Date of Award

Fall 1988

Degree Type

Thesis - Restricted

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Jache, Albert

Second Advisor

Cremer, Sheldon E.

Third Advisor

Hoffman, Norman E.

Abstract

Introduction of fluorine into organic molecules is important from the chemical and pharmaceutical point of view. There is only a limited number of reagents known that are able to introduce fluorine into organic molecules under mild conditions. Among these are: fluoroxytrifluoromethane, CF30F 1 ; fluoroxypentafluoroethane, CF3CF20F 2; trifluoroacetyl hypofluorite, CF3COOF 3; fluorine, F2 4 ; xenon difluoride, XeF2 5 ' 6 ; and acetyl hypofluorite, CH3COOF T-9. Cesium fluoroxysulfate has been recently prepared 11 and used to fluorinate various organic molecules 11-14,17-29. This investigation was directed to the study of the fluorination of toluene with cesium fluoroxysulfate in acetonitrile and the effect that water concentration, catalysts, and temperature had on this reaction. Another part of the project was a comparison on the different products obtained in the fluorination by either fluorine or cesium fluoroxysulfate of three organic compounds which can exist in their keto or enol form or that could act as ligands, namely ethyl acetoacetate, methyl acetoacetate, and dimethyl malonate.

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