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Difluorodiazirine. V. difluoromethyl esters and ethers
Author(s) -
Mitsch Ronald A.,
Robertson Jerry E.
Publication year - 1965
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.5570020209
Subject(s) - chemistry , aniline , benzamide , methanol , organic chemistry , nucleophilic substitution , nucleophile , ammonium hydroxide , medicinal chemistry , fluorine , catalysis
The preparation of difluoromethyl esters and ethers by the photolytic reaction of difluorodiazirine with acids and alcohols, respectively, is described. Difluoromethyl benzoate is converted, under mild conditions, to methyl benzoate, benzamide and benzanilide by reaction with methanol, ammonium hydroxide and aniline, respectively. The difluoromethyl esters are activated to nucleophilic reaction by virtue of the α‐fluorine substitution.