Investigation of the reaction of α-Thioamides, α-esters and α–nitriles with N-halosuccinimides

Files in this item

Icon
Name: MK_InvestigationS ...
Size: 409.3Kb
Format: PDF
Description: Submitted Version
View/Open

Investigation of the reaction of α-Thioamides, α-esters and α–nitriles with N-halosuccinimides

Kissane, Marie; Murphy, Maureen; Lynch, Denis; Ford, Alan; Maguire, Anita R.
Date: 2008-08-04
Copyright: 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
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
Published Version: 10.1016/j.tet.2008.05.026

Abstract:

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.

Show full item record

This item appears in the following Collection(s)

This website uses cookies. By using this website, you consent to the use of cookies in accordance with the UCC Privacy and Cookies Statement. For more information about cookies and how you can disable them, visit our Privacy and Cookies statement