117668-94-7Relevant academic research and scientific papers
Synthesis and Reactions of Highly Electrophilic Imines Containing the N-Cyano Group
Ramezanian, Merrikh,Padias, Anne Buyle,Saeva, F. D.,Hall, H. K.
, p. 1768 - 1771 (1990)
Toluene solutions of tricyanomethanimine, 1, and methyl 3-aza-2,3-dicyanoacrylate, 2, were synthesized by thermal decomposition of, respectively, 2,2-diazido-1,1-dicyanoethylene and methyl 3,3-diazido-2-cyanoacrylate.Diethyl (cyanoimino)malonate, 3, was obtained from the reaction of diethyl ketomalonate with bis(trimethylsilyl)carbodiimide.None of these electrophilic imines could be isolated, because oligomerization occurred in every case.Dilute solutions of 1 and 2 in toluene were stable for several days, so the imines were characterized in solution.Cycloadditionreactions with 2,3-dimethylbutadiene and cyclopentadiene lead to the expected Diels-Alder adducts.With p-methoxystyrene, spontaneous copolymerizations occurred with both 1 and 2.These imines were somewhat less electrophilic than tetracyanoethylene; they behave similarly in cycloaddition reactions, but in contrast they are also able to polymerize.
A NEW AZACYANOCARBON, C4N4: TRICYANOMETHANIMINE
Hall, H. K. Jr.,Ramezanian, M.,Saeva, F. D.
, p. 1235 - 1238 (2007/10/02)
2,2-Dichloroethylene-1,1-dicarbonitrile reacted with sodium azide to give 2,2-diazidoethylene-1,1-dicarbonitrile, which underwent thermolysis to give tricyanomethanimine, C4N4.The latter is as reactive as TCNE toward electron-rich molecules.
