Reactions of ß-ARYL Lignin Model Quinone Methides with Anthrahydroquinone and Anthranol

Quinone methides prepared in situ from phenylcoumaran and ß-C-l lignin models which did not contain a ß-hydroxymethyl group, readily formed addition products with anthranol but not with anthrahydroquinone. For ß-aryl lignin models containing the hydroxymethyl group, the retro-aldol reaction (liberating formaldehyde) was so facile under the conditions used that stilbene formation from the quinone methide took precedence over adduct formation.