Chemoselective Reaction of Red Phosphorus with 4-Vinylbenzyl Chloride:A Convenient Route to Tris(4-vinylbenzyl)phosphine Oxide

摘要

Direct phosphorylation of electrophiles with elemental phosphorus in superbasic medium such as alkali metal hydroxide-polar nonhydroxylic solvent (DMSO,HMPA)or alkali metal hydroxide-aqueous-organic emulsion-phase-transfer catalyst opened a convenient route to formation of a C-P bond and synthesis of previously unknown or difficultly available organophosphorus compounds,primarily organic phosphines and phosphine oxides [1-7].For example,tribenzyl- and tris(2-phenylethyl)phosphine oxides were prepared from red phosphorus and benzyl chloride [8]and styrene [9],respectively,in the presence of strong bases in high yield (50-60%).