1,3-Dipolar Cycloaddition Reactions of Stable Bicyclic and Monocyclic Azomethine Ylides: Kinetic Aspects

Abstract

Kinetic data for 1,3-dipolar cycloadditions of stable azomethine ylides 1-3 with angle-strained, electron-poor and electron-rich 2 pi-components 4-10 prove that most reactions are LUMOdipole-HOMOdipolarophile-controlled. Small rho-values and a minor solvent effect on the rate constants are in accord with a concerted bond formation in the transition state. (C) 2000 Elsevier Science Ltd. All rights reserved.