Abstract
The tri-tert-butoxyaluminum—tert-butyl hydroperoxide system generates molecular oxygen in the electron-excited singlet state (1O2), which oxidizes diphenylamine, N-ethylaniline, aniline, and 2,6-diisopropylaniline to form nitroxyl radicals. The latters were identified by ESR at 240—293 K. Oxidation proceeds via the intermediate formation of nitrogen-containing N-peroxide compounds.
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V. A. Dodonov, L. P. Stepovik, and S. M. Sofronova, Zh. Obshch. Khim., 1990, 60, 1839 [J.Gen. Chem. USSR, 1990, 60 (Engl. Transl.)].
V. A. Dodonov and L. P. Stepovik, Zh. Obshch. Khim., 1992, 62, 2630 [Russ. J. Gen. Chem., 1992, 62 (Engl. Transl.)].
D. T. Sawyer, Coord. Chem. Rev., 1997, 165, 297.
V. A. Dodonov, L. P. Stepovik, A. S. Soskova, and E. A. Zaburdaeva, Zh. Obshch. Khim., 1994, 64, 1715 [Russ. J. Gen. Chem.,1994, 64 (Engl. Transl.)].
V. A. Dodonov, E. A. Zaburdaeva, N. V. Dolganova, L. P. Stepovik, and T. I. Zinovêva, Zh. Obshch. Khim., 1997, 67, 988 [Russ. J. Gen. Chem., 1997, 67 (Engl. Transl.)].
L. P. Stepovik, V. A. Dodonov, and E. A. Zaburdaeva, Zh. Obshch. Khim., 1997, 67, 116 [Russ. J. Gen. Chem., 1997, 67 (Engl. Transl.)].
V. A. Dodonov, E. A. Zaburdaeva, and L. P. Stepovik, Zh. Obshch. Khim., 2000, 70, 1577 [Russ. J. Gen. Chem., 2000, 70 (Engl. Transl.)].
E. A. Zaburdaeva, L. P. Stepovik, and V. A. Dodonov, VI Intern. Conf. on Heteroatom Chemistry (Lodz, June 24-28, 2000), Abstrs., Lodz (Poland), 2001, 143.
L. P. Stepovik, I. M. Martynova, V. A. Dodonov, and V. K. Cherkasov, Izv. Akad. Nauk, Ser. Khim., 2002, 590 [Russ. Chem. Bull., Int. Ed., 2002, 51, 638].
S. L. Khursan, V. V. Shereshovets, A. F. Khalizov, A. I. Voloshin, V. D. Komissarov, and V. P. Kazakov, Izv. Akad. Nauk, Ser. khim., 1993, 2056 [Russ. Chem. Bull., 1993, 42, No. 12 (Engl. Transl.)].
S. L. Khursan, A. F. Khalizov, and V. V. Shereshovets, Izv. Akad. Nauk, Ser. Khim., 1997, 924 [Russ. Chem. Bull., 1997, 46, 884 (Engl. Transl.)].
Organic Synthesis. An Annual Publication of Satisfactory Methods for the Preparation of Organic Chemicals, New York, 1940-1945.
L. Gatterman and G. Viland, Prakticheskie raboty po organicheskoi khimii [Practical Works on Organic Chemistry], Goskhimizdat, Moscow, 1948, 516 pp. (in Russian).
V. B. Ivanov, V. Ya. Shlyapintokh, A. B. Shapiro, O. M. Khvostach, and E. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim., 1974, 1916 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1974, 23 (Engl. Transl.)].
J. Pannell, Mol. Phys., 1962, 5, 291.
G. Chappelet-Letourneux, H. Lemaire, and A. Rassat, Bull. Soc. Chim. Fr., 1965, 3283.
R. A. Abramovich and S. R. Challand, J. Chem. Soc., 1972, 16, 964.
S. Terabe and R. Konaka, J. Chem. Soc., Perkin Trans. 2, 1972, 14, 2163.
S. V. Zelentsov, N. V. Zelentsova, A. B. Zhezlov, and A. V. Oleinik, Khim. Vys. Energ., 2000, 34, 201 [High Energy Chem., 2000, 34 (Engl. Transl.)].
C. Lee Go and W. H. Waddell, J. Org. Chem., 1983, 48, 2897.
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Dodonov, V.A., Zaburdaeva, E.A., Stepovik, L.P. et al. Electron-excited dioxygen generated by the tri-tert-butoxyaluminum—tert-butyl hydroperoxide system as an efficient oxidant of aniline and some N-substituted anilines. Russian Chemical Bulletin 52, 910–915 (2003). https://doi.org/10.1023/A:1024452410055
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DOI: https://doi.org/10.1023/A:1024452410055