An unusual substitution reaction directed by an intramolecular re-arrangement

Parenty, A.D.C., Smith, L.V. and Cronin, L. (2005) An unusual substitution reaction directed by an intramolecular re-arrangement. Tetrahedron, 61(35), pp. 8410-8418. (doi:10.1016/j.tet.2005.06.074)

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Publisher's URL: http://dx.doi.org/10.1016/j.tet.2005.06.074

Abstract

Secondary amines and thiols undertake a substitution reaction on the side chain of 2-bromoethyl-pyridinium derivatives ‘directed’ by an intramolecular re-arrangement. Experimental investigations strongly indicate that the reaction is initiated by an alpha addition of the nucleophile onto the iminium moiety of the N-heteroaromatic cation, followed by a cyclisation and an oxidative ring opening. This novel substitution process is able to occur with less reactive nucleophiles that would not undergo conventional substitution with ‘isolated’ bromoethyl moieties.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Parenty, Mr Alexis and Cronin, Professor Lee
Authors: Parenty, A.D.C., Smith, L.V., and Cronin, L.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
University Centres > Glasgow Materials Research Initiative
Journal Name:Tetrahedron
ISSN:0040-4020

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