Tetrahedron p. 527 - 537 (1982)
Update date:2022-08-05
Topics:
Morel, G.
Lemoing-Orliac, M. A.
Khamsitthideth, S.
Foucaud, A.
Reactions of substituted cyanoacetate anions 4 with S,S-dialkylsuccinimidosulfonium 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 ?-sulfurane intermediates.Homolytic cleavage of these intermediates gave radical pairs, then the coupling products.Heterolytic cleavage gave new sulfonium salts which rearranged via sulfonium ylides.
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Doi:10.1016/j.tet.2004.10.017
(2004)Doi:10.1055/s-1982-29769
(1982)Doi:10.1007/BF00580446
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(1983)Doi:10.1039/b918103b
(2010)
