A New azacyanocarbon, C4N4: tricyanomethanimine

✍ Scribed by H.K. Hall Jr.; M. Ramezanian; F.D. Saeva

• Book ID: 104216465
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 170 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)80264-6

✦ Synopsis

2,2-Dichloroethylene-l,l-dicarbonitrile reacted with sodium azide to give 2,2diazidoethylene-l,l-dicarbonitrile, which underwent thermolysis to give tricyanomethanimine, C4N4. The latter is as reactive as TCNE toward electron-rich molecules.

Although the rich chemistry of the highly electrophilic molecules tetracyanoethylene2 (I) and carbonyl cyanidea (2) has been extensively documented, no report dealing with tricyanomethanimine (3) has appeared in the literature. We now offer a preliminary report on the synthesis and chemistry of this new azacyanocarbon, C4N4.