Addition nucleophile des anions d'esters α-cyanoacetiques sur les cations succinimidosulfonium: Fragmentation ionique ou radicalaire des′ σ-sulfuranes intermediaires |
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Authors: | G. Morel M.A. LeMoing-Orliac S. Khamsitthideth A. Foucaud |
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Affiliation: | Groupe de Recherches de Physicochimie Structurale, équipe assocée au CNRS No. 389, Université de Rennes, Campus de Beaulieu, 35042 Rennes, France |
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Abstract: | Reactions of substituted cyanoacetate anions 4 with S,S-dialayklsuccinimidosulfonium salts resulted generally in the formation of N-alkylthiomethylketenimines and α-alkylthiomethylesters. Coupling products were also obtained with anion 4d and only observed in the case of methyl phenylcyanoacetate anion 4b. The results were interpreted by the formation of instable σ-sulfurane intermediates. Homolytic cleavage of these intermediates gave radical pairs, then the coupling products. Heterocyclic clevage gave new sulfonium salts which rearranged via sulfonium ylides. |
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