2014年
Studies on the stereochemical assignment of 3-acylidene 2-oxindoles
ORGANIC & BIOMOLECULAR CHEMISTRY
- ,
- ,
- ,
- ,
- ,
- ,
- 巻
- 12
- 号
- 20
- 開始ページ
- 3201
- 終了ページ
- 3210
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1039/c4ob00496e
- 出版者・発行元
- ROYAL SOC CHEMISTRY
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.
- リンク情報
- ID情報
-
- DOI : 10.1039/c4ob00496e
- ISSN : 1477-0520
- eISSN : 1477-0539
- Web of Science ID : WOS:000335336800008