BASE-CATALYZED ELIMINATION OF PARA-SUBSTITUTED THIOPHENOXIDES FROM 4-(ARYLTHIO)AZETIDIN-2-ONES

被引：8

作者：

GU, HZ ^{[1
]}

FEDOR, LR ^{[1
]}

机构：

[1] SUNY BUFFALO,SCH PHARM,DEPT MED CHEM,BUFFALO,NY 14260

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 21期

关键词：

D O I：

10.1021/jo00308a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previously we postulated the E 1cBRmechanism for reactions of 4-(aryloxy)azetidin-2-ones in aqueous alkali to give para-substituted phenoxide ions and 3-hydroxyacrylamide oxyanion.1 Rate constants for the nucleofugic step can be obtained using this system, and we anticipated that with appropriate 4-substituted azetidin-2-ones we could rank several nucleofuges and possibly obtain a quantitative structure-activity relationship for them.2 Here we report on the E1cBRreactions of 4-(arylthio)azetidin-2-ones 1–6 in aqueous alkali. © 1990, American Chemical Society. All rights reserved.

引用

页码：5655 / 5657

页数：3

共 28 条

[1]

Albert A., 1962, IONIZATION CONSTANTS

[2]

ARNOLDI A, 1990, EUR J MED CHEM, V23, P149

[3] CONVENIENT SYNTHESIS OF ALPHA-(2-OXOAZETIDIN-4-YL) ESTERS AND KETONES AND RELATED SYSTEMS [J].