Synthesis and reactions of highly electrophilic imines containing the N-cyano group

M Ramezanian, AB Padias, FD Saeva…

Index: Ramezanian, Merrikh; Padias, Anne Buyle; Saeva, F. D.; Hall, H. K. Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1768 - 1771

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Citation Number: 7

Abstract

Toluene solutions of tricyanomethanimine, 1, and methyl 3-aza-2, 3-dicyanoacrylate, 2, were synthesized by thermal decomposition of, respectively, 2, 2-diazido-l, 1-dicyanoethylene and methyl 3, 3-diazido-Z-cyanoacrylate. Diethyl (cyanoimino) malonate, 3, was obtained from the reaction of diethyl ketomalonate with bis (trimethy1-sily1) carbodiimide. None of these electrophilic imines could be isolated, because oligomerization occurred in every case. ...