The Photochemical Reaction of α-Diketones
- 1 March 1972
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 45 (3) , 847-851
- https://doi.org/10.1246/bcsj.45.847
Abstract
The relative photochemical reactivity of α-diketones, in particular, 9,10-phenanthraquinone, 1,2-naphthoquinone, acenaphthoquinone, benzil, 4,4′-dimethylbenzil, 2,4,6-trimethylbenzil, 2,5,2′,5′-tetramethylbenzil, 2,3,5,6-tetramethylbenzil, 2,4,6,2′,4′,6′-hexamethylbenzil, phenylglyoxal, 2,5-dimethylphenylglyoxal, and 2,4,6-trimethylphenylglyoxal was investigated in hydrogen donating solvents. Type of the product and relative reactivity differ widely according to the structure of α-dike tones. Whereas 9,10-phenanthraquinone gives 1,4-adduct (V) in a hydrogen donating solvent (THF), 2,5,2′,5′-tetramethylbenzil gives 2-hydroxy-2-(2′,5′-dimethylphenyl)indanone (VII) via intramolecular hydrogen abstraction in nearly quantitative yield. No photochemical reaction of 2,4,6-trimethylbenzil or 2,3,5,6-tetramethylbenzil could be observed in the same solvent even under a long irradiation.This publication has 11 references indexed in Scilit:
- Chemically Induced Dynamic Nuclear Polarization in the Photochemical Reaction of Phenanthraquinone with Hydrogen Donors. II. A Consideration of Unusual Nuclear Spin PolarizationBulletin of the Chemical Society of Japan, 1971
- Chemically Induced Dynamic Nuclear Polarization in the Photochemical Reaction of Phenanthraquinone with Hydrogen Donors. I. Kinetics of Nuclear Spin PolarizationBulletin of the Chemical Society of Japan, 1971
- The Reaction of Photo-excited Phenanthraquinone with Hydrogen Donors. The Behaviors of the Resulting 1,2-Photoadducts Studied by the CIDNP TechniqueBulletin of the Chemical Society of Japan, 1971
- Photochemical Reactions of Phenanthraquinone with Hydrogen Donors. An Investigation of the Reaction by CIDNP MethodBulletin of the Chemical Society of Japan, 1971
- Relative Rate of Hydrogen Abstraction by the Triplet State of PhenanthraquinoneBulletin of the Chemical Society of Japan, 1969
- Mechanisms of photochemical reactions in solution. LVIII. Photoreduction of camphorquinoneJournal of the American Chemical Society, 1969
- The photolysis of benzil in cyclohexane solutionCanadian Journal of Chemistry, 1968
- Photochemical Reactions of Diketones. II.1a,b The 1,2-Addition of Substituted Toluenes to 9,10-PhenanthrenequinoneThe Journal of Organic Chemistry, 1964
- Photochemical Reactions of Diketones. The 1,4-Addition of Ethers to 9,10-PhenanthrenequinoneThe Journal of Organic Chemistry, 1963
- Ueber das Isobenzil und die Einwirkung des Sonnenlichts auf einige organische SubstanzenEuropean Journal of Inorganic Chemistry, 1886