Reaction of 1-bromonaphthalene with PH3 in the t-BuOK/DMSO system: PCl3-free synthesis of di(1-naphthyl)phosphine and its oxide

The phosphine, generated together with hydrogen from red phosphorus and aqueous KOH, reacts with 1-bromonaphthalene in the t-BuOK/DMSO system under mild conditions (70 °C, atmospheric pressure) to give di(1-naphthyl)phosphine, which is easily oxidized in the presence of air to afford di(1-naphthyl)p...

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Bibliographic Details
Published in:Tetrahedron 2017-08, Vol.73 (32), p.4723-4729
Main Authors: Kuimov, Vladimir A., Matveeva, Elena A., Khutsishvili, Spartak S., Vakul'skaya, Tamara I., Sinegovskaya, Lidiya M., Malysheva, Svetlana F., Gusarova, Nina K., Trofimov, Boris A.
Format: Article
Language:English
Subjects:
1-Bromonaphthalene
Di(1-naphthyl)phosphine
Di(1-naphthyl)phosphine oxide
Phosphine
Single electron transfer
Superbase system
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Summary:The phosphine, generated together with hydrogen from red phosphorus and aqueous KOH, reacts with 1-bromonaphthalene in the t-BuOK/DMSO system under mild conditions (70 °C, atmospheric pressure) to give di(1-naphthyl)phosphine, which is easily oxidized in the presence of air to afford di(1-naphthyl)phosphine oxide in 45% preparative yield. Tri(1-naphthyl)phosphine and naphthalene are also formed in the reaction in 23 and 27% yield, respectively. According to ESR and UV data, the studied phosphination of 1-bromonaphthalene involves a single electron transfer process. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.06.036