Reactions of elemental phosphorus and phosphine with electrophiles in superbasic systems: XIV. 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 90-96degreesC 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-naph...

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Published inRussian journal of general chemistry Vol. 72; no. 3; pp. 371 - 375
Main Authors Gusarova, NK, Shaikhutdinova, SI, Kazantseva, TI, Malysheva, SF, Sukhov, BG, Belogorlova, NA, Dmitriev, Trofimov, BA
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.03.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ORGANOPHOSPHORUS COMPOUNDS
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Summary:Elemental phosphorus (red or white) reacts with 2-vinylnaphthalene while heating at 90-96degreesC 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.
ISSN:1070-3632
1608-3350
DOI:10.1023/A:1015483315244