“Phosphylated” covers phosphorylated, phosphonylated and phosphinylated.
Article first published online: 2 SEP 2010
Copyright © 1968 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Recueil des Travaux Chimiques des Pays-Bas
Volume 87, Issue 6, pages 673–686, 1968
How to Cite
van Hooidonk, C., Kraaij, G. W. and Ginjaar, L. (1968), On the reactivity of organophosphorus compounds: Part IV. The alkaline hydrolysis of some O-phosphylated 2-pyridine oximes. Recl. Trav. Chim. Pays-Bas, 87: 673–686. doi: 10.1002/recl.19680870607
Part III: C. van Hooidonk and L. Ginjaar, Rec. Trav. Chim. 86, 449 (1967).
A preliminary communication of this work appeared in Chem. Ind. London 1966, 702.
- Issue published online: 2 SEP 2010
- Article first published online: 2 SEP 2010
- Manuscript Received: 23 JAN 1968
The rates of alkaline hydrolysis of a number of O-phosphylated 2-pyridine oximes, C5H4NC(R1)NOP(O)R2R3, at different temperatures have been determined. The second-order rate constants and the values of ΔH* and ΔS* are reported. Two parallel pathways of hydrolysis are observed: a nucleophilic substitution reaction on phosphorus (SN2P) generating the oxime and the parent acid and an elimination reaction of the Beckmann type (E2 or ElcB) producing the nitrile and the parent acid. The effects of the groups R1, R2 and R3 on the rates of substitution and elimination are discussed.