Tetrahedron

Contribution of ring strain and the stereoelectronic effect to the hydrolysis of cyclic five-membered ring phosphorus esters

JC Yang, DG Gorenstein

Index: Yang, Ji-Charng; Gorenstein, David G. Tetrahedron, 1987 , vol. 43, # 3 p. 479 - 486

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Citation Number: 20

Abstract

The rate of base catalyzed hydrolysis of cyclic five-membered ring 2-oxo-2-phenyl-1, 2- oxaphospholan, 1, and 2-oxo-2-phenyl-1, 3, 2-dioxaphospholan, 2, and their acyclic analogues ethyl ethylphenylphosphinate, 3, and diethyl phenylphosphonate, 4, were measured. The cyclic ester 1 hydrolyzes 6.2× 103 times faster than 3, corresponding to an activation free energy difference of 5.2 kcal Mol. This provides a good estimate of the ...