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Transformations of arylcyclopropanes under the action of dinitrogen tetroxideстатья
Информация о цитировании статьи получена из
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 28 мая 2015 г.
- Авторы: Mochalov S.S., Kuz’min Ya I., Fedotov A.N., Trofimova E.V., Gazzaeva R.A., Shabarov Yu S., Zefirov N.S.
- Журнал: Russian Journal of Organic Chemistry
- Том: 34
- Номер: 9
- Год издания: 1998
- Издательство: Maik Nauka/Interperiodica Publishing
- Местоположение издательства: Russian Federation
- Первая страница: 1322
- Последняя страница: 1330
- Аннотация: p-Bromophenylcyclopropane, 1- and 2-methylphenylcyclopropanes, and 1,2-di-p-tolyl- and l,2-bis(p-methoxyphenyl)cyclopropanes react with N2O4with opening of the three-membered ring. Reactions of p-methoxyphenylcyclopropane, 6-cyclopropyl-l,4-benzodioxane, and 2-cyclopropylfluorene yield the corresponding nitroaromatic derivatives with conservation of the cyclopropane ring. The nitration of p-methoxyphenylcyclopropane is accompanied by demethylation. 2-Nitro- and 4-nitrophenylcyclopropanes, as well as l-chloro-2-phenylcyclopropane, do not react with N2O4 under the same conditions. The differences in the behavior of arylcyclopropanes in reactions with N2O4 are explained by the different action of nitrosonium ion in the first reaction step: It acts as either electrophilic species capable of initiating opening of the cyclopropane ring or one-electron oxidant converting the initial arylcyclopropanes into the corresponding radical cations which are precursors of Wheland σ complexes responsible for aromatic nitration. copy;1998 MAHK "Hayka/Interperiodica".
- Добавил в систему: Зефиров Николай Серафимович