Substitution α to the Nitrogen in Dibenzylamine via Carbanion Intermediates
Open Access
- 1 April 1973
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 51 (7) , 1109-1115
- https://doi.org/10.1139/v73-164
Abstract
A method has been developed for introducing a variety of substituents into the position α to the nitrogen atom of dibenzylamine. Treatment of either the nitroso or the benzoyl derivative of dibenzylamine with lithium diisopropylamide generates a carbanion which reacts with alkyl halides or carbonyl compounds producing α-substitution products in yields of 66–99%. The method also gives good yields of derivatives of N-phenyl-N′-nitroso-piperazine. Attempts to form the carbanion of N-benzoylpiperidine failed.Keywords
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