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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Abstract
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 |
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| 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 |
| URI: | http://repo.dma.dp.ua/id/eprint/5341 |
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