The Journal of Organic Chemistry

Reaction of diazonium salts with nucleophiles. XVIII. Dimethyl phosphonate in base

ES Lewis, EC Nieh

Index: Lewis,E.S.; Nieh,E.C. Journal of Organic Chemistry, 1973 , vol. 38, p. 4402 - 4404

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Citation Number: 5

Abstract

The rates of reaction of diazonium salts with dimethyl phosphonate have been followed in two cases. The kinetics, almost but not exactly third order, indicate that the ionization of dimethyl phosphonate by base occurs before the attack of diazonium salt on the phosphonate anion, but neither step is rate determining at accessible concentrations. Most of the isolated arylazophosphonates probably have syn stereochemistry.