Reactions of Elemental Phosphorus and Phosphine with Electrophiles in Superbasic Media: XI.1 Phosphorylation of 4-Methoxybenzyl Chloride with Elemental Phosphorus and Phosphine |
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Authors: | Shaikhutdinova S I Kazantseva T I Gusarova N K Dmitriev V I Trofimov B A |
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Institution: | (1) Favorskii Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia;(2) Irkutsk State University, Irkutsk, Russia |
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Abstract: | 4-Methoxybenzyl chloride reacts with elemental (red or white) phosphorus under the conditions of phase-transfer catalysis (concentrated aqueous KOH, dioxane, benzyltriethylammonium chloride, 85-90°C, argon) to give as major product tris(4-methoxybenzyl)phosphine oxide in up to 45% yield. With white phosphorus at lower (70°C) temperature this reaction yields mainly bis(4-methoxybenzyl)phosphine oxide. Phosphine reacts with 4-methoxybenzyl chloride in superbasic KOH-DMSO suspension, and under definite conditions bis(4-methoxybenzyl)phosphine oxide is predominantly formed. |
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