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Wessely-Moser Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr665

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Wessely-Moser Rearrangement. Comprehensive Organic Name Reactions and Reagents. 665:2983–2987.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Wessely–Moser rearrangement is an acid- or a base-promoted isomerization of flavones or flavonoids having an unprotected hydroxy group at position 5, involving an opening of the flavone heterocycle and ring closure of the β-diketone intermediate. It has been reported that the Wessely–Moser rearrangement also occurs for natural products containing a flavone component. In addition, the Wessely–Moser rearrangement has also been observed during the acidic hydrolysis of glycosides with flavone as an aglycone and the acidic demethylation of flavones and xanthones. It has also been observed that the 5-hydroxy group is necessary for the occurrence of Wessely–Moser rearrangement. This rearrangement has certain applications in organic synthesis and is useful for the structural rationalization of the natural products.

Keywords:

  • flavones;
  • xanthones;
  • orientin;
  • Gibbs test