Resorcinarenes as Templates

Abstract Metal ions are superb at templating the synthesis of small macrocycles that are decorated with Lewis basic sites. However, for the synthesis of larger macrocycles, or the synthesis of macrocycles devoid of an array of Lewis basic sites, metal ions are less useful. Here we demonstrate that resorcinarenes can be used as templates to engender the efficient formation of large crown ethers. A three step process of 1) tethering moieties to the template, 2) linking those moieties, and 3) then cleaving off the template leads to the efficient formation of a family of aromatic crown ethers. If adaptable, this approach will prove useful for the construction of macrocycles that are hard to obtain from a step-wise synthesis.