Flavanoid Expoxides - XIII: Acid and Base Catalysed Reactions of 2'-Tostyloxychalcone epoxides. Mechanism of the Algar-Flynn-Oyamada Reaction

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Title: Flavanoid Expoxides - XIII: Acid and Base Catalysed Reactions of 2'-Tostyloxychalcone epoxides. Mechanism of the Algar-Flynn-Oyamada Reaction
Authors: Gormley, T. R. (Thomas Ronan)
O'Sullivan, W.I.
Permanent link: http://hdl.handle.net/10197/6996
Date: 1973
Online since: 2015-09-09T09:39:48Z
Abstract: 2'-Tosyloxychalcon.e epoxide (6a) on reaction with alkali gave flavonol (4a) while similar treatment of 6'-methoxy-2'-tosyloxychalcone┬Ěepoxide (6b), both at room temperature and. at the boiling point of the reaction medium, afforded 5-methoxyaurone (5b). The latter result indicates that an epoxide is not an intermediate in the production of flavanols from 2'-hydroxy-6'-methoxychalcone epoxides on treatment with alkaline hydrogen peroxide (AFO Reaction) at the higher temperature. Epoxide 6a on treatment with boron trifluoride etherate gave a mixture of flavanonol and flavonol while epoxide 6b gave.formyldesoxybenzoin (9) under similar conditions.
Type of material: Journal Article
Publisher: Elsevier
Journal: Tetrahedron
Volume: 29
Issue: 2
Start page: 369
End page: 373
Keywords: FlavonolFlavanonolOxidation
DOI: 10.1016/S0040-4020(01)93304-6
Language: en
Status of Item: Peer reviewed
Appears in Collections:Agriculture and Food Science Research Collection

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