56620-48-5Relevant academic research and scientific papers
The Photochemistry of α,β-Unsaturated Nitro Compounds and Nitronic Acids. Concerning Deconjugation and α,β-Unsaturated Ketone Formation
Grant, Richard D.,Pinhey, John T.,Rizzardo, Ezio,Smith, Geoffrey C.
, p. 1505 - 1519 (2007/10/02)
The photochemistry of cyclohexylidenenitromethane (6), 3-ethyl-2-nitropent-2-ene (7), (Z)-α-methyl-α'-nitrostilbene (12), (E)-3-methyl-1-nitro-1-phenylbut-1-ene (15) and 4,4-dimethyl-3-nitro-5α-cholest-2-ene (27) has been examined to determine the structural features required for deconjugation to the β,γ-unsaturated isomer.The mechanism of the light-induced formation of the corresponding α,β-unsaturated ketone, which may accompany deconjugation, has also been examined.Support for a scheme involving γ-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.
