Studies on Esters of Sulphuric Acid. I. Positions of Bond Fission during Hydrolysis of Dialkyl Sulyhates in Oxygen-18 Water

Abstract

The positions of bond fission during the first stage hydrolysis of dimethyl, diethyl, and di-isopropyl sulphates under acidic and alkaline conditions between 0 and 50 °C have been determined by the use of ¹⁸O-enriched water. Isotopic analysis by the two independent methods, namely, mass-spectrometry and micropyknometric density determination, agreed within experimental error. Each ester showed almost 100% alkyl-oxygen fission. R-i-O.SO₂.OR, under all conditions used. The present work establishes with reasonable certainty that the results of similar work by Kursanov and Kudryavtsev (1956) on dimethyl sulphate and of Anbar et al. (1954) on diethyl sulphate are in error.