Synthesis and Dynamic NMR Study of Atropisomerism in Stable 1,4-Diionic Phosphorus Compounds
- 1 January 2002
- journal article
- research article
- Published by Taylor & Francis Ltd in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 177 (1), 93-103
- https://doi.org/10.1080/10426500210216
Abstract
The addition of triphenylphosphine to acetylenic ketones in the presence of strong CH-acids, such as Meldrom's acid, N , N '-dimethylbarbituric acid, dimedone, or indane-1,3-dione leads to 1,4-diionic organophosphorus compounds. Dynamic NMR study of these stable betaines show an unusually high sixfold energy barrier for rotation around the sp 2 -sp 3 carbon-carbon single bond, which leads to an observable atropisomerism.Keywords
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