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Pyridine‐4‐thiol and Amphoteric Analogs: Novel Protection of Aryl Bromides in Strong Alkali
Author(s) -
Chen WeiMin,
Cheng Chao,
Li BingZhou,
Ho TseLok,
Cai ZhaoShuo,
Wang Yuqiang,
Sun PingHua
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890219
Subject(s) - chemistry , alkoxide , alkali metal , pyridine , aryl , thiol , hydroxide , substituent , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , alkyl
The use of pyridine‐4‐thiol (PT) to preserve certain aryl bromides in strong alkali is reported ( Scheme 1 ). The presence of this additive or of some of its amphoteric analogs such as 3‐hydroxypyridin‐4(1 H )‐ones suppresses the replacement of the Br‐substituent by hydroxide and alkoxide ions. A mechanistic interpretation of the effect is proposed.