N -acetonitrile oxide

A typical method for producing in situ acetonitrile N -oxide from nitroethane is treatment with phenyl isocyanate in the presence of triethylamine . Also, acetyl chloride , acetic anhydride or phosphorus oxychloride may be used instead of phenyl isocyanate. Also described are methods for producing vacuum flash pyrolysis from 3,4-dimethylfuroxane and hypochlorite oxidation of acetaloxime . When generating it is necessary to take into account that N -acetonitrile decomposes quickly (within a few minutes at 18 ° C). This occurs mainly by dimerization of 3,4-dimethylfuroxane ^[1] .

N -acetonitrile oxide is soluble in petroleum ether , diethyl ether , benzene , methylene chloride , ethanol , chloroform ; insoluble in cold petroleum ether (–60 ° C) ^[1] .

For N -acetonitrile, NMR spectroscopic data at low temperatures were recorded. In the ¹ H NMR spectrum, a resonance of protons of the methyl group is observed at 2.26 ppm. In the ¹³ С NMR spectrum there are signals of methyl carbon (0.8 ppm) and nitrile (35.6 ppm). ). In the IR spectrum , a band is observed at 2315 cm ^{–1 [1]} .

The main use of N -acetonitrile is its participation in the reactions of dipolar cycloaddition to alkenes . In this case, isoxazolines are formed, which are further converted into the necessary natural compounds or other useful substances. In a similar reaction with alkynes, N -acetonitrile gives isoxazoles ^[1] .

• Bates DK Acetonitrile N-Oxide (Eng.) // Encyclopedia of Reagents for Organic Synthesis. - Wiley, 2001. - DOI : 10.1002 / 047084289X.ra018 .