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Elsevier, Tetrahedron Letters, 30(51), p. 3918-3921

DOI: 10.1016/j.tetlet.2010.05.095

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

Journal article published in 2010 by Philip J. Burke, Lai Chun Wong, William Clegg ORCID, Ross W. Harrington, Terence C. Jenkins, Richard J. Knox, Ian T. Meikle, Stephen P. Stanforth
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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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.