Wolff rearrangement

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The Wolff rearrangement is a chemical reaction in which ketenes are obtained from diazo compounds with a carbonyl group adjacent to the diazo group :

The Wolff rearrangement

The reaction can take place photochemically under the influence of UV radiation , thermally under the influence of heat or under catalysis by heavy metals ( Ag 2 O ). Depending on the reaction conditions, the ketenes can be reacted further directly or isolated in bulk.

The rearrangement of the α-diazoketones was named after its discoverer, the German chemist Ludwig Wolff (1857-1919).

Individual evidence

  1. H. Meier, K.-P. Zeller: The Wolff Rearrangement of α-Diazo Carbonyl Compounds , Angew. Chem. Int. Ed. Engl. 14 ( 1975 ) 32-43.
  2. W. Kirmse: 100 Years of the Wolff Rearrangement , Eur. J. Org. Chem. 2002 , 2193-2256.