Reactions of fluorinated cyclobutenes with grignard reagents

Abstract

The reaction of an alkylmagnesium bromide with perfluorocyclobutene has been found to favor the formation of a vinylic monoalkyl product whereas an alkylmagnesium chloride favored the synthesis of a vinylic dialkyl compound. Increased branching at the α- or β-carbon of the isomeric butyl Grignard reagents caused a shift to the vinylic monoalkyl product and to reduced yields, especially with increased α-branching. Unsymmetrical vinylic dialkylperfluorocyclobutenes are reported for the first time.