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Preparation and Reaction of Tosylates

prep. of tosylates
substitution of tosylates

Reaction type: Nucleophilic Substitution (usually SN2)


This is the reagent used to prepare the tosylate ester. It maybe referred to by any of the terms shown. 
The tosylate ester is shown. Note that the oxygen atom from the original alcohol is retained.
In the reactions of tosylates, the displaced group is the resonance stabilised anion shown, which is a good leaving group.

Note that the preparation of the tosylate is similar to the reaction of an alcohol with thionyl chloride, SOCl2.

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© Dr. Ian Hunt, Department of Chemistry, University of Calgary