Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 1, Pages 351-356Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8077076
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Funding
- National Science Foundation [CHE-0449478]
- Georgia Cancer Coalition
- ACS Petroleum Research Fund [434444-AC4]
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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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