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Allan–Robinson reaction

Chemical reaction

Chemical reaction

The Allan–Robinson reaction is the chemical reaction of o-hydroxyaryl ketones with aromatic anhydrides to form flavones (or isoflavones).{{cite book | author =Jie Jack Li | title =Name Reactions. A Collection of Detailed Reaction Mechanisms 4th Edition | publisher =Springer | location =Berlin, De | year =2009

If aliphatic anhydrides are used, coumarins can also be formed. (See Kostanecki acylation.) :[[File:Allan Robinson Reaction Overview.tif|none|thumb|489x489px|Reaction overview]]

Mechanism

:[[File:Allan-Robinson reaction mechanism.png]]

The o-hydroxyaryl ketone first undergoes tautomerization to form the respective enol. The pi electrons of the double bond then attack the electrophilic carbon of the anhydride; a carboxylate anion is subsequently lost as a leaving group. The carboxylate anion then attacks an alpha hydrogen to form an enol. The nucleophilic hydroxyl group then attacks the carbonyl carbon to form a six-membered heterocyclic ring. A proton is abstracted from the hydroxyl group of the enol to form a ketone, and the remaining hydroxyl group is lost as a leaving group in a concerted step to afford the final product.

References

References

  1. Allan, J.; Robinson, R. ''[[J. Chem. Soc.]]'' '''1924''', ''125'', 2192.
  2. Dyke, S. F.; Ollis, W. D.; Sainsbury, M. ''[[J. Org. Chem.]]'' '''1961''', ''26'', 2453. ({{doi. 10.1021/jo01351a072)
  3. Wheller, T. S.. (1952). "Flavone". [[Organic Syntheses]].
  4. Graham, Solomons, T. W.. (17 January 2013). "Organic chemistry".
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