25-Alkoxy-26-benzoyloxycalix[4]arenes: the reaction mechanism of benzoyl migration

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• 作者：Lee-Gin Lin^a ; ^{lglin@faculty.pccu.edu.tw} ; Pi-Guey Su^a ; Jun-Ren Huang^a ; Cheng-Han Kuo^a ; Chien-Hung Lin^a ; Chi-Peng Dai^a ; Tahsin J. Chow^b
• 关键词：Calix[4]arene ; Disubstituted calix[4]arenes ; Benzoyl-migration ; Cyclic orthobenzoate-like intermediate
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：4 July, 2012
• 卷：53
• 期：27
• 页码：3510-3513
• 文件大小：266 K

摘要

In the presence of K₂CO₃ as reaction base, the 25-alkoxy-27-benzoyloxy-calix[4]arenes were converted into 25-alkoxy-26-benzoyloxy derivatives by benzoyl-migration. A benzoyl-migrated reaction mechanism with a cyclic orthobenzoate-like intermediate was proposed, and the mechanism was supported by the identical reaction results on the conversion of 25-ethoxy-27-benzoyloxycalix[4]arene to 25-ethoxy-26-benzoyloxycalix[4]arene, and vice versa.