Conclusions
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1.
We have developed a convenient preparative method for obtaining nitroxide radicals by oxidation of di-tert-alkylhydroxylamines and their salts by nitrous acid.
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2.
We propose protection of the nitride functional group by conversion of the nitroxide radical to the salt of the hydroxylamine, and removal of the protection by oxidation with nitrous acid.
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Literature cited
A. K. Hoffman and A. T. Henderson, J. Am. Chem. Soc.,83, 4671 (1961).
É. G. Rozantsev and V. A. Golubev, Izv. Akad. Nauk SSSR, Ser. Khim., 891 (1966).
O. Piloty and B. Schwerin, Chem. Ber.,34, 1870 (1901).
V. A. Golubev, É. G. Rozantsev, and M. B. Neiman, Izv. Akad. Nauk SSSR, Ser. Khim., 1927 (1965).
L. B. Volodarskii and G. A. Kutikova, Izv. Akad. Nauk SSSR, Ser. Khim., 937 (1971).
T. Toda, E. Mory, and K. Murayama, Bull. Chem. Soc. Jpn.,45, 1904 (1972).
É. G. Rozantsev, Free Imino Oxide Radicals [in Russian], Khimiya, Moscow (1970).
L. A. Krinitskaya and L. B. Volodarskii, Izv. Akad. Nauk SSSR, Ser. Khim., 443 (1982).
J. Cella, J. Kelly, and E. Kenehan, J. Am. Chem. Soc.,89, 3055 (1967).
L. F. Fieser and M. Peters, J. Am. Chem. Soc.,53, 4080 (1931).
L. A. Krinitskaya, É. G. Rozantsev, and M. B. Neiman, Izv. Akad. Nauk SSSR, Ser. Khim., 115 (1965).
V. A. Golubev and L. A. Krinitskaya, USSR Pat. No. 929,633, 23.05.1982. Published in B.I. (1982), No. 19.
V. A. Golubev, G. I. Voronina, and É. G. Rozantsev, Izv. Nauk SSSR, Ser. Khim., 2605 (1970).
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Translated from Izvestiya Akademiya Nauk SSSR, Seriya Khimiya, No. 2, pp. 391–394, February, 1983.
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Krinitskaya, L.A., Volodarskii, L.B. Oxidation of di-tert-alkylhydroxylamines to nitroxide radicals by nitrous acid. Russ Chem Bull 32, 352–355 (1983). https://doi.org/10.1007/BF00957948
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DOI: https://doi.org/10.1007/BF00957948