title: 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.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Sojo University.
authors.forename: Koki
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Masashi
authors.initials: M
authors.lastname: Eto
authors.forename: Kazunobu
authors.initials: K
authors.lastname: Harano
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D016227:Benzoquinones; D011083:Polycyclic Compounds; C502795:phencyclone; C004532:quinone