CATALYTIC INTRAMOLECULAR PARTICIPATION OF AMIDE GROUP IN THE ACID-HYDROLYSIS OF METHYL-ETHER LINKAGE

被引：11

作者：

ARCELLI, A

PORZI, G

SANDRI, S

机构：

[1] Dipartimento di Chimica G. Cramician, 40126 Bologna

来源：

TETRAHEDRON | 1995年 / 51卷 / 35期

关键词：

D O I：

10.1016/0040-4020(95)00556-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Evidence for the acid catalyzed hydrolysis of methyl ether linkage assisted by the neighboring amide function was obtained. The hydrolysis rate of 1 to 3 was measured at least 1.7x10(3) fold higher than that of the reference compound 5. The values of thermodynamic parameters suggest that the participation of neighboring amide group in 1 is accompanied by a lower activation enthalpy with respect to the unassisted reaction in 5. Experimental evidence. such as the kinetic isotope ratio. the positive phi value of Bunnett-Olsen equation and Delta S-double dagger value suggests an A(2) mechanism.

引用

页码：9729 / 9736

页数：8

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