Abstract
EARLY work1 gives a very confused picture of the reactions which occur in either alkaline or acid hydrolysis of organic esters of nitric acid. The only clearly established point is the occurrence of reactions other than simple fission to alcohol and nitric acid, and the general view was that such side-reactions, including the formation of nitrite, arise from subsequent oxidation of the alcohol by the nitric acid. A more recent study, by Lucas and Hammett2, of the solvolysis of tert.-butyl nitrate revealed the concomitant formation of isobutene, while with benzyl nitrate, benzaldehyde and nitrite are also formed.
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References
Cf., inter alia, Farmer, J. Chem. Soc., 117, 806 (1920); and references cited there.
J. Amer. Chem. Soc., 64, 1928 (1942).
For summarizing papers, cf. Hughes, Trans. Farad. Soc., 37, 603 (1941); Hughes and Ingold, ibid., 657.
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BAKER, J., EASTY, D. Hydrolysis of Organic Nitrates. Nature 166, 156 (1950). https://doi.org/10.1038/166156a0
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DOI: https://doi.org/10.1038/166156a0
