Photoinduced Reactions. XLI. Stereochemical Course in the Photochemistry of a 2,5-Cyclohexadienone
- 1 September 1970
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 43 (9) , 2891-2893
- https://doi.org/10.1246/bcsj.43.2891
Abstract
Mechanism for the photochemical transformation of a 2,5-cyclohexadienone into a bicyclo[3.1.0]hex-3-en-2-one (so-called lumiketone) was discussed. Photolysis of 2,4,6-tri-t-butyl-4-methoxy-2,5-cyclohexadienone (VII) gave only one stereoisomer (VIIIa) of the corresponding lumiketones. This fact and the prediction by the Woodward-Hoffmann rule indicate that a biradical-like excited state XI with 3,5-bonding gives rise to a direct rearrangement to lumiketone Villa as shown in Path B (Scheme II).Keywords
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