Algar–Flynn–Oyamada reaction
Source: Wikipedia, the free encyclopedia.
The Algar–Flynn–Oyamada reaction is a
Reaction mechanism
There are several possible mechanisms to explain this reaction; however, these reaction mechanisms have not been elucidated. What is known is that a two-stage mechanism exists. First, dihydroflavonol is formed, which then subsequently oxidizes to form a flavonol.
Proposed mechanisms involving
epoxidation of the alkene have been disproven.[3]
The probable mechanisms are thus two possibilities:
- The phenoxide attacks the enone at the beta position, and the alkene directly attacks hydrogen peroxide from the alpha position, forming the dihydroflavonol.
- The phenoxide attacks the enone at the beta position, closing the six-membered ring and forming an enolate intermediate. The enolate then attacks hydrogen peroxide, forming the dihydroflavonol.
See also
References
- ^ Algar, J.; Flynn, J. P. (1934). Proceedings of the Royal Irish Academy. 42B: 1.
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- ISSN 0040-4020.