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Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2006, Number: 21, Pages: 4861-4866 Pages count : 6 DOI: 10.1002/ejoc.200600486
Tags Density functional calculations, Electrophilic reactions, Imides, Superacids, Superelectrophilic activation
Authors Koltunov Konstantin Yu. 1,2 , Prakash G.K.Surya 1 , Rasul Golam 1 , Olah George A. 1
Affiliations
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

Funding (1)

1 National Science Foundation

Abstract: 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.
Cite: 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 ANCAN OpenAlex
Dates:
Submitted: Jun 6, 2006
Published online: Sep 4, 2006
Published print: Oct 27, 2006
Identifiers:
Web of science: WOS:000241909200012
Scopus: 2-s2.0-33750871283
Elibrary: 13517913
Chemical Abstracts: 2006:1221352
Chemical Abstracts (print): 146:121786
OpenAlex: W2075722129
Citing:
DB Citing
Web of science 34
Scopus 33
Elibrary 34
OpenAlex 36
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