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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.12
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:3
References
- ^ Theodor Wagner-Jauregg (1930). "Über addierende Hetero-polymerisation". Ber. 68: 3218. doi:.
- ^ Theodor Wagner-Jauregg (1931). "Die Addition von Maleinsäureanhydrid an asymm. Diphenyl-äthylen". Ann. 491: 1. doi:.
- ^ Felix Bergmann, Jacob Szmuszkowicz, and George Fawaz (1947). "The Condensation of 1,1-Diarylethylenes with Maleic Anhydride". J. Am. Chem. Soc. 69 (7): 1773–1777. doi:.
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