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

doi:10.1016/j.tetlet.2010.05.095

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 journal › Article › peer-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 language	English
Pages (from-to)	3918-3921
Journal	Tetrahedron Letters
Volume	51
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2010.05.095
Publication status	Published - 28 Jul 2010

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

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.",

author = "Philip Burke and Wong, \{Lai Chun\} and William Clegg and Ross Harrington and Terence Jenkins and Richard Knox and Ian Meikle and Stephen Stanforth",

year = "2010",

month = jul,

day = "28",

doi = "10.1016/j.tetlet.2010.05.095",

language = "English",

volume = "51",

pages = "3918--3921",

journal = "Tetrahedron Letters",

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T1 - An unexpected ring contraction of two nitroaryl pro-drugs: conversion of N-(nitroaryl)-3-chloropiperidine derivatives into N-(nitroaryl)-2-chloromethylpyrrolidines

AU - Burke, Philip

AU - Wong, Lai Chun

AU - Clegg, William

AU - Harrington, Ross

AU - Jenkins, Terence

AU - Knox, Richard

AU - Meikle, Ian

AU - Stanforth, Stephen

PY - 2010/7/28

Y1 - 2010/7/28

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/77953809477

U2 - 10.1016/j.tetlet.2010.05.095

DO - 10.1016/j.tetlet.2010.05.095

M3 - Article

SN - 0040-4039

VL - 51

SP - 3918

EP - 3921

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

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

Abstract

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