Abstract
CLAIMS to have isomerized nitrous esters to the corresponding nitro-compounds by heating the vapour at 100–130° 1,2 have not been substantiated by later workers3. It seems probable that this may be due to decomposition of the nitrous ester giving nitric oxide and the alkoxyl free-radical, which then undergoes disproportionation, yielding the corresponding aldehyde and alcohol. By analogy with the sulphinate–sulphone isomerization4, it was considered probable that the nitrite–nitro isomerization would require the formation of the carbonium and nitrite ions, and it seemed likely that this isomeric change would be facilitated by employing an alkyl group which readily forms a carbonium ion, and also by choosing experimental conditions which would tend to suppress free-radical formation and favour ionization.
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References
Keogi and Chowdhuri, J. Chem. Soc., 109, 701 (1916).
Keogi and Chowdhuri, J. Chem. Soc., 111, 899 (1917).
Levy and Rose, Quart. Rev. Chem. Soc., 1, 359 (1947).
Arcus, Balfe and Kenyon, J. Chem. Soc., 485 (1938).
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KENYON, J., THAIN, E. Isomerization of Dianisylcarbinyl Nitrite to Dianisylnitromethane. Nature 165, 400–401 (1950). https://doi.org/10.1038/165400b0
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DOI: https://doi.org/10.1038/165400b0
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