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A study of the reactions of flavanoids with nucleophiles

Abstract:

The reactions with nucleophiles of 4-substituted flavans variously methoxylated are studied. The partial epimerisation of 4β-acetoxyflavans in acetic acid/acetic anhydride mixtures and of flavan-4β-ols in aqueous acid, providing preparatively useful routes to 4α-acetoxyflavans and flavan-4α-ols, occur by an SN1 mechanism. Reaction is greatly facilitated by methoxyl groups at the 5- and, especially, the 7-position. No effect of B-ring substitution on reaction rates was detected. ...

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Peer review status:
Peer reviewed

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Department:
University of Oxford
Role:
Author
Type of award:
DPhil
Level of award:
Doctoral
Awarding institution:
University of Oxford
UUID:
uuid:039d7203-b2bb-4d37-9986-a738fb1857fe
Local pid:
polonsky:12:4
Source identifiers:
601870725
Deposit date:
2017-10-05

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