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Communication | Special issue | Vol 10, No. 1, 1978, pp.199-205
Published online, 1st January, 1970
DOI: 10.3987/S-1978-01-0199
Synthesis and Reactivity of Heterocyclic α-Diazo Carbonyl Compounds

Axel Schmitz, Udo Kraatz, and Friedhelm Korte*

*Institut für Organische Chemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany

Abstract

Synthesis of α-diazo substituted 3-carboxylic esters of isoxazolone and pyrazolone (3a,b) by diazo group transfer succeeds only with the use of the azidinium salt 2.
The thermodynamically quite stable diazo compounds 3a, b are very resistant to mineral acids but can be readily coupled to form azo derivatives with compounds containing an active C-H bond. Hydrolysis of their labile phosphazines 6a, and b readily gives the hydrazones 7a,b.