Synthesis and reactions of 2-SF5-butadiene

A stable and storable precursor of 2-SF5-butadiene, 3-SF5-3-sulfolene, has been synthesized and its reactivity studied with several olefinic compounds. When SF5Br is added to sulfolene, 3-bromo-4-SF5-sulfolane is formed and when reacted further with silver tosylate forms 4-SF5-2-sulfolene. The 4-SF5-2-sulfolene undergoes rearrangement with silicic acid to give 3-SF5-3-sulfolene and when heated forms 2-SF5-butadiene; in the absence of a dienophile, dimerization does occur. The new 2-SF5-butadiene is a reactive diene undergoing a Diels–Alder reaction with olefinic sytems such as maleic anhydride, p-naphthoquinone, and methyl acrylate.