Kinetics and mechanism of the cyclisation of some 2′-hydroxy-chalcone epoxides and subsequent elimination reactions of aurone hydrates

CJ Adams, L Main

Index: Adams, Christopher J.; Main, Lyndsay Tetrahedron, 1992 , vol. 48, # 45 p. 9929 - 9938

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Citation Number: 10

Abstract

Analysis of the pH-rate profile for the cyclisation of the monoanion of 2′-hydroxychalcone epoxide which gives 3-hydroxyflavanone and of some 6′-alkoxy-substituted analogues which give mostly hydrate, gives rate coefficients which quantify the preference for α over β cyclisation when 6′-substituents are present. These are considered in terms of stereoelectronic factors which may be responsible for the preference. Also reported are ...