Citation:KISSANE, M., MURPHY, M., LYNCH, D., FORD, A. & MAGUIRE, A. R. 2008. Investigation of the reaction of α-thioamides, α-esters and α-nitriles with N-halosuccinimides. Tetrahedron, 64, 7639-7649. doi: 10.1016/j.tet.2008.05.026
Investigation of the reaction of α-thioamides, α-esters and α-nitriles with NBS and NCS is described. The scope of this stereoselective oxidative transformation to the β-
haloacrylamides, β-acrylates and β–acrylonitriles has been determined. A mechanistic rationale to explain the observed differences in reactivity between the amide, ester and
nitrile series is proposed.
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