Possible neighbouring group participation of a nitro-group in the conversion of 3-hydroxymethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline into its 3-chloromethyl derivative

Donaghy, Michael and Stanforth, Stephen (2005) Possible neighbouring group participation of a nitro-group in the conversion of 3-hydroxymethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline into its 3-chloromethyl derivative. Journal of Heterocyclic Chemistry, 42 (6). pp. 1215-1218. ISSN 0022-152X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/jhet.55...

Abstract

The alcohol 12 reacted with 4-toluenesulfonyl chloride in boiling dichloromethane solution to give the chlorinated product 13 rather than the expected tosylate 3 by a mechanism that could involve neighbouring group participation of the nitro-substituent. In contrast, the isomeric alcohol 15 reacted normally with 4-toluenesulfonyl chloride giving the tosylate 16 under similar conditions.

Item Type: Article
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > Applied Sciences
Depositing User: Becky Skoyles
Date Deposited: 02 Feb 2015 13:50
Last Modified: 24 Oct 2017 11:28
URI: http://nrl.northumbria.ac.uk/id/eprint/19839

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