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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
Author(s) -
Donaghy Michael J.,
Stanforth Stephen P.
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420629
Subject(s) - chemistry , dichloromethane , hydroxymethyl , substituent , nitro , alcohol , derivative (finance) , group (periodic table) , medicinal chemistry , tetrahydroisoquinoline , chloride , organic chemistry , solvent , alkyl , financial economics , economics
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.