The articles in this series have been published in five volumes by Verlag Chemie, Weinheim/Bergstrasse. An English edition has also been published. The present article, together with procedures will appear in Volume VI of the series.
Article first published online: 17 DEC 2003
Copyright © 1967 by Verlag Chemie, GmbH, Germany
Angewandte Chemie International Edition in English
Volume 6, Issue 9, pages 733–749, September 1967
How to Cite
Regitz, M. (1967), New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups. Angew. Chem. Int. Ed. Engl., 6: 733–749. doi: 10.1002/anie.196707331
XIIIth report on reactions of compounds containing active methylene groups with azides. From the Habilitation Thesis of M. Regitz, Universität des Saarlandes, Saarbrücken, 1965; supplemented by more recent work.
- Issue published online: 17 DEC 2003
- Article first published online: 17 DEC 2003
- Manuscript Revised: 9 JUN 1967
- Manuscript Received: 29 SEP 1966
- Diazo group transfer;
- Diazo compounds;
- Synthetic methods
When an arenesulfonyl azide, particularly p-toluenesulfonyl azide, reacts, in the presence of a base, with a compound containing an active methylene group, the two hydrogen atoms of the active methylene group are replaced by a diazo group to form a diazo compound and an arenesulfonamide. The method may be used for the synthesis of the diazo derivatives of cyclopentadienes, cyclohexadienes, 1,3-dicarbonyl, 1,3-disulfonyl, and 1,3-ketosulfonyl compounds, ketones, carbonic acid esters, and β-iminoketones. Secondary reactions can lead to azo compounds and heterocycles such as 1,2,3-triazoles, 1,2,3-thiadiazoles, and pyrazolin-4-ones. Azidinium salts react in the same way, but in this case an acidic reaction medium is necessary, a fact that is sometimes advantageous.