Abstract
1,3-Indandione ( 1) readily condenses with benzene and undergoes selective ionic hydrogenation with cyclohexane when activated by superacids, such as CF 3SO 3H, AlCl 3 and AlBr 3 to give 3,3-diphenyl-1-indanone ( 4) and 1-indanone ( 7), respectively. Combination of these reactions in ‘one-pot’ yields 3-phenyl-1-indanone ( 5). In addition, similar reactions have been carried out using the regenerable solid acid, HUSY-zeolite, providing an effective excess of acidic sites. The mechanism of these reactions, with potential involvement of superelectrophilic dicationic intermediates, is discussed.
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