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)

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