Extended version of lectures given at the Chemists' Meeting in Vienna (Austria) October 1961, and at the Gordon Research Conference, New Hampton (U.S.A.), 1961.
1,3-Dipolar Cycloadditions. Past and Future†
Article first published online: 17 DEC 2003
Copyright © 1963 by Verlag Chemie, GmbH, Germany
Angewandte Chemie International Edition in English
Volume 2, Issue 10, pages 565–598, October 1963
How to Cite
Huisgen, R. (1963), 1,3-Dipolar Cycloadditions. Past and Future. Angew. Chem. Int. Ed. Engl., 2: 565–598. doi: 10.1002/anie.196305651
- Issue published online: 17 DEC 2003
- Article first published online: 17 DEC 2003
- Manuscript Received: 28 MAR 1963
- Dipolar cycloaddition;
In contrast to the very large number of special methods applicable to syntheses in the heterocyclic series, relatively few general methods are available. The 1,3-dipolar addition offers a remarkably wide range of utility in the synthesis of five-membered heterocycles. Here the “1,3-dipole”, which can only be represented by zwitterionic octet resonance structures, combines in a cycloaddition with a multiple bond system – the “dipolarophile” – to form an uncharged five-membered ring. Although numerous individual examples of this reaction were known, some even back in the nineteenth century, fruitful development of this synthetic principle has been achieved only in recent years.