Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes
Publication type: Journal Article
Publication date: 2006-11-01
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
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Koltunov K. Yu. et al. Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes // European Journal of Organic Chemistry. 2006. Vol. 2006. No. 21. pp. 4861-4866.
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Koltunov K. Yu., Vijaya Prakash G., Rasul G., Olah G. Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes // European Journal of Organic Chemistry. 2006. Vol. 2006. No. 21. pp. 4861-4866.
Cite this
RIS
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TY - JOUR
DO - 10.1002/ejoc.200600486
UR - https://doi.org/10.1002/ejoc.200600486
TI - Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes
T2 - European Journal of Organic Chemistry
AU - Koltunov, Konstantin Yu
AU - Vijaya Prakash, G.
AU - Rasul, Golam
AU - Olah, George
PY - 2006
DA - 2006/11/01
PB - Wiley
SP - 4861-4866
IS - 21
VL - 2006
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
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@article{2006_Koltunov,
author = {Konstantin Yu Koltunov and G. Vijaya Prakash and Golam Rasul and George Olah},
title = {Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes},
journal = {European Journal of Organic Chemistry},
year = {2006},
volume = {2006},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/ejoc.200600486},
number = {21},
pages = {4861--4866},
doi = {10.1002/ejoc.200600486}
}
Cite this
MLA
Copy
Koltunov, Konstantin Yu., et al. “Superacidic Activation of Maleimide and Phthalimide and Their Reactions with Cyclohexane and Arenes.” European Journal of Organic Chemistry, vol. 2006, no. 21, Nov. 2006, pp. 4861-4866. https://doi.org/10.1002/ejoc.200600486.