Fries rearrangement of dibenzofuran-2-yl ethanoate under photochemical and Lewis-acid-catalysed conditions

The Fries rearrangement of dibenzofuran-2-yl ethanoate as a route to o-hydroxyacetyldibenzofurans has been investigated, both under thermal Lewis-acid catalysed and non-catalysed photochemical conditions. The reactions were examined theoretically at semi-empirical (PM3 and ZINDO/S) and density functional theory (DFT) levels. The correct selection of reaction conditions provides viable preparative routes to ortho-acylated hydroxydibenzofurans.