Synthesis of Fluoroalkyl Vinyl Sulfoxides and their Use in Diels-Alder Reactions

Abstract

Condensation of various dienes with fluoroalkyl vinyl sulfoxides was studied. Four diastereoisomers were obtained in the case of cyclopentadiene and their structures were assigned by 2D NMR experiments. Diels-Alder cycloaddition occurred with cyclohexadiene, in comparison to phenyl vinyl sulfoxide, without thermal extrusion of fluoroalkylsulfenic acid. Condensation with anthracene led to a mixture of compounds 11 and 12.

acetylene equivalent - Diels-Alder reactions - eliminations - fluorine - sulfoxides

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