Transformations of N-Substituted Benzotriazoles into the Corresponding Carbanions by C−Benzotriazole Bond Scission
The Journal of Organic Chemistry1997Vol. 62(12), pp. 4116–4120
Citations Over TimeTop 10% of 1997 papers
Abstract
Various N-substituted benzotriazoles are transformed, by scission of the C-benzotriazole bond, into the corresponding carbanions by treatment with lithium. Thus, N-(diphenylmethyl)benzotriazole (1), N-benzylbenzotriazole (6), and N-allylbenzotriazole (10) all gave carbanions that reacted with diverse electrophiles to afford the corresponding products in good yields. This new methodology was successfully utilized to convert N-benzylbenzotriazole (6) and N-allylbenzotriazole (10) into dianion synthons by a sequential lithiation and reductive coupling and bis(benzotriazolyl)toluene (18) by double reductive couplings, demonstrating the synthetic potential of the present methodology.
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