to several alkynes was found to be similar to that of simple alkane or arenesulphenyl chlorides.