Acid-catalysed rearrangements in the furan series. II. The solvolysis of 2-acetylfuran oxime toluene-p-sulphonate in methanol

Abstract

The product formed when 2-acetylfuran oxime toluene-p-sulphonate is solvolysed in methanol has been shown to possess the structure 2-acetyl-2,5-dimethoxy-2,5-dihydrofuran. Acid-catalysed rearrangement of the product in methanol occurs readily with the formation of methyl 4,5-dioxohexanoate. The structure of the rearrangement product has been confirmed by synthesis.