25-Alkoxy-26-benzoyloxycalix[4]arenes: the reaction mechanism of benzoyl migration |
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| Authors: | Lee-Gin Lin Pi-Guey SuJun-Ren Huang Cheng-Han KuoChien-Hung Lin Chi-Peng DaiTahsin J Chow |
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| Institution: | a Institute of Applied Chemistry, Chinese Culture University, Taipei 11114, Taiwan, ROC
b Institute of Chemistry, Academy Sinica, Taipei 11529, Taiwan, ROC |
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| Abstract: | In the presence of K2CO3 as reaction base, the 25-alkoxy-27-benzoyloxy-calix4]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-benzoyloxycalix4]arene to 25-ethoxy-26-benzoyloxycalix4]arene, and vice versa. |
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| Keywords: | Calix[4]arene Disubstituted calix[4]arenes Benzoyl-migration Cyclic orthobenzoate-like intermediate |
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