New Methods of Preparative Organic Chemistry. Transfer of Diazo Groups


  • Doz. Dr. M. Regitz

    Corresponding author
    1. Institut für Organische Chemie der Universitä, 66 Saarbrücken 15 (Germany)
    • Institut für Organische Chemie der Universitä, 66 Saarbrücken 15 (Germany)
    Search for more papers by this author

  • 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.

  • 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.


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.