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

Michael Donaghy; Stephen Stanforth

doi:10.1002/jhet.5570420629

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

Michael Donaghy, Stephen Stanforth

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1215-1218
Journal	Journal of Heterocyclic Chemistry
Volume	42
Issue number	6
DOIs	https://doi.org/10.1002/jhet.5570420629
Publication status	Published - Sept 2005

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10.1002/jhet.5570420629

http://onlinelibrary.wiley.com/doi/10.1002/jhet.5570420629/abstract

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title = "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",

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.",

author = "Michael Donaghy and Stephen Stanforth",

year = "2005",

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T1 - 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

AU - Donaghy, Michael

AU - Stanforth, Stephen

PY - 2005/9

Y1 - 2005/9

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/24944554894

U2 - 10.1002/jhet.5570420629

DO - 10.1002/jhet.5570420629

M3 - Article

SN - 0022-152X

SN - 0931-7597

SN - 1943-5193

VL - 42

SP - 1215

EP - 1218

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

IS - 6

ER -

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

Abstract

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