The Stereochemistry of Adduct Formation between a Lignin Model Quinone Methide and Anthrone, 10-Methylanthrone and 10-Phenylanthrone.

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Abstract
Anthrone, 10-methylanthrone and 10-phenylanthrone reacted with the quinone methide derived from a phenolic lignin model compound, [1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1-propanol], forming adducts similar to those believed to be intermediates in anthraquinone accelerated delignification reactions. Both threo and erythro isomers were obtained for the anthrone and 10-methylanthrone adducts. The reactions are assumed to be thermodynamically controlled; the threo isomer is formed faster. The stereochemistry of the 10-phenylanthrone adduct could not be resolved on the basis of the NMR spectra recorded.

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