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Communication | Special issue | Vol 5, No. 1, 1976, pp.147-151
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0147
The Reactions of Carbonyl Ylides with Azodicarboxylic Esters

Helmut Hamberger, Rolf Huisgen,* Volker Markowski, and Scarlett Sustmann

*Institut für Organische Chemie, Universität München, Karlstrasse 23, D-80333 München, Germany


The carbonyl ylides, generated by thermal electrocyclic ring opening of 2,3-diaryl-2,3-dicyanooxiranes, combine with azodicarboxylic esters to give primary cycloadducts which eliminate aroyl cyanide and produce α-cyanoarylidenehydrazine-Nβ,Nβ-dicarboxylic esters. Whereas the dimethyl esters are thermostable, the diethyl esters undergo a fragrmentation to ethyl α-cyanoarylidenehydrazine-Nβ-carboxylate besides ethylene and carbon dioxide.