Molecular Rods: Facile Desymmetrization of 1,4-Diethynylbicyclo[2.2.2]octane

Abstract

We report a facile desymmetrization of 1,4-diethynylbicyclo[2.2.2]octane. One of the acetylene termini was protected by TMS and the desired product was purified by sublimation.

It is stable but reactive, as shown by the synthesis of a complex pyridine-terminated molecular rod containing both a bicyclo[1.1.1]pentane and a bicyclo[2.2.2]octane cage. Six crystal structures of key intermediates are presented.

Keywords

• fused-ring systems
• supramolecular chemistry
• molecular rods
• alkynes