Wagner-Jauregg reaction

The Wagner-Jauregg reaction is a classic organic reaction in organic chemistry, named after Theodor Wagner-Jauregg, describing the Diels-Alder reaction of 2 equivalents of maleic anhydride with a 1,1-diarylethylene. After aromatization of the bis-adduct the ultimate reaction product is a naphthalene compound with one phenyl substituent. [Theodor Wagner-Jauregg, Ber., 68, 3218 (1930) DOI|10.1002/cber.19300631140] [Theodor Wagner-Jauregg, Ann., 491, 1 (1931)DOI|10.1002/jlac.19314910102]

The reaction is unusual in that the anhydride reacts with the related styrene to form a copolymer. The presence of the alpha-phenyl group activates the styryl group for a Diels–Alder reaction even at the expense of its aromaticity.

In one adaptation rearomatization is accomplished with elemental sulfur and decarboxylation with barium hydroxide and copper: ["The Condensation of 1,1-Diarylethylenes with Maleic Anhydride" Felix Bergmann, Jacob Szmuszkowicz, and George Fawaz J. Am. Chem. Soc.; 1947; 69(7) pp 1773 - 1777; DOI|10.1021/ja01199a055]

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