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   ARNDT-EISTERT homologation



 
 
mechanism:


 

remarks:

  • Goes through a a-keto-carbene.
  • The key step is the Wolff rearrangement of the diazoketone to ketene.

 references:

Tetrahedron: Asymmetry 2005, 16, 857.
Eur. J. Org. Chem. 2002, 2193. (review)
Angew. Chem. Int. Ed. 1995, 34, 471.
Tet. Lett. 1979, 29, 2667-2670.
Organic Reactions 1942, 1, 38.