C‐nitroso compounds. Part XIV: Oximes, nitroalkanes and alkyl nitrates by photolysis of C‐nitroso compounds and alkyl nitrites
article
Monomeric primary and secondary nitrosoalkanes have been generated from the trans‐dimers by heating in solution. The monomers are photochemically and thermally far more reactive than the dimers. They are isomerized to oximes in 90% yield thermally. Photolysis of nitrosocyclohexane with red light leads to the oxime in 60% yield. Photolysis in the presence of oxygen gives nitrocyclohexane as the main product (85%), together with a small amount of cyclohexyl nitrate. Considerable amounts of cyclohexanol are formed by oxidation of the solvent cyclohexane, presumably via a nitroxide‐type intermediate. When t‐butyl nitrite is photolyzed with light in the region of 400 nm and in the presence of oxygen in CFCl3, t‐butyl nitrate is produced in 90% yield, by the action of intermediary NO and NO2 radicals. Copyright © 1970 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
TNO Identifier
546153
ISSN
01650513
Source
Recueil des Travaux Chimiques des Pays‐Bas, 89(2), pp. 164-168.
Pages
164-168
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