Issue 11, 1981

Elimination–addition mechanisms of sulphonyl group transfer: evidence for a dicarbanionic intermediate in the alkaline hydrolysis of aryl methylsulphonylmethanesulphonate esters

Abstract

Kinetic evidence has been obtained from the hydrolysis of the title compounds that is consistent with a dissociative mechanism; ionization of the substrate is followed by the slow unimolecular breakdown of the conjugate base to phenoxide ion and sulphene, but at hight pH values a further ionizatio occurs to give a dicarbanion which undergoes E1-elimination of phenolate ion to yield a sulphene anion in the rate determining step.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1981, 535-536

Elimination–addition mechanisms of sulphonyl group transfer: evidence for a dicarbanionic intermediate in the alkaline hydrolysis of aryl methylsulphonylmethanesulphonate esters

S. Thea, G. Guanti and A. Williams, J. Chem. Soc., Chem. Commun., 1981, 535 DOI: 10.1039/C39810000535

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