Conclusions
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1.
The existence of rigid and labile donor-acceptor complexes in the 2,6-diphenyl-1,4-benzoquinone-ethylenediamine system, the stability of which is determined by the rate of consumption of the 2,6-diphenyl-1,4-benzoquinone, has been demonstrated by means of ESR spectroscopy.
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2.
The fact that cyclohexadienone is formed in the 1,4-addition of ethylenediamine to 2,6-diphenyl-1,4-benzoquinone has been confirmed by NMR spectroscopy.
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3.
The nature of the hydrocarbon fragment of the diamine has a substantial effect on the direction of its reaction with 2,6-diphenyl-1,4-benzoquinone.
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Literature cited
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Saul Patai (editor), The Chemistry of Quinonoid Compounds, Part 1, Hebrew University, Jerusalem, Israel (1974), p. 257.
B. D. Sviridov, M. V. Serdobov, R. V. Poponova, G. A. Nikiforov, K. de Jonge, and V. V. Ershov, Zh. Khim. Fiz., No. 4 (1983).
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A. N. Nesmeyanov and N. A. Nesmeyanov, The Principles of Organic Chemistry, Vol. 2, Khimiya, Moscow (1970), p. 161.
G. O. Bekker (editor), Introduction to the Photochemistry of Organic Compounds [in Russian], Khimiya, Leningrad (1976), p. 168.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, pp. 105–112, January, 1983.
The authors express their thanks to A. K. Ryzhankova for developing a method for the preparation of absolute ethylenediamine.
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Sviridov, B.D., Serdobov, M.V., Porkhun, V.I. et al. Mechanism of the reaction between 2,6-diphenyl-1,4-benzoquinone and alphatic diamines. Russ Chem Bull 32, 88–94 (1983). https://doi.org/10.1007/BF01167766
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DOI: https://doi.org/10.1007/BF01167766