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Polar Substituents in Benzobarrelene Photochemistry; The Photoreactivities of Dimethyl 10-methoxy- and Dimethyl 10,11-dimethoxy-2,3-benzobicyclo[2.2.2]octateraene-5,6-dicarboxylate

✍ Scribed by Christopher Owen Bender; John Wilson

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
651 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The direct irradiation of the monomethoxybarrelene 8 gives cyclooctatetraene product 18 (Φ = 0.075) via the anti‐Epiotis aromatic‐vinyldiester [2π+2π] bridging route, and two semibullvalenes 16 (Φ = 0.075) and 17 (Φ = 0.075) from di‐π‐methane rearrangements initiating from vinyl‐vinyldiester bridging. Benzophenone sensitization yields 16 (Φ =0.11) and 17 (Φ = 0.11). The dimethoxybarrelene 9 gives only semibullvalene 10, this resulting from di‐π‐methane rearrangement involving the vinyl and vinyldiester bridges, upon direct (Φ = 0.009) or benzophenone sensitized irradiations (Φ = 0.38). 10 undergoes a vinylcyclopropane rearrangement to give semibullvalene 11 upon direct or acetone sensitized irradiations (Φ = 0.008).

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