Synthesis and chemical properties of polyacetylenic derivatives of benzo-and dibenzo- crown ethers

Abstract

4′,5′-Diethynylbenzo-15-crown-5- (6), 4′, 5′(5″)-diethynyldibenzo-18-crown-6 (10, 11) and 4′,5′, 4″,5″-tetraethynyl-dibenzo-18-crown-6 (12) ethers were synthesized by cross-coupling of the corresponding di- and tetra- iodides (1-4) with trimethylsilylacetylene (5a) or 2-methylbut-3-yn-2-ol (5c) followed by treatment of the resulting products with alkali. The Mannich reaction with the di- and tetraethynyl derivatives was also carried out.