Quinones and quinone methides. VI. Reactions of 2-Arylmethyl- and 2-(1-Arylethyl)- 1,4-benzoquinones with 4-hydroxy-2H-1-benzopyran-2-one

Abstract

In alcoholic potassium hydroxide 2-methoxy-5-(4-methoxyphenylmethyl)- 1,4-benzoquinone (I) reacts with 4-hydroxy-2H-1-benzopyran-2-one (7) to yield the quinol (8a). In pyridine, however,(1) tautomerizes to the ortho-quinone methide which combines with (7) to yield (17a). 2-(1- Arylethyl-1,4-benzoquinones yield quinols related to (8a) in both alcoholic potassium hydroxide and pyridine solutions; this indicates that quinones methides which might be formed from these quinones are relatively unreactive to nucleophiles.