Preparation of benzo- and polybenzocrown ethers by macrocyclization reactions

Abstract

Macrocyclization of crown ethers and their methods of preparation were explored. We present a robust, scalable method for the preparation of these macrocycles. Additionally, the effect of changing the structures of the precursors was explored to determine whether the ‘cut’ of bisphenol and dimesylate influenced the course of the reaction as measured by the yield. Further, using catechol derivatives, the method was used for the preparation of monobenzocrown ethers. Interestingly, for the preparation of monobenzocrown ethers, [2+2] adducts were discovered to be significantly contaminating the products. Dimesylates were chosen as the leaving group due to their ease or preparation and the ability to use the unpurified products with no apparent impact on the macrocyclization.