The Synthesis of 2-Aryl-3-Fluoroalkoxy-1-Propenes and Some Potentially Useful Reaction of These Systems

This report discusses research involving the fluoroalkoxylation of 2-arylprop-1-en-3-yltrimethylammonium iodides and the useful synthetic application of the adducts formed. The present work includes: 1) reactions of several 2-arylprop-1-en-3-yltrimethylammonium iodides with the sodium salt of 2,2,2-trifluoroethanol; 2) reactions of several fluoroalkoxy alcohols with 2-(4-bromophenyl)prop-1-en-3-yltrimethylammonium iodide; and 3) the oxidation of 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethyoxy)-1-propene using the Lemieux/von Rudloff reagent. This report reveals the experimental conditions and procedures used as well as spectral and physical data of all new compounds synthesized. Explanation is offered for a possible mechanism for the formation of these compounds and recommendations for future research are given