Conclusions
-
1.
During the hydrolysis of nitroimides, the N-NO2 bond generally undergoes splitting, most likely due to the acid catalysis caused by the HNO3 formed. In the absence of acid catalysis the N-SO2 bond is split in the case of the hydrolysis of nitrosaccharin.
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2.
Under the action of alcohols, the nitroimides of aliphatic and aromatic sulfonic acids are split at the N-NO2 bond. In the case of cyclic nitroimides, splitting of the N-CO bond is preferable.
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3.
The enhancement of the steric effect of the substituants in the alcohol as methyl groups are accumulated in it at theα-carbon atom results in splitting of the cyclic nitroimides at the N-NO2 bond.
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4.
The influence of the nature of the solvent on the direction of the alcoholysis of nitrosaccharin has been studied.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2556–2563, November, 1981.
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Kozlova, I.K., Luk'yanov, O.A. & Tartakovskii, V.A. The chemistry of nitroimides. 2. hydrolysis and alcoholysis of nitromides. Russ Chem Bull 30, 2116–2123 (1981). https://doi.org/10.1007/BF01094641
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DOI: https://doi.org/10.1007/BF01094641