Application of the intramolecular aza-Wittig reaction to the synthesis of vinylogous urethanes and amides

PH Lambert, M Vaultier, R Carrié

Index: Lambert, P. H.; Vaultier, M.; Carrie, R. Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5352 - 5356

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Citation Number: 68

Abstract

The treatment of o-azido P-dicarbonyl derivatives with 1 equiv of triphenylphosphine leads to a transient phosphinimine (Staudinger reaction), which cyclizes into vinylogous urethanes and amides via an intramolecular am-Wittig reaction in excellent yields. The starting azides were obtained by a nucleophilic substitution by NaN3 in MezSO on the corresponding w- halo 8-dicarbonyl derivatives that were accessible by the y-alkylation of P-dicarbonyl ...