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Formation of hybrid polymethylene-poly(oxyethylene) macrocycles

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Maclocyclisations, particularly those forming crown ethers, normally require high dilution conditions. However, treatment of 1,9-bis(sarcosylamino)nonane with alpha,omega -bis(oxiranylmethyl) ethers derived from oligomeric poly(ethyleneglycol)s of MW 400-600 Da under high concentration conditions was found to give excellent yields of 1:1 hybrid polymethylene-poly(oxyethylene) 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, GPC and MS. (C) 2001 Elsevier Science Ltd. All rights reserved.

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