Photochemical Generation and Reversible Cycloaromatization of a Nine-Membered Ring Cyclic Enediyne
Journal of the American Chemical Society2008Vol. 131(1), pp. 351–356
Citations Over TimeTop 10% of 2008 papers
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.
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