Rates and Mechanisms of Hydrolysis of Esters of Phosphorous Acid

Article abstract of DOI:10.1021/ja00209a029

Trialkyl phosphites hydrolyze in alkali several hudred times as fast as do the corresponding phosphates; in acid, however, the phosphite hydrolyzes 1E12 times asa fast as the phosphate.Dialkyl phosphites (i.e., dialkyl hydrogen phosphonates) hydrolyze in alkali more than 1E5 times as fast as do the corresponding triesters, presumably by way of metaphosphites as intermediates.The mechanisms of these various processes are discussed.The date are of interest in connection with the phosphite syntheses of DNA.