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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

✍ Scribed by Michael J. Donaghy; Stephen P. Stanforth

Publisher: Journal of Heterocyclic Chemistry
Year: 2005
Tongue: English
Weight: 79 KB
Volume: 42
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570420629

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✦ Synopsis

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 4toluenesulfonyl chloride giving the tosylate 16 under similar conditions.

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