Glaser–Eglinton–Hay sp–sp coupling and macrocyclization: construction of a new class of polyether macrocycles having a 1,3-diyne unit

Abstract

Glaser-Eglinton-Hay-type sp-sp coupling, macrocyclization and the construction of skeletally interesting, 18-27 membered, polyether macrocycles having a 1,3-diyne unit-based cylindrical backbone are reported. The utility of polyether macrocycles having the 1,3-diyne units is shown by incorporating isoxazole and thiophene moieties into the macrocycles. The structures of representative crown ether/polyether-type macrocycles were unambiguously established from single crystal X-ray structure analyses. Investigation of the X-ray structures of representative macrocycles revealed that the 1,3-diyne unit was not linear and was found to be bent.