A novel photochemical structural inversion : the first methoxy–hydroxymethyl isomerization

Abstract

Photolysis of 4-methoxybenzo[b]furan-3(2H)-ones provides the first example of structural inversion of an arylmethoxy-group to the corresponding hydroxymethyl function. Suitable structural parameters permit subsequent rearrangement of the heterocyclic ring to 5-hydroxyisochroman-4-ones. By contrast photolysis of the isomeric 4-methoxybenzo[b]furan-2(3H)-one leads directly to the deoxybenzoin analogue.