Chemical properties of some new quinoneimine derivatives

Murashevych, B. and Nychyk, N. and Toropin, N. and Trush, Y. and Burmistrov, K. (2019) Chemical properties of some new quinoneimine derivatives. Voprosy khimii i khimicheskoi tekhnologii = Вопросы химии и химической технологии, No. 4. pp. 101-108. ISSN 2413-7987 (Online), ISSN 0321-4095 (Print)


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Ukrainian State University of Chemical Technology, Dnipro, Ukraine The reactions between some C8-substituted quinonearenalazines (their chloro- and aminoderivatives) and hydrogen chloride were investigated. It is shown that in the case of chloroderivatives these reactions lead to the formation of the aromatic 1,4- and 6,3-addition products mixture, regardless of the used solvent. The ratio between these isomers depends on the oxidation-reduction potential of initial quinoneimine. An increase in the acceptor properties of the substitute in the aromatic ring of substrate results in an increase in the content of 1,4-addition product. The addition products are quinogenic and can be oxidized to the corresponding quinoid forms. The last mentioned compounds exist only in antiform in the case of 6,3-addition of hydrogen chloride, while oxidized 1,4-addition products are the mixture of syn- and anti-isomers, which convincingly follows from the NMR spectra of these compounds. Amino-derivatives of quinonearenalazines do not react neither with hydrogen chloride nor with amines, perhaps, due to a considerable decrease in electron deficiency of quinoid cycle under the influence of entered aminogroup. B. Murashevych, N. Nychyk, N. Toropin, Y. Trush, K. Burmistrov

Item Type: Article
Additional Information: DOI: 10.32434/0321-4095-2019-125-4-101-108
Uncontrolled Keywords: quinoneimine, quinonearenalazine, addition, regioselectivity, oxidation-reduction potential, hydrogen chloride.
Subjects: Organic Chemistry
Divisions: Departments > Department of Biochemistry and medical chemistry
Depositing User: Елена Шрамко
Date Deposited: 13 May 2020 11:31
Last Modified: 13 May 2020 11:31

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