The Thiele-Winter Acetoxylation of Quinones

McOmie, J. F. W.; Blatchly, J. M.


In 1898, Johannes Thiele described the reaction of p-benzoquinone with acetic acid in the presence of a small quantity of sulfuric acid to give 1,2,4-triacetoxybenzene in 80% yield. Later Thiele and Winter described further experiments that showed both 1,2- and 1,4-naphthoquinone gave 1,2,4-triacetoxynaphthalene and that the same product was obtained when sulfuric acid was replaced by zinc chloride. Thiele-Winter acetoxylation can be defined as the acid-catalyzed reactions of quinones with acetic acid to give triacetoxy aromatic compounds. This reaction has been carried out on a large number of quinones and to this point there has been no review. Very little work has been done on the reaction of quinones with anhydrides other than acetic anhydride. Results of these studies are summarized. Reactions with other anhydrides are discussed.