Author:
Garrigues B.,Boyer D.,Munoz A.
Abstract
The P—H proton of phosphoranes containing an α-hydroxy acid or iminodiacetic acid ligand is sufficiently mobile to be removed at room temperature by medium strength bases such as triethylamine. The deprotonation products identified by 31P nmr are (a) the phosphoranide for the bicyclic compound prepared from iminodiacetic acid, (b) the anionic phosphite isomeric to the above, for phosphoranes containing the α-hydroxy acid ligand, (c) the phosphite and the phosphoramide in equilibrium, for phosphoranes containing two α-hydroxy ligands. The pKa values potentiometrically determined in DMF solution by titration of the phosphoranes with triethylamine correspond to weak or mild acids. However, the phosphoranes studied are more acid in DMF than other known compounds containing the P—H bond. They are also more dissociated in this solvent than carboxylic acids. [Journal translation]
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
16 articles.
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