Reactions of elemental phosphorus and phosphine with electrophiles in superbasic systems: XX. Phosphorylation of 4-vinylbenzyl chloride with elemental phosphorus

Abstract

4-Vinylbenzyl chloride reacts with white and red phosphorus, as well as with nanostructured “activated” red phosphorus (complex organophosphorus polymer prepared from white phosphorus under ionizing radiation) in the system concentrated aqueous KOH-dioxane-phase-transfer catalyst (20–50°C, argon) to form tris(4-vinylbenzyl)phosphine oxide, along with (4-vinylbenzyl)- and bis(4-vinylbenzyl)phosphinic acids, the yield and product ratio being dependent on both the reaction conditions and the nature of the phosphorylating agent. The nanostructured “activated” red phosphorus is more reactive than ordinary commercial red phosphorus.