4-Bromo-2-sulfolenes. Butadienyl Cation Equivalents

Article abstract of DOI:10.1021/jo00391a042

4-Bromo-2-sulfolene and 4-bromo-3-methyl-2-sulfolene react with alkylcuprates to give direct substitution products, with vinyl- or phenylcuprates or sulfur-containing nucleophiles to give allylic substitution products, and with strongly basic nucleophiles to give elimination products.The allylic substitution products and the isomerized direct substitution products are precursors for substituted 1,3-butadienes.Thus, these 4-bromo-2-sulfolenes serve as butadienyl cation equivalents.