Double elimination protocol for aryleneethynylenes*
Junzo Otera
Department of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan
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.
Keywords: double elimination; aryleneethynylenes; β-substituted sulfones; dihalo diphenylacetylenes; tetradehydrodibenzo[a,e]cyclooctene; double-helical aromatic acetylenes.
*Paper based on a presentation at the 11th International Symposium on Novel Aromatic Compounds (ISNA-11), St. John's, Newfoundland, Canada, 14-18 August 2005. Other presentations are published in this issue, pp. 685-888..