A study on the activation of carboxylic acids by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 2-chloro-4,6-diphenoxy-1,3,5-triazine

被引：134

作者：

Kaminski, ZJ ^{[1
]}

Paneth, P ^{[1
]}

Rudzinski, J ^{[1
]}

机构：

[1] Lodz Tech Univ, Fac Chem, PL-90924 Lodz, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 13期

关键词：

D O I：

10.1021/jo972020y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Activation of carboxylic function by means of 2-chloro-4,6-disubstituted-1,3,5-triazines 1 and 2 leading to triazine esters was found to be a multistep process with participation of quarternary triazinylammonium salts 3-6 as the intermediates, with the rate of reaction strongly dependent on the structure of the tertiary amine. The studies on alkylation of tertiary amines with CDMT revealed the two-step process A(N) + D-N, and zwitterionic addition product 9 was identified by H-1 NMR spectroscopy. Semiempirical modeling of the reaction as well as measured nitrogen and chlorine isotope effects also support this mechanism.

引用

页码：4248 / 4255

页数：8

共 42 条

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[13] STRUCTURES OF AROMATIC ESTERS OF 2,2-DIMETHYLPROPANOIC ACID - 4,6-DIMETHOXY-1,3,5-TRIAZIN-2-YL 2,2-DIMETHYLPROPANOATE (1) AND 4-NITROPHENYL 2,2-DIMETHYLPROPANOATE (2) [J].