Abstract

Addition of the cyanomethyl anion to the triple bond of the cyano group in 2-cyano-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl with the formation of stable (Z)-3-amino-3-(4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl-2-yl)acrylonitrile is reported. The product yield was dependent on the cyanomethyl anion salt counter-ion and was highest in the case of the potassium salt in liquid ammonia. Crystallization provided at least two polymorphs of the synthesized nitroxide according to single crystal X-ray data. ESR spectroscopy revealed delocalization of unpaired electron spin density into the enaminonitrile substituent. The synthesized nitronyl nitroxide is of interest for the preparation of new polyfunctional nitroxides and as polydentate paramagnetic ligands.

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