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Photochemical Generation and Reversible Cycloaromatization of a Nine-Membered Ring Cyclic Enediyne.

Pandithavidana, D. R.; Poloukhtine, A.; Popik, V. V. Photochemical Generation and Reversible Cycloaromatization of a Nine-Membered Ring Cyclic Enediyne. Journal of the American Chemical Society 2009, 131(1), 351-356.

Abstract

Irradn. of the nine-membered ring enediyne precursor, which has one of its triple bonds masked as cyclopropenone, efficiently (Φ = 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. [on SciFinder(R)]