The Photochemistry of 1-Methoxy-1,4-dihydro-1,4-enthenoanthracene

Abstract
The primary photoproducts of direct and benzophenone sensitized irradiation of the barrelene 1-methoxy-1,4-dihydro-1,4-ethenoanthracene are the semibullvalenes 2- and 5-methoxynaphtho[2,3-c]tricyclo[3.3.0.02,8]-octa-3,6-diene (6 and 7), formed with quantum efficiencies of [Formula: see text] in each case. Whereas 6 is inert to further direct irradiation, 7 photoisomerizes to 6-methoxycycloocta[b]naphthalene (4) (Φ = 0.40); 4 photoisomerizes to 10b-methoxy-2a, 10a-dihydrocyclobut[a]anthracene upon direct (Φ = 0.11) or benzophenone-sensitized irradiation (Φ = 0.05).

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