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Abstract
AbstractWhen 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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