1-Aza-1-propyne1-oxide

Definition

ChEBI: The nitrile oxide resulting from the oxidation of the nitrogen atom of acetonitrile.

Synthesis

1-Aza-1-propyne1-oxide is most commonly generated in situ from Nitroethane by treatment with Phenyl Isocyanate/Triethylamine at rt (the Mukiayama method). Other reagents (AcCl, Ac2O, or POCl3) may be used in place of PhNCO. Acetonitrile oxide may be generated by flash vacuum pyrolysis (FVP) of 3,4-dimethylfuroxan, by hypochlorite oxidation of acetaldehyde oxime,4b or from acetohydroxamoyl chloride.