Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

The formation of nitriles by pyrolysis of N-substituted chloroacetamides

RFC Brown, M Butcher and RA Fergie

Australian Journal of Chemistry 26(6) 1319 - 1326
Published: 1973


Pyrolysis of chloroacetamides RNHCOCH2Cl at 780-850°C/0.1-0.4 mm with short contact time gives nitriles RCN in 45-60% yield (R = phenyl, o- tolyl, p-tolyl, benzyl, or cyclohexyl). A mechanism is proposed involving the formation of the iso-nitrile RNC, formaldehyde, and hydrogen chloride. N-Chloroacetylbiphenyl-2-amine gives biphenyl-2- carbonitrile (45%) and phenanthridine (15%).

© CSIRO 1973

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