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

Marie Kissane; Maureen Murphy; Denis Lynch; Alan Ford; Anita R. Maguire

doi:10.1016/j.tet.2008.05.026

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

Marie Kissane
, Maureen Murphy
, Denis Lynch
, Alan Ford
, Anita R. Maguire

Analytical and Biological Chemistry Research Facility

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	7639-7649
Number of pages	11
Journal	Tetrahedron
Volume	64
Issue number	32
DOIs	https://doi.org/10.1016/j.tet.2008.05.026
Publication status	Published - 4 Aug 2008

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https://hdl.handle.net/10468/586Licence: CC BY-NC-ND

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title = "Investigation of the reaction of α-thioamides, α-esters and α-nitriles with N-halosuccinimides",

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.",

author = "Marie Kissane and Maureen Murphy and Denis Lynch and Alan Ford and Maguire, \{Anita R.\}",

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T1 - Investigation of the reaction of α-thioamides, α-esters and α-nitriles with N-halosuccinimides

AU - Kissane, Marie

AU - Murphy, Maureen

AU - Lynch, Denis

AU - Ford, Alan

AU - Maguire, Anita R.

PY - 2008/8/4

Y1 - 2008/8/4

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/45649085495

U2 - 10.1016/j.tet.2008.05.026

DO - 10.1016/j.tet.2008.05.026

M3 - Article

AN - SCOPUS:45649085495

SN - 0040-4020

VL - 64

SP - 7639

EP - 7649

JO - Tetrahedron

JF - Tetrahedron

IS - 32

ER -

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

Abstract

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