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Vicarious Nucleophilic Substitution of Hydrogen in Nitropyridines by α-Chloroalkyl Phenyl Sulfone Carbanions

✍ Scribed by M??kosza, Mieczystaw ;Chylińska, Barbara ;Mudryk, Bogustaw

Publisher: John Wiley and Sons
Year: 1984
Tongue: English
Weight: 391 KB
Volume: 1984
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198419840103

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✦ Synopsis

Abstract

Nitropyridines and chloronitropyridines react with carbanions of α‐chloroalkyl phenyl sulfones yielding products of the vicarious nucleophilic substitution of hydrogen at positions ortho and para to the nitro group. A general rule that the vicarious substitution of hydrogen proceeds faster than the nucleophilic substitution of equally activated halogen is observed. The orientation of the hydrogen substitution is discussed.

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