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Wagner-Jauregg reaction



The Wagner-Jauregg reaction is a classic organic reaction in organic chemistry (named after its inventors) 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.[1]

Additional recommended knowledge

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:[2]


References

  1. ^ Wagner-Jauregg, Ber., 68, 3218 (1930); Ann., 401, 1 (1931)
  2. ^ 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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Wagner-Jauregg_reaction". A list of authors is available in Wikipedia.
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