An unexpected ring contraction of two nitroaryl pro-drugs: conversion of N-(nitroaryl)-3-chloropiperidine derivatives into N-(nitroaryl)-2-chloromethylpyrrolidines

Burke, Philip, Wong, Lai Chun, Clegg, William, Harrington, Ross, Jenkins, Terence, Knox, Richard, Meikle, Ian and Stanforth, Stephen (2010) An unexpected ring contraction of two nitroaryl pro-drugs: conversion of N-(nitroaryl)-3-chloropiperidine derivatives into N-(nitroaryl)-2-chloromethylpyrrolidines. Tetrahedron Letters, 51 (30). pp. 3918-3921. ISSN 0040-4039

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2010.05.095

Abstract

Treatment of the N-nitroaryl-3-hydroxypiperidine derivatives 12 and 13 with thionyl chloride afforded the corresponding N-aryl-2-chloromethylpyrrolidines 5 and 15 via a ring-contraction process involving an intermediate aziridinium ion.

Item Type: Article
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: EPrint Services
Date Deposited: 29 Mar 2011 08:51
Last Modified: 10 Aug 2015 11:41
URI: http://nrl.northumbria.ac.uk/id/eprint/2213

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