Original scientific paper

The Neighboring Sulfonium Group in Ester Hydrolysis. III

Joseph Casanova ; Department of Chemistry and Biochemistry, California State University, Los Angeles, Los Angeles California 90032, USA
Randolph Cooper ; Department of Chemistry and Biochemistry, California State University, Los Angeles, Los Angeles California 90032, USA
Edward J. Bahe ; Department of Chemistry and Biochemistry, California State University, Los Angeles, Los Angeles California 90032, USA
Kenneth L. Servis ; Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA

Abstract

Z- and E-2-carbomethoxy-3-(methylenedimethylsulfonio)-bicyclo- [2.2.2]octane p-toluenesulfonate (8z and 8e, respectively) were synthesized and saponified at constant pH to study the effect of the neighboring sulfonium group on the rate of reaction. Rates and activation parameters are very similar for both isomers, lending support to the theoretical prediction that charge-dipole and charge-charge separation in both isomers is not significantly different, and that the carbonyl-dipole vector is nearly normal to a line connecting it with the sulfonium sulfur atom.

Keywords

Hrčak ID:

135983

URI

https://hrcak.srce.hr/135983

Publication date:

2.12.1996.

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