New sterically hindered di-o-quinones of the biphenyl series |
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Authors: | G. A. Abakumov V. I. Nevodchikov N. O. Druzhkov L. N. Zakharov L. G. Abakumova Yu. A. Kurskii V. K. Cherkasov |
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Affiliation: | (1) G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603600 Nizhnii Novgorod, Russian Federation |
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Abstract: | New di-o-quinones of the biphenyl series, namely, 2,2′-dialkyl-5,5′-di-tert-butylbiphenyl-3,4,3′,4′-diquinones, were synthesized. Their structures were established by IR and NMR spectroscopy. The molecular structure of 2,2′-dimethyl-5,5′-di-tert-butylbiphenyl-3,4,3′,4′-diquinone was established by X-ray structural analysis. The structure is characterized by orthogonal (the torsion angle is 82.9°) mutual arrangement ofo-benzoquinone fragments. ESR studies demonstrated that chemical reduction of diquinone proceeds in four oneelectron stages to form paramagnetic mono- and trianions as intermediates. Quinopyrocatechols, which are intermediates in the synthesis of di-o-quinones, were isolated and characterized. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 4, pp. 804–809, April, 1997. |
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Keywords: | synthesis di-o-quinones structure IR spectroscopy NMR, X-ray structural analysis |
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