Formation of hybrid polymethylene-poly(oxyethylene) macrocycles

Maclocyclisations, particularly those forming crown ethers, normally requir e high dilution conditions. However, treatment of 1,9-bis(sarcosylamino)non ane with alpha,omega -bis(oxiranylmethyl) ethers derived from oligomeric po ly(ethyleneglycol)s of MW 400-600 Da under high concentration conditions wa s found to give excellent yields of 1:1 hybrid polymethylene-poly(oxyethyle ne) macrocyclic crown ether derivatives. The corresponding alpha,omega -bis (oxiranylmethyl) ether derived from poly(ethyleneglycol) of mean MW 1500 Da gave polymeric material only. The macrocycles were characterised by NMR, G PC and MS. (C) 2001 Elsevier Science Ltd. All rights reserved.