title: Photochemical generation and reversible cycloaromatization of a nine-membered ring cyclic enediyne.
abstract: Irradiation of the nine-membered ring enediyne precursor, which has one of its triple bonds masked as cyclopropenone, efficiently (Phi = 0.34) generates the reactive 4,5-benzocyclonona-2,6-diynol. The latter rapidly equilibrates with the corresponding 1,4-didehydronaphthalene diradical and then undergoes rate-limiting hydrogen abstraction to produce the ultimate product of the Bergman cyclization, benz[f]indanol.
authors.affiliation: Department of Chemistry, University of Georgia, Athens, Georgia 30677, USA.
authors.forename: Dinesh R
authors.initials: DR
authors.lastname: Pandithavidana
authors.forename: Andrei
authors.initials: A
authors.lastname: Poloukhtine
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Popik
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D004278:DNA, Superhelical / Q000737:chemistry; D003851:Deoxyribonucleases / Q000737:chemistry; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D055668:Photochemical Processes; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics
chemical_list: D000480:Alkynes; D003521:Cyclopropanes; D004278:DNA, Superhelical; D007189:Indans; D009281:Naphthalenes; C120343:cyclopropenone; D003851:Deoxyribonucleases