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Chem Pharm Bull (Tokyo). 2013;61(10):1065-70. Epub 2013 Aug 3.

Formation mechanism of triketo cage compounds from reaction of phencyclone with benzoquinones: cascade reaction of intermolecular [4+2]π and intramolecular [2+2]π cycloadditions.

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  • 1Faculty of Pharmaceutical Sciences, Sojo University.


The [4+2]π cycloadduct (3aa) of phencyclone (1a) and benzoquinone (2a) readily transformed into the corresponding [2+2]π cycloadduct (4aa) during purification. The structure of the triketo cage compound was determined by single crystal X-ray analysis. The structure-reactivity relationships are discussed based on the PM6-calculated energy profiles for the whole photocycloaddition of the [4+2]π cycloadducts of some cyclopentadienones and benzoquinones.

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