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

Philip Burke, Lai Chun Wong, William Clegg, Ross Harrington, Terence Jenkins, Richard Knox, Ian Meikle, Stephen Stanforth

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)3918-3921
JournalTetrahedron Letters
Volume51
Issue number30
DOIs
Publication statusPublished - 28 Jul 2010

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