Exploring sources of catalysis in the basic elimination of 5-nitrobenzisoxazole

被引：3

作者：

Hannak, RB

Rojas, CM

机构：

[1] Scripps Res Inst, Dept Chem & Mol Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期

基金：

美国国家科学基金会; 美国国家卫生研究院; 奥地利科学基金会;

关键词：

benzimidazoles; elimination reaction; host compounds; catalysis;

D O I：

10.1016/S0040-4039(98)00596-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A C-shaped, bifunctional host with a highly preorganized cleft was used as a host system to investigate the sources of catalysis in the base-promoted conversion of 5-nitrobenzisoxazole to 2-cyano-5-nitrophenolate. Kinetic studies with compounds that partly conserve structural elements of the host suggest that pi-stacking interactions and solvation effects mainly contribute to the observed rate acceleration of the host compared to the acetate promoted reaction. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：3465 / 3468

页数：4

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