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An unexpected ring contraction of two nitroaryl pro-drugs: conversion of N-(nitroary1)-3-chloropiperidine derivatives into N-(nitroaryl)-2-chloromethylpyrrolidines

Lookup NU author(s): Emeritus Professor Bill CleggORCiD, Dr Ross Harrington

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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. (C) 2010 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Burke PJ, Wong LC, Clegg W, Harrington RW, Jenkins TC, Knox RJ, Meikle IT, Stanforth SP

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2010

Volume: 51

Issue: 30

Pages: 3918-3921

Print publication date: 27/05/2010

ISSN (print): 0040-4039

ISSN (electronic): 1873-3581

Publisher: Pergamon

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

DOI: 10.1016/j.tetlet.2010.05.095

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