Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Systems: XIV.1 Phosphorylation of 2-Vinylnaphthalene with Elemental Phosphorus and Phosphines in the KOH-DMSO System

Elemental phosphorus (red or white) reacts with 2-vinylnaphthalene while heating at 90-96°C in the superbasic KOH-DMSO system to form 2-(2-naphthyl)ethylphosphine, 2-(2-naphthyl)ethylphosphinic acid, bis[2-(2-naphthyl)ethyl]phosphine, bis[2-(2-naphthyl)ethyl]phosphine oxide, and tris[2-(2-naphthyl)ethyl]phosphine oxide in a total yield of up to 40%. Selective conditions for preparing the tertiary phosphine oxide from white phosphorus and 2-vinylnaphthalene in 58% yield were found. Phosphine and (2-phenylpropyl)phosphine add to 2-vinylnaphthalene in the KOH-DMSO system to form, under certain conditions, corresponding secondary phosphines in high yields.