Abstract
In the interaction of N-dialkylanilines with benzoyl peroxide there is a transfer of one electron with the formation of the corresponding radical cations. Radical cations of N,N-tetraalkylbenzidines are formed as secondary conversion products of the radical cations of N-dialkylanilines, which exhibit paramagnetic properties.
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B. A. Dolgoplosk and E. I. Tinyakova, Redox Systems as a Source of Free Radicals [in Russian], Nauka, Moscow (1972).
E. D. Vilyanskaya, K. I. Ivanov, and A. V. Koryakin, “Products of the reaction of aromatic amines with hydroperoxides of hydrocarbons,” In: Advances in the Chemistry of Organic Peroxide Compounds and Autooxidation [in Russian], Khimiya, Moscow (1969), pp. 261–265.
D. G. Pobedimskii, A. L. Buchachenko, and M. B. Neiman, “Mechanism of the reactions of peroxides with aromatic amines,” Zh. Fiz. Khim.,42, No. 6, 1436–1440 (1968).
E. T. Seo, F. R. Nelson, I. M. Fritsch et al., “Anodic oxidation pathways of aromatic amines. Electrochemical and EPR studies,” J. Am. Chem. Soc.,88, No. 15, 3498–3503 (1966).
W. M. Fox and W. A. Waters, “The electron spin resonance spectra of some arylammonium radical cations,” J. Chem. Soc., No. 2, 6010–6011 (1964).
L. Horner and H. Junkermann, “Studien zum Ablauf der Substitution. 7. Beitrag zum kinetischen Nachweis von Durchgangsradikalen in System: tertiares Amin — Dibenzoylperoxyd,” Ann. Chem.,591, No. 1/2, 53–68 (1955).
I. M. Fritsch and R. N. Adams, “Reinterpretation of the EPR spectrum of N,N-tetramethylbenzidine cation,” J. Chem. Phys.,43, No. 6, 1887–1889 (1965).
F. A. Bell, Ph. Beresford, L. I. Kricka. and A. Ledwith, “Cation radicals, Reactions of cation radical form substrates containing a p-dimethylaminophenyl group,” J. Chem. Soc. Perkin Trans. I, No. 15, 1788–1792 (1974).
K. B. Yatsimirskii, B. G. Zhelazkova, and N. D. Iordanov, “Free radicals from N-substituted anilines in redox reactions,” Dokl. Akad. Nauk. SSSR,233, No. 4, 646–648 (1977).
F. T. Naylor and B. C. Saunders, “Studies in peroxidase,” J. Chem. Soc., No. 1, 3519–3523 (1950).
J. Wertz and J. Bolton, Electron Spin Resonance. Elementary Theory and Practical Applications, McGraw-Hill (1972).
G. A. Razuvaev, L. M. German, L. N. Mikhotova, and D. M. Yanovskii, “Radical reactions of organic peroxydicarbonates. Interaction of dicyclohexylperoxydicarbonate with dimethylaniline,” Zh. Org. Khim.,1, No. 61, 79–82 (1965).
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Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 21, No. 5, pp. 623–626, September–October, 1985.
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Titov, E.V., Alaev, Y.N. & Luk'yanenko, L.V. Mechanism of the oxidation of certain n-dialkylanilines by benzoyl peroxide. Theor Exp Chem 21, 596–599 (1985). https://doi.org/10.1007/BF00944102
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DOI: https://doi.org/10.1007/BF00944102