Sulfur-Oxygen Scission versus Carbon-Oxygen Scission in Reactions of 2, 4-Dinitrophenyl p-Toluenesulfonate and Related Esters with Nucleophilic Reagents1

JF Bunnett, JY Bassett Jr

Index: Bunnett; Bassett Journal of the American Chemical Society, 1959 , vol. 81, p. 2104,2108

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Citation Number: 43

Abstract

A number of inono-and dinitrophenyl esters of p-toluenesulfonic and mesitylenesulfonic acids have been found to undergo both sulfur-oxygen and carbon-oxygen scission in reactions with nucleophilic reagents. With 2, 4-dinitrophenyl p-toluenesulfonate, the fraction of C-0 scission varies according to the reagent used from 100yo with sodium thiophenoxide to hut 12y0 with sodium methoxide. The relative rates of C-0 and S-0 scission are not ...