Diels-Alder Reactions of Lignin-Derived Quinones
- 1 December 1989
- journal article
- research article
- Published by Taylor & Francis in Journal of Wood Chemistry and Technology
- Vol. 9 (4) , 513-534
- https://doi.org/10.1080/02773818908050313
Abstract
The Diels-Alder reactions of methoxy-p-benzoquinone and 2,6-dimethoxy-p-benzoquinone, which may be obtained from lignin and lignin model compounds, and of o-quinones (4-methyl, 4-acetyl, and 4-(l-hydroxyethyl)-o-benzoquinone) were investigated using 2,3-dimethylbutadiene, isoprene and styrene as dienes. Dimethylbutadiene and isoprene were found to be effective reactants, resulting in the generation of several Diels-Alder addition products. Loss of the methoxyl group and the side chain were observed under certain conditions. Reactions of the p-benzoquinones went more smoothly than the reactions of the o-quinones, and product yields were generally higher. Higher yields of anthraquinone products were obtained from 2,6-dimethoxy-p-benzoquinone than from methoxy-p-benzoquinone.This publication has 11 references indexed in Scilit:
- Lignin-Derived Quinones as Pulping AdditivesJournal of Wood Chemistry and Technology, 1989
- The Generation of Quinones from Lignin and Lignin-Related CompoundsJournal of Wood Chemistry and Technology, 1989
- Hexacyanoferrate-catalyzed oxidation of trimethoxybenzenes to dimethoxy-p-benzoquinones with hydrogen peroxideThe Journal of Organic Chemistry, 1985
- Some Derivatives of 1-Benzazepine. Part IICanadian Journal of Chemistry, 1974
- Diels-Alder Reactions of Benzoquinone. I. Reactions of Methoxybenzoquinone with Styrene and o-MethylstyreneBulletin of the Chemical Society of Japan, 1971
- 556. The Diels–Alder reaction of p-benzoquinonesJournal of the Chemical Society, 1963
- Estimation of Phenolic Hydroxyl Groups in Lignin. I. Periodate Oxidation of Guaiacol Compounds.Acta Chemica Scandinavica, 1955
- STUDIES IN THE POLYOXYPHENOL SERIES: VIII. THE OXIDATION OF SUBSTANCES RELATED TO VANILLIN WITH SODIUM CHLORITE AND CHLORINE DIOXIDECanadian Journal of Chemistry, 1955
- Naphthoquinone Antimalarials. III. Diene Synthesis of 1,4-Naphthoquinones1Journal of the American Chemical Society, 1948
- Studies on the formation of complex oxidation and condensation products of phenols. A contribution to the investigation of the origin and nature of humic acid. Part I. ─Studies of the reactivity of simple monocyclic quinonesProceedings of the Royal Society of London. Series A, Containing Papers of a Mathematical and Physical Character, 1933