Reactivity of mesylates in dimethyl sulfoxide

CHED 851

Annette L Kohl, Department of Chemistry and Physics, Saint Marys College, Notre Dame, IN 46556 and Xavier Creary, Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, 46556.
Dimethyl sulfoxide is an aprotic polar solvent, but certain reactions seem to react via a carbocation in this solvent. The reactivity of &alpha-keto mesylates was studied in dimethyl sulfoxide. It is hypothesized that these compounds, although they react through a carbocation intermediate in protic solvents, do not react through a carbocation intermediate in dimethyl sulfoxide.