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On the photoisomerization of bicyclo[3.2.1]octadienones

✍ Scribed by Harold Hart; George M. Love

Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
156 KB
Volume
12
Category
Article
ISSN
0040-4039

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✦ Synopsis

Bicyclo[3.2.l]octadienones with the general structure & photoisomerize to ketenes 4 and give products derived therefrom.ls3 The corresponding 3,4-benzo&tadienones 2 undergo reversible 1,3-acyl shifts ($ti,$).4 We now wish to report that the other possible (i.e., 6,7-) benzo derivatives of &, undergo a facile photoisomerization which is both synthetically useful and mechanistically interesting. Acid-catalyzed rearrangement of the hexamethyl12.2.2ldienone 2' gives a mixture of ketones 2 -g.4*6 A degassed solution of Q (200 mg) in 5 ml of spectroscopic grade acetone, when irradiated (Pyrex, 450 watt Banovia lamp, 50 min) gave a 100% yield of o.7 Similar 3563

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Wavelength dependent photoisomerization
Wavelength dependent photoisomerization of bicyclo[3.1.0]hexenones
✍ William G. Dauben; Jeffrey M. Cogen; Victor Behar; Arthur G. Schultz; William Ge πŸ“‚ Article πŸ“… 1992 πŸ› Elsevier Science 🌐 French βš– 236 KB

The unusual wavelength dependent product selectivity observed upon irradiation of a substituted 2,5-cyclohexadien-l-one is shown to result from wavelength dependent quantum yields for rearrangement of the primary photoproduct bicyclo[3.l.O]hexenones. Reaction selectivity can be optimized by careful