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

Full text not available from this repository. (Request a copy)

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:	12 Oct 2019 17:30
URI:	http://nrl.northumbria.ac.uk/id/eprint/19839

Downloads