Extended version of a lecture given at the Annual Meeting of the Dechema in Frankfurt/Main on June 14th, 1962, and of the Max Tishler Lecture at Harvard University on December 10th, 1962.
Kinetics and Mechanism of 1,3-Dipolar Cycloadditions†
Article first published online: 17 DEC 2003
Copyright © 1963 by Verlag Chemie, GmbH, Germany
Angewandte Chemie International Edition in English
Volume 2, Issue 11, pages 633–645, November 1963
How to Cite
Huisgen, R. (1963), Kinetics and Mechanism of 1,3-Dipolar Cycloadditions. Angew. Chem. Int. Ed. Engl., 2: 633–645. doi: 10.1002/anie.196306331
- Issue published online: 17 DEC 2003
- Article first published online: 17 DEC 2003
- Manuscript Received: 28 MAR 1963
- Dipolar cycloaddition;
- Reaction mechanisms
Criteria for the mechanism of 1,3-dipolar cycloadditions which lead to 5-membered rings are provided by the stereoselectivity observed with cis-trans isomeric dipolarophiles, by the effect of solvent and substituents on the rate constants, by the activation parameters, and by orientation phenomena. A concerted addition, which can also be described in terms of molecular orbitals and in which the two new σ-bonds are formed simultaneously, although not necessarily at equal rates, offers the best explanation of the experimental facts.