Polarographic study of aliphatic nitro compounds

Conclusions Study bas shown that the first stage in the reduction of 1,1-dinitroethane and fluorodinitromethane in strongly acidic solution is a two-electron C-N bond rupture process, the subsequent stages of the reaction being determined by the relative rates of the competing processes of protonation, nitrosation, and Neff reaction.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 567–573, March, 1977.     

Polarographic study of aliphatic nitro compounds

Conclusions In polarograms of solutions of salts of CH₂(NO₂)₂, CH₃CH(NO₂)₂, FCH(NO₂)₂, and CH₃CH₂NO₂ in abs. methanol, an anodic wave is present, due to increased ionization of mercury, by the tying up of mercury ions with the anions of these compounds to form slightly dissociated organomercury compounds.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2021–2023, September, 1980.     

Electrolysis of aliphatic nitro compounds

Conclusions Data on electrolysis in strongly acidic media have shown that, contrary to accepted belief, reduction of the un-ionized form of trinitromethane proceeds through C-N bond rupture rather than through breakage of the nitro group N-O bond.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1725–1729, August, 1976.     

New reaction of aliphatic nitro compounds

Conclusions Primary aliphatic nitro compounds react with magnesyl derivatives of tert-butylamine with the formation of the corresponding amidooximes, while 2-nitropropane under analogous conditions gives a -aminooxime.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2873–2874, December, 1988.     

Denitrohydrogenation of aliphatic nitro compounds and a new use of aliphatic nitro compounds as radical precursors

Aliphatic nitro groups are replaced by hydrogen on treatment with tributyltin hydride which proceeds via free radical chain processes. As the nitro group is selectively denitrated and other reducible groups are not affected with tributyltin hydride, this reaction can be used as a method for removing the nitro group from polyfunctional compounds. The radical intermediates generated via denitration can be also used for the carbon-carbon bond forming reactions.     

Chemical ionization of aliphatic nitro compounds

The chemical ionization mass spectra of various aliphatic nitro compounds have been studied. Almost all the nitro compounds form stable [M+H]⁺ ions in sharp contrast to the instability of their ions produced by other ionization techniques. The fragmentations of the [M+H]⁺ ions are discussed, the mechanisms and structures of fragment ions proposed being supported by quantum mechanical calculations. Correlations between chemical ionization mass spectra and structures of compounds studied are outlined. Reliable identification of mono- and polynitroalkanes and some related derivatives may be made by analysis of their chemical ionization mass spectra.     

Relative molecular mass information from aliphatic nitro compounds: A chemical ionization study

The mass spectra of a number of aliphatic nitro compounds have been studied using electron Ionization (EI) and a variety of chemical Ionization (CI) techniques in attempts to obtain relative molecular mass information. The use of positive ion ammonia chemical Ionization techniques gave very satisfactory results, providing abundant [M + NH4]⁺ ions, not only from both primary and secondary nitro compounds, but also from the much more labile tertiary nitro compounds. However, the use of methane and isobutane positive ion CI or EI conditions resulted in facile fragmentation with little relative molecular mass information being made available. Negative ion CI using methane, isobutane or ammonia as moderating gases all gave abundant [M ? 1]^? ions with primary and secondary nitro compounds but at much reduced sensitivity.