Pyridine‐4‐thiol and Amphoteric Analogs: Novel Protection of Aryl Bromides in Strong Alkali | Zendy

Chen WeiMin | Zendy; Cheng Chao | Zendy; Li BingZhou | Zendy; Ho TseLok | Zendy; Cai ZhaoShuo | Zendy; Wang Yuqiang | Zendy; Sun PingHua | Zendy

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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.

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