Reactivity of phosphonium diylids with esters and amides

The phosphonium diylid (C 6H 5) 2P(CH 2)(CH 2Li) reacts readily with various esters and amides to give acylated phosphonium salts and Wittig products. In the case of N, N-dimethylbenzamide the reaction can be directed mainly to the Wittig products by protonation. Depending on the nature of the carbo...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 352; no. 3; pp. C51 - C53
Main Authors Cristau, Henri-Jean, Ribeil, Yves
Format Journal Article
LanguageEnglish
Published Lausanne Elsevier B.V 13.09.1988
Elsevier Science
Subjects
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
Wittig reaction
Carboxamide
Organic phosphorane
Phosphorus Organic compounds
Vinylic compound
Ylide
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Summary:The phosphonium diylid (C 6H 5) 2P(CH 2)(CH 2Li) reacts readily with various esters and amides to give acylated phosphonium salts and Wittig products. In the case of N, N-dimethylbenzamide the reaction can be directed mainly to the Wittig products by protonation. Depending on the nature of the carbonyl group, unexpected reactions, such as conjugate additions to α,β-unsaturated compounds or enolization of α-hydrogenated amides, can also take place.
ISSN:0022-328X
1872-8561
DOI:10.1016/0022-328X(88)83132-2