Syntheses with ethynylphosphonium salts; nucleophilic additions to phenylethynyltriphenylphosphoniun bromide

Abstract

Acyclic and heterocyclic adducts have been prepared by additions to phenylethynyltriphenylphosphoniun bromide of behnoylhydrazine, hydroxylamine, o-aminobenzophenone, o-aminophenol, o-aminobenzenethiol, o-aminoaniline, ethylenediamine, 2, 3-diamionopyridine, 1, 2-diaminonaphthalene, 1, 8-diaminonaphthalene, and benzophenone hydrazone. A useful feature of the title compounds is that the triphenylphosphonium group activtes the triple bond and then can be removed either as phosphine oxide or as a quaternary salt; thus, they are potential ethynyl equivalents.