Kissane, M, Murphy, M, Lynch, D, Ford, A, Maguire, AR;

2008

August

Tetrahedron

Investigation of The Reaction of alpha-Thioamides, alpha-Esters and alpha-Nitriles With N-Halosuccinimides

Validated

()

64

32

7639

7649

investigation of the reaction of alpha-thioamides, alpha-esters and alpha-nitriles with NBS and NCS is described. The scope of this stereoselective oxidative transformation to the beta-haloacrylamides, beta-acrylates and beta-acrylonitriles has been determined. A mechanistic rationale to explain the observed differences in reactivity between the amide, ester and nitrile series is proposed. (C) 2008 Elsevier Ltd. All rights reserved..

DOI 10.1016/j.tet.2008.05.026