Formation of the 5??Azoniafulvene Ion and its Benzo??annellated Analogue from N??Mannich Bases of Pyrrole and Indole

…, AO Bringhen, PJ Wirthner, JC Schärer

Index: Burger, Ulrich; Bringhen, Alain O.; Wirthner, Philippe J.; Schaerer, Jean-Claude Helvetica Chimica Acta, 1985 , vol. 68, p. 2275 - 2281

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Citation Number: 9

Abstract

Abstract 1-Dialkylaminomethylpyrroles are shown to behave in many respects like aminals. Acylation by an acid chloride, for instance, occurs normally at the amine-type N-atom rather than at the pyrrole ring. Spontaneous cleavage of the resulting quaternary acylammonium salts affords the 5-azoniafulvene ion (3). This higly reactive iminium ion, and its benzo- annellated analogue (4) can be trapped by electron rich aromatic compounds such as N- ...