Reaction of Red Phosphorus with Allylbenzene in Superbasic System KOH-DMSO

Svetlana F. Malysheva A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Natal’ya A. Belogorlova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Nina K. Gusarova A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Alexander V. Artem’ev A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Alexander I. Albanov A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Boris A. Trofimov A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

Abstract

Red phosphorus reacts with allylbenzene in the superbase system KOH-DMSO (130°C, 3 h, Ar) to give a mixture of bis(1-methyl-2-phenylethyl)phosphane (1), bis(1-methyl-2-phenylethyl)phosphane oxide (2), and 1-methyl-2-phenylethylphosphinic acid (3). Secondary phosphane oxide 2 and phosphinic acid 3 have been isolated from this mixture in 35% and 32% yield, respectively. Microwave activation of the reaction (200 W, 30 min) affords secondary phosphane 1 as the main product in 48% yield.

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Financial support from the Russian Foundation for Basic Research (grant no. 08-03-00251) is gratefully acknowledged.

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Reaction of Red Phosphorus with Allylbenzene in Superbasic System KOH-DMSO

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Reaction of Red Phosphorus with Allylbenzene in Superbasic System KOH-DMSO

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