- Wagner-Jauregg reaction
The Wagner-Jauregg reaction is a classic
organic reaction inorganic chemistry , named afterTheodor Wagner-Jauregg , describing theDiels-Alder reaction of 2 equivalents ofmaleic anhydride with a 1,1-diarylethylene. Afteraromatization of the bis-adduct the ultimate reaction product is anaphthalene compound with onephenyl 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 acopolymer . 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 anddecarboxylation withbarium hydroxide andcopper : ["The Condensation of 1,1-Diarylethylenes with Maleic Anhydride" Felix Bergmann, Jacob Szmuszkowicz, and George FawazJ. Am. Chem. Soc. ; 1947; 69(7) pp 1773 - 1777; DOI|10.1021/ja01199a055]References
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