Abstract
First-wave oxidation of vicinal dioximes corresponds to the transfer of two electrons and two protons to give furoxans, which are further oxidized at the potentials of the second wave. It is shown that the key step in the electrochemical cyclization of vicinal dioximes is oxidation of the intermediate iminoxyl radicals to oxoimmonium cations, which react with the adjacent oxime group.
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J. Tabacovič, M. Trkovnik, and D. Galijas, J. Electroanal. Chem.,86, 241 (1978).
N. Henning, T. Dassler, and W. Jugelt, Z. Chem.,22, No. 1, 25 (1982).
W. Jugelt, M. Tismer, and M. Rauh, Z. Chem.,23, No. 1, 29 (1983).
V. A. Petrosyan, M. E. Niyazymbetov, and é. V. Kozlovskaya, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1691 (1986).
V. A. Petrosyan, M. E. Niyazymbetov, and é. V. Ul'yanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1683 (1989).
V. A. Petrosyan, M. E. Niyazymbetov, and é. V. Ul'yanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1687 (1989).
V. A. Petrosyan, M. E. Niyazymbetov, and é. V. Ul'yanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 625 (1990).
L. N. Nekrasov, Polarography. Problems and Prospects [in Russian], Ya. P. Stradynya and S. T. Mairanovskii (eds.), Zinatne, Riga (1977), pp. 350–372.
H. E. Ungnade and L. W. Kissinger, Tetrahedron,19, Suppl. 1, 143 (1963).
L. I. Khmel'nitskii, S. S. Novikov, and T. I. Godovikova, The Chemistry of Furoxans. Structure and Synthesis [in Russian], Nauka, Moscow (1981), pp. 216–249.
R. Stosser, W. Jugelt, T. Dassler, and B. Britze, Z. Chem.,24, No. 2, 66 (1984).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 630–634, March, 1990.
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Niyazymbetov, M.E., Ul'yanova, é.V. & Petrosyan, V.A. Electrochemical oxidation of vicinal dioximes. Russ Chem Bull 39, 551–554 (1990). https://doi.org/10.1007/BF00959581
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DOI: https://doi.org/10.1007/BF00959581