SUBSTRATE ACIDITIES AND CONVERSION TIMES FOR REACTIONS OF AMIDES WITH DI-TERT-BUTYL DICARBONATE

被引：24

作者：

HANSEN, MM

HARKNESS, AR

COFFEY, DS

BORDWELL, FG

ZHAO, YY

机构：

[1] Chemical Process Research and Development Division, Lilly Research Laboratories, A Division of Eli Lilly and Company, Indianapolis

[2] Department of Chemistry. Northwestern University., Evanston, IL 60208-3113

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 49期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(95)01931-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conversion time for 4-dimethylaminopyridine catalyzed reaction of amides with di-tert-butyl dicarbonate varies dramatically with substrate acidity. The pK(a)'s in DMSO of some amides are determined to support correlation of reactivity with substrate acidity. Particularly acidic substrates, such as 4-thiazolidinone, readily react with a variety of dialkyl dicarbonates. Less acidic substrates react with Boc(2)O but other dialkyl dicarbonates decompose preferentially.

引用

页码：8949 / 8952

页数：4

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