Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

被引：26

作者：

Edeson, Steven J. ^{[1
]}

Jiang, Julong ^{[1
]}

Swanson, Stephen ^{[2
]}

Procopiou, Panayiotis A. ^{[2
]}

Adams, Harry ^{[1
]}

Meijer, Anthony J. H. M. ^{[1
]}

Harrity, Joseph P. A. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 20期

基金：

英国工程与自然科学研究理事会;

关键词：

ELUCIDATION; COMPLEXES; ACID; DFT;

D O I：

10.1039/c4ob00496e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.

引用

页码：3201 / 3210

页数：10

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