The Journal of organic chemistry

Mechanistic studies of the biomimetic epoxy ester-orthoester and orthoester-cyclic ether rearrangements

JL Giner, X Li, JJ Mullins

Index: Giner, Jose-Luis; Li, Xiaoyong; Mullins, Joseph J. Journal of Organic Chemistry, 2003 , vol. 68, # 26 p. 10079 - 10086

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Citation Number: 22

Abstract

The relative rates of acid-catalyzed rearrangements of epoxy esters to [3.2. 1] bicyclic orthoesters, the subsequent rearrangements of these ortho esters to substituted tetrahydrofurans, and the rates of orthoester hydrolysis at pH 4.75 were measured in NMR kinetics experiments. The ease of formation and stabilities of these orthoesters compared favorably with the OBO-type [2.2. 2] bicyclic orthoesters typically used as protecting groups ...