Divergent behaviour in the isocyanate-induced and thermal generation of nitrile oxides from ethyl nitroacetate

Article abstract of DOI:10.1016/0040-4039(94)88480-3

Ethyl nitroacetate is a source of three nitrile oxides: thermolysis results in elimination of ethanol and carbon dioxide to generate formonitrile oxide (HC≡N⁺-O^-), whereas treatment with phenyl isocyanate and a base gives either ethoxycarbonylformonitrile oxide (EtO₂CC≡N⁺-O^-) or cyanoformanilide N-oxide (PhNHCOC≡N⁺-O^-) depending on the reaction conditions.