Tetrahedron

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

AMAG Oliveira, AMF Oliveira-Campos, MMM Raposo…

Index: Oliveira, Ana M. A. G.; Oliveira-Campos, Ana M. F.; Raposo, M. Manuela M.; Griffiths, John; Machado, Antonio E. H. Tetrahedron, 2004 , vol. 60, # 29 p. 6145 - 6154

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Citation Number: 9

Abstract

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 ...