Nucleophilic addition to olefins. 4. Structure-reactivity relationships in the reactions of amines with substituted benzylidene Meldrum's acids. Evidence for …

CF Bernasconi, S Fornarini

Index: Bernasconi, Claude F.; Fornarini, Simonetta Journal of the American Chemical Society, 1980 , vol. 102, # 16 p. 5329 - 5336

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Citation Number: 25

Abstract

Abstract: The reactions of piperidine and morpholine with benzylidene Meldrum's acid (1-H) and its p-OMe and p-NMe2 derivatives (1-OMe, 1-NMe,) in water are characterized by a fast and a slow kinetic process. The fast reaction refers to the formation of a zwitterionic adduct (TAi) which is in rapid acid-base equilibrium with TA-(eq 1). The slow process leads, via an iminium ion, to the respective benzaldehyde and Meldrum's acid anion (eq 3) whereby ...