Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes | Sciact - CRIS-система Института катализа

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

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

Koltunov Konstantin Yu. ^1,2 , Prakash G.K.Surya ¹ , Rasul Golam ¹ , Olah George A. ¹

Организации

1	Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, California 90089-1661, USA
2	Boreskov Institute of Catalysis, Pr. Akademika Lavrentieva,5, Novosibirsk, 630090, Russia

Информация о финансировании (1)

National Science Foundation

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.

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 CAPlusCA OpenAlex

Поступила в редакцию:	6 июн. 2006 г.
Опубликована online:	4 сент. 2006 г.
Опубликована в печати:	27 окт. 2006 г.

Web of science:	WOS:000241909200012
Scopus:	2-s2.0-33750871283
РИНЦ:	13517913
Chemical Abstracts:	2006:1221352
Chemical Abstracts (print):	146:121786
OpenAlex:	W2075722129

БД	Цитирований
Web of science	34
Scopus	33
РИНЦ	34
OpenAlex	36