The occurrence of an hydride shift in the aromatisation of 1,4-epoxy-1,4-dihydronaphthalenes

Abstract

The acid-catalysed aromatisation of [1,4-2H2]- 1,4-epoxy-1,4-dihydronaphthalene and [4-2H]-1,4-epoxy-1-methyl-1,4-dihydronaphthalene is shown to result in partial retention of deuterium at the 2-position of 1-naphthol and 4-methyl-1-naphthol, respectively.