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Synthesis, structures, and properties of new sterically hindered hydrazine-based catecholaldimines

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Abstract

New sterically hindered catecholaldimines derived from hydrazine were synthesized in high yields. Two procedures for the synthesis of sterically hindered catecholaldimines were developed: by the reaction of 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde with hydrazines (hydrazine hydrate, phenyl-, 1,1-diphenyl-, and (diphenylmethylene)hydrazines, acetyl and benzoyl hydrazides) or by the reaction of 3,5-di-tert-butyl-6-(hydrazonomethyl)catechol with a carbonyl compound (the reaction with 4-N,N-dimethylaminobenzaldehyde). The X-ray diffraction analysis and IR, UV, and NMR spectroscopic studies showed that these compounds exist in the catecholic form both in solution and the crystalline state.

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, Nizhny Novgorod, 603137, Russian Federation

    M. V. Arsenyev, N. M. Khamaletdinova, E. V. Baranov, S. A. Chesnokov & V. K. Cherkasov

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  1. M. V. Arsenyev
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  2. N. M. Khamaletdinova
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  3. E. V. Baranov
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  4. S. A. Chesnokov
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  5. V. K. Cherkasov
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Correspondence to M. V. Arsenyev.

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Based on the materials of the International Conference “Organometallic and Coordination Chemistry: Achievements and Challenges” (VI Razuvaev Lectures; September 18–23, 2015, Nizhny Novgorod).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1805–1813, July, 2016.

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Arsenyev, M.V., Khamaletdinova, N.M., Baranov, E.V. et al. Synthesis, structures, and properties of new sterically hindered hydrazine-based catecholaldimines. Russ Chem Bull 65, 1805–1813 (2016). https://doi.org/10.1007/s11172-016-1514-9

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  • DOI: https://doi.org/10.1007/s11172-016-1514-9

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