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
This publication has 13 references indexed in Scilit:
- Organic photochemistry. XXXVIII. Photochemistry without light and the stereochemistry of the type A dienone rearrangementJournal of the American Chemical Society, 1969
- Organic photochemistry. XXXVI. Photochemistry without light and the stereochemistry of the type A dienone rearrangementJournal of the American Chemical Society, 1968
- Photochemistry of 4-methyl-4-trichloromethyl-2,5-cyclohexadienone. II. Mechanistic studies and characterization of the excited stateJournal of the American Chemical Society, 1968
- A criterion for zwitterionic intermediates in the photochemistry of 2,5-cyclohexadienonesJournal of the American Chemical Society, 1968
- Photo-induced reactions. VI. The photochemical formation of the ketone tautomer of a phenol from 2,4,6-tri-tert-butyl-4-methoxy-2,5-cyclohexadienoneJournal of the American Chemical Society, 1967
- Photochemical Rearrangements of Conjugated Cyclic Ketones: The Present State of InvestigationsPublished by Wiley ,1966
- Selection Rules for Sigmatropic ReactionsJournal of the American Chemical Society, 1965
- A New Approach to Mechanistic Organic PhotochemistryPublished by Wiley ,1963
- Photochemical Rearrangements of Organic MoleculesPublished by Wiley ,1963
- A New Approach to Mechanistic Organic Photochemistry. IV. Photochemical Rearrangements of 4,4-DiphenylcyclohexadienoneJournal of the American Chemical Society, 1962