The phosphorylation of 2-vinyl- and 4-vinylpyridines by white phosphorus and active modifications of red phosphorus (obtained by thermal polymerization of white phosphorus in the presence of graphite or the action of ionizing radiation in benzene) in the KOH/DMSO superbase system at room temperature leads to the formation of tris[2-(2-pyridyl)ethyl]- and tris[2-(4-pyridyl)ethyl]phosphine oxides in 58-72% yield. These oxides are promising ligands for design of metal complex catalysts. These vinylpyridines react less efficiently with ordinary red phosphorus and the yield of the corresponding tris(2-pyridylethyl)phosphine oxides does not exceed 10%.
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.
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.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInformVolume 21, Issue 51 Organoelement Compounds ChemInform Abstract: Reaction of Red Phosphorus with Electrophiles in Superbasic Systems. Part 2. Synthesis of Triorganylphosphine Oxides from Red Phosphorus and Organyl Halides. N. K. GUSAROVA, N. K. GUSAROVA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorS. F. MALYSHEVA, S. F. MALYSHEVA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorT. N. RAKHMATULINA, T. N. RAKHMATULINA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorV. I. DMITRIEV, V. I. DMITRIEV Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorS. I. SHAIKHUDINOVA, S. I. SHAIKHUDINOVA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorL. M. SINEGOVSKAYA, L. M. SINEGOVSKAYA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorB. A. TROFIMOV, B. A. TROFIMOV Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this author N. K. GUSAROVA, N. K. GUSAROVA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorS. F. MALYSHEVA, S. F. MALYSHEVA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorT. N. RAKHMATULINA, T. N. RAKHMATULINA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorV. I. DMITRIEV, V. I. DMITRIEV Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorS. I. SHAIKHUDINOVA, S. I. SHAIKHUDINOVA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorL. M. SINEGOVSKAYA, L. M. SINEGOVSKAYA Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this authorB. A. TROFIMOV, B. A. TROFIMOV Irkutsk. inst. org. khim. Sib. otd. AN SSSR, USSRSearch for more papers by this author First published: December 18, 1990 https://doi.org/10.1002/chin.199051242Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat No abstract is available for this article. References N. K. GUSAROVA, S. F. MALYSHEVA, T. N. RAKHMATULINA, V. I. DMITRIEV, S. I. SHAIKHUDINOVA, L. M. SINEGOVSKAYA, B. A. TROFIMOV, Reaction of Red Phosphorus with Electrophiles in Superbasic Systems. Part 2. Synthesis of Triorganylphosphine Oxides from Red Phosphorus and Organyl Halides., Zh. Obshch. Khim., 1990, 60(122), 828–832. Web of Science®Google Scholar Volume21, Issue51December 18, 1990 ReferencesRelatedInformation
ChemInformVolume 21, Issue 14 Organoelement Compounds ChemInform Abstract: Reaction of Red Phosphorus with Allyl Halides Under Phase-Transfer Catalysis. B. A. TROFIMOV, B. A. TROFIMOV Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorS. F. MALYSHEVA, S. F. MALYSHEVA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorN. K. GUSAROVA, N. K. GUSAROVA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorV. I. DMITRIEV, V. I. DMITRIEV Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorS. I. SHAIKHUDINOVA, S. I. SHAIKHUDINOVA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorT. N. RAKHMATULINA, T. N. RAKHMATULINA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorV. I. DONSKIKH, V. I. DONSKIKH Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorM. G. VORONKOV, M. G. VORONKOV Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this author B. A. TROFIMOV, B. A. TROFIMOV Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorS. F. MALYSHEVA, S. F. MALYSHEVA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorN. K. GUSAROVA, N. K. GUSAROVA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorV. I. DMITRIEV, V. I. DMITRIEV Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorS. I. SHAIKHUDINOVA, S. I. SHAIKHUDINOVA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorT. N. RAKHMATULINA, T. N. RAKHMATULINA Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorV. I. DONSKIKH, V. I. DONSKIKH Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this authorM. G. VORONKOV, M. G. VORONKOV Irkutsk. inst. org. khim. Sib. otd. AN SSSRSearch for more papers by this author First published: April 3, 1990 https://doi.org/10.1002/chin.199014217Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume21, Issue14April 3, 1990 RelatedInformation