Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes Научная публикация
Журнал |
European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690 |
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Вых. Данные | Год: 2006, Номер: 21, Страницы: 4861-4866 Страниц : 6 DOI: 10.1002/ejoc.200600486 | ||||
Ключевые слова | Density functional calculations, Electrophilic reactions, Imides, Superacids, Superelectrophilic activation | ||||
Авторы |
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Организации |
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Информация о финансировании (1)
1 | National Science Foundation |
Реферат:
When activated in the CF3SO3H/SbF5 acid system maleimide (1) and phthalimide (2) undergo selective ionic hydrogenation with cyclohexane to give 1,5-dihydropyrrol-2-one (3) and phthalimidine (11), respectively. When treated with aluminum halides, N-phenylmaleimide (4) reacts with cyclohexane to give N-phenylsuccinimide (5), whereas 2 still gives 11. Imide 1 also condenses with benzene in trifluoromethanesulfonic acid (CF3SO3H) to give 1,5-dihydro-5,5-diphenylpyrrol-2-one (7) as the major product. However, in the presence of aluminum halides 1 reacts with benzene, toluene, and o-dichlorobenzene to give 3-arylsuccinimides 8–10, respectively. Imide 2 reacts with benzene under the influence of trifluoromethanesulfonic acid as well as aluminum halides to yield 3,3-diphenylphthalimidine (12). The mechanism of these reactions, with potential involvement of superelectrophilic dicationic intermediates, is discussed.
Библиографическая ссылка:
Koltunov K.Y.
, Prakash G.K.S.
, Rasul G.
, Olah G.A.
Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes
European Journal of Organic Chemistry. 2006. N21. P.4861-4866. DOI: 10.1002/ejoc.200600486 WOS Scopus РИНЦ
Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes
European Journal of Organic Chemistry. 2006. N21. P.4861-4866. DOI: 10.1002/ejoc.200600486 WOS Scopus РИНЦ
Даты:
Поступила в редакцию: | 6 июн. 2006 г. |
Опубликована online: | 4 сент. 2006 г. |
Опубликована в печати: | 27 окт. 2006 г. |
Идентификаторы БД:
Web of science | WOS:000241909200012 |
Scopus | 2-s2.0-33750871283 |
РИНЦ | 13517913 |
Chemical Abstracts | 2006:1221352 |
Chemical Abstracts (print) | 146:121786 |
OpenAlex | W2075722129 |