
%0 Journal Article
%A Grant, RD 
%A Pinhey, JT 
%A Rizzardo, E 
%A Smith, GC 
%T The Photochemistry of &#945;,&#914;-Unsaturated Nitro Compounds and Nitronic Acids. Concerning Deconjugation and &#945;,&#914;-Unsaturated Ketone Formation
%J Australian Journal of Chemistry
%D 1985/10/01
%V 38
%N 10
%P 1505-1519
%K 
%R https://doi.org/10.1071/CH9851505
%U https://www.publish.csiro.au/paper/CH9851505 
%X The photochemistry of cyclohexylidenenitromethane (6), 3-ethyl-2-nitropent-2-ene (7), (Z)-&#945;-methyl-&#945;- nitrostilbene (12), (E)-3-methyl- 1-nitro-1-phenylbut-1-ene (15) and 4,4-dimethyl-3-nitro-5&#945;-cholest-2- ene (27) has been examined to determine the structural features required for deconjugation to the &#946;, &#947;-unsaturated isomer. The mechanism of the light-induced formation of the corresponding &#945;, &#946;- unsaturated ketone , which may accompany deconjugation , has also been examined. Support for a scheme involving &#947;-hydrogen abstraction to give an unsaturated nitronic acid, followed by N- hydroxyoxaziridine formation and collapse to the ketone, is provided in the photochemistry of the stable nitronic acids, 4-t-butyl-aci-nitrocyclohexane (17) and 9-aci-nitrofluorene (18). Syntheses of the nitro olefins (6), (7), (12), (15) and (27), and the nitronic acid (17) are also reported. 
