Oxidation of ethyl trans- and cis-3-bromo-1-methyl-2-oxocyclohexanecarboxylates by dimethyl sulphoxide
Abstract
Ethyl c-3-bromo-1-methyl-2-oxocyclohexane-r-1-carboxylate (1a) is oxidized by dimethyl sulphoxide to the 2,3-dione derivative (3), whereas the t-3-bromo-isomer (1b) is apparently dehydrogenated to give the bromocyclohexenone (4). The mechanism for the formation of the product (4) is discussed. Allied reactions are described.