Bulletin of the Chemical Society of Japan p. 1869 - 1878 (1999)
Update date:2022-08-04
Topics:
Tsutsui, Hironori
Ichikawa, Tomoko
Narasaka, Koichi
Primary amines are prepared by the electrophilic amination of Grignard reagents with benzophenone O-sulfonyloxime derivatives. 4,4'- Bis(trifluoromethyl)benzophenone O-sulfonyloximes react with alkyl Grignard reagents in the presence of a catalytic amount of CuCN in tetrahydrofuran- hexamethylphosphoric triamide to give N-alkylimines, which are readily hydrolyzed to primary amines. 3,3',5,5'-Tetrakis(trifluoromethyl)benzophenone O-p-tolylsulfonyloxime is arylated to the corresponding N-arylimines with aryl Grignard reagents in ether-toluene, and hydrolysis of the resulting imines gives aniline derivatives.
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Doi:10.1002/jlcr.2580120112
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