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Baker-Venkataraman rearrangement



The Baker-Venkataraman rearrangement is the chemical reaction of 2-acetoxyacetophenones with base to form 1,3-diketones.[1][2]

This rearrangement reaction proceeds via enolate formation followed by acyl transfer.

The Baker-Venkataraman rearrangement is often used to synthesize chromones and flavones.[3][4][5]


References

  1. ^ Baker, W. (1933). "Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones". J. Chem. Soc.: 1381–1389. doi:10.1039/JR9330001381.
  2. ^ Mahal, H. S.; Venkataraman, K. (1934). "Synthetical experiments in the chromone. group. XIV. Action of sodamide on 1-acyloxy-2-acetonaphthones". J. Chem. Soc.: 1767–1769. doi:10.1039/JR9340001767.
  3. ^ T. S. Wheeler (1952). "Flavone". Organic Syntheses 32: 72. (also in the Collective Volume (1963) 4:478 (PDF)).
  4. ^ Jain, P. K.; et al. (1982). "A Facile Baker-Venkataraman Synthesis of Flavones using Phase Transfer Catalysis". Synthesis: 221–222. doi:10.1055/s-1982-29755.
  5. ^ Kalinin, A. V.;Da Silva, A. J. M.;Lopes, C. C.;Lopes, R. S. C.;Snieckus, V. (9 July 1998). "Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins". Tetrahedron Lett. 39 (28): 4995–4998. doi:10.1016/S0040-4039(98)00977-0.

See also

  • Allan-Robinson reaction
  • Kostanecki acylation
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Baker-Venkataraman_rearrangement". A list of authors is available in Wikipedia.
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