Investigation of the reaction of α-Thioamides, α-esters and α–nitriles with N-halosuccinimides
Maguire, Anita R.
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.
alpha-thioamides , alpha-esters , alpha-nitriles , N-Bromosuccinimide(NBS) , N-Chlorosuccinimide (NCS) , beta-haloacrylamides , beta-acrylates , beta–acrylonitriles
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
Copyright © 2008 Elsevier Ltd. All rights reserved. NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, [VOL 64, ISSUE 32, (04/08/2008)] DOI 10.1016/j.tet.2008.05.026