Transformations of N-Substituted Benzotriazoles into the Corresponding Carbanions by C−Benzotriazole Bond Scission
摘要:
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.
Dilithium diphenylmethanediide; generation, redox relationship with lithium chlorodiphenylmethanide, implication with regard to aggregation
作者:Nicolaas J. R. van Eikema Hommes、Friedrich Bickelhaupt、Gerhard W. Klumpp
DOI:10.1039/c39910000438
日期:——
Dilithiumdiphenylmethanediide, Ph2CLi2, prepared by reaction of dichlorodiphenylmethane with lithium p,p′-di-tert-butylbiphenyl, reacts with organic halides and carbonyl compounds to give lithiumChlorodiphenylmethanide, Ph2CLiCl, as a major product and is assumed to exist in two different states of aggregation.