Pure and Applied Chemistry

Abstract: A variety of aryleneethynylenes are synthesized by double elimination reaction of β-substituted sulfones. The acetylenic bond is formed from readily available aromatic aldehydes and benzylic sulfones. A sequence of aldol reaction, trapping of the aldolates with a leaving group, and eliminations proceeds in one pot. The utility of this protocol is exemplified by synthesis of dihalo diphenylacetylenes, 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene, and double-helical aromatic acetylenes.