PHOTOCHEMICAL SYNTHESES: 6. THE FORMATION OF HEPTANDIONES FROM ACETYLACETONE AND ALKENES
- 1 February 1963
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 41 (2), 440-449
- https://doi.org/10.1139/v63-061
Abstract
The irradiation of acetylacetone in the presence of oct-1-ene, cyclopentene, cyclohexene, and 1-methylcyclohexene gives substituted heptandiones. These diketones may then be cyclized with acid or base. Irradiation of isopropenyl acetate and acetylacetone gives, after cyclization, m-5-xylenol. The mechanism of the reaction is discussed: it represents the first cycloaddition to an isolated ethylenic linkage.Keywords
This publication has 15 references indexed in Scilit:
- THE PHOTODIMERS OF COUMARIN AND RELATED COMPOUNDSCanadian Journal of Chemistry, 1962
- PHOTOCHEMICAL SYNTHESES: 2. THE IRRADIATION OF ACENAPHTHENE WITH BENZILCanadian Journal of Chemistry, 1962
- PHOTOCHEMICAL SYNTHESES: I. THE REACTION OF ALDEHYDES AND KETONES WITH CYCLOALKENESCanadian Journal of Chemistry, 1961
- Large Tunnelling Corrections in Chemical Reaction Rates.1 IIJournal of the American Chemical Society, 1961
- The Relative Stabilities of cis and trans Isomers. V. The Bicyclo[5.2.0]nonanes. An Extension of the Conformational Rule1,2Journal of the American Chemical Society, 1959
- PHOTOCHEMICAL REACTIONS OF KETONES IN SOLUTIONJournal of the American Chemical Society, 1958
- Photochemical Reactions. VII.1 The Intramolecular Cyclization of Carvone to Carvonecamphor2Journal of the American Chemical Society, 1957
- Light-catalyzed Organic Reactions. I. The Reaction of Carbonyl Compounds with 2-Methyl-2-butene in the Presence of Ultraviolet LightJournal of the American Chemical Society, 1954
- Dimerization Reactions in Sunlight.Chemical Reviews, 1952
- Reactions of Non-enolizable Ketones in Sunlight.Chemical Reviews, 1947