On the reactivity of triphenylphosphoranylidenesuccinic anhydride with nitrogen nucleophiles: a new synthetic route to nitrogen-containing phosphonium salts

Abstract

As reações do anidrido trifenilfosforanilidenossuccínico frente a aminas, hidrazinas e nucleófilos nitrogenados dipolares foram investigadas, o que levou ao desenvolvimento de um novo método de síntese de sais de fosfônio contendo o fragmento RNHC(C=O)CH 2 CH 2 PPh 3 .The reactions of triphenylphosphoranylidenesuccinic anhydride with amines, hydrazines and dipolar nitrogen nucleophiles were investigated, and a new method of synthesis of phosphonioum salts containing the fragment RNHC(C=O)CH 2 CH 2 PPh 3 is described.

On the Reactivity of α-(Triphenylphosphoranylidene)-benzylphenylketene with Nitrogen Compounds: Synthetic and Mechanistic Implications

“…The results of the present work, together with those obtained previously with triphenylphosphoranylidenesuccinic anhydride, 8 provide an interesting spectrum of reactivity for phosphorus ylides stabilized by electrophilic functions, and also expand the frontiers of applications of cyclopropenone derivatives in synthesis. Particularly, the formation of 17 provides a new route to polysubstituted N-acyl carbamates.…”

“…7 Recently, we reported the study of the reaction of triphenylphosphoranylidenesuccinic anhydride with a broad spectrum of nitrogen nucleophiles and a new method of synthesis of phosphonioum salts was described. 8 Our continued interest in the chemistry of cyclopropenones and their derivatives 1 as well as in the reactivity of phosphorus ylides stabilized by electrophilic functions 8 prompted us to study the behavior of α-TPBPK toward nitrogen compounds. In this work we present our results concerning the reactivity of α-TPBPK with such derivatives with emphasis on synthetic and mechanistic implications.…”