Synthesis of oxaquinonacyclophanes from bromobenzoquinones

In the Wackerly Lab, we focus on the synthesis and characterization of polyarylether macrocycles known as [1n]oxacyclophanes. These compounds may have the ability to act as supramolecular host molecules much like (2-hydroxypropyl)-�-cyclodexterin, the active ingredient of Febreze, acts as a host molecule for stinky small molecules. This presentation will describe our efforts towards the synthesis of macrocycles where some of the benzene rings have been replaced by quinone rings. To this end we have synthesized or purchased bromobenzoquinone electrophilies and investigated their addition-elimination chemistry with oxygen nucleophiles.