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异腈与羧酸在穴状配体中的反应:对难以捉摸的异酰亚胺中间体的观察

Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

作者信息

Restorp Per, Rebek Julius

机构信息

The Skaggs Institute for Chemical Biology, 10550 North Torrey Pines Road, La Jolla, California, 92037, USA.

出版信息

J Am Chem Soc. 2008 Sep 10;130(36):11850-1. doi: 10.1021/ja803854r. Epub 2008 Aug 13.

Abstract

A deep cavitand with an inwardly directed carboxylic acid function reacts with small aliphatic isonitriles to form N-acyl formamides inside the cavity. The unique isolation and stabilization of covalently bound guests within the structured environment of the cavitand allows for observation of the labile O-acyl isoimide intermediate using conventional spectroscopic methods.

摘要

一种带有向内羧酸官能团的深穴体与小脂肪族异腈反应,在穴腔内形成N-酰基甲酰胺。穴体结构环境内共价结合客体的独特隔离和稳定作用,使得可以使用传统光谱方法观察不稳定的O-酰基异亚胺中间体。

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本文引用的文献

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Reaction of an Introverted Carboxylic Acid with Carbodiimide.内向型羧酸与碳二亚胺的反应。
Tetrahedron. 2007 Jul 9;63(28):6506-6511. doi: 10.1016/j.tet.2007.03.075.
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Cavitands: organic hosts with enforced cavities.穴合剂:具有强制空腔的有机主体。
Science. 1983 Mar 11;219(4589):1177-83. doi: 10.1126/science.219.4589.1177.

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