Journal of the American Chemical Society p. 998 - 1007 (1982)
Update date:2022-08-02
Topics:
Salomon
Coughlin
Ghosh
Zagorski
Cyclobutylcarbinyl alcohols of the bicyclo left bracket 3. 2. 0 right bracket heptane ring system are produced by UV irradiation of alpha -, beta -, and gamma -alkenylallyl alcohols in the presence of copper (I) trifluoromethanesulfonate (CuOTf). endo-2-Hydroxy epimers of bicyclo left bracket 3. 2. 0 right bracket heptan-2-ols are generated stereoselectively. This result as well as the effect of CuOTf on the **1H NMR spectrum of 4,4-dimethyl-1,6-heptadien-3-ol suggests that coordination of two C equals C bonds and the hydroxyl group with a single copper (I) is important. The derived bicyclo left bracket 3. 2. 0 right bracket heptan 2-ones fragment cleanly at 580 degree C to afford cyclopent-2-en-1-ones. Geometric isomerization competes with photobicyclization of (E)- and (Z)-octa-2,7-dien-1-ols.
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