Reaction of 2,4,6-Tri-t-butylnitrobenzene with Alky Grignard Reagents
- 1 December 1975
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 48 (12) , 3727-3732
- https://doi.org/10.1246/bcsj.48.3727
Abstract
Reactions of 2,4,6-tri-t-butylnitrobenzene (1) with alkylmagnesium halides afforded 2,4,6-tri-t-butylaniline (2), N-alkyl-2,4,6-tri-t-butylanilines (3), 6-alkyl-2,4-di-t-butylanilines (4), 4-alkyl-1-hydroxyimino-2,4,6-tri-t-butyl 2,5-cyclohexadienes (5), and 6-alkyl-1-hydroxyimino-2,4,6-tri-t-butyl-2,4-cyclohexadienes (6) depending on the Grignard reagents used. Reduction of the oxime 6 proved to be responsible for the formation of the aniline 4. Comparison of the present reactions with those of 2,4,6-tri-t-butylnitrosobenzene (7) with Grignard reagent, syn-anti-isomzrs of the oxime 6, and the formation mechanisms of the products have been discussed.Keywords
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