Formation of huge cyclic oligomers in the condensation polymerization of bis (9-hydroxy-1, 4, 7-trioxanonyl) substituted naphthalene and benzenes with both aromatic …

…, EJ Vlietstra, A van der Kerk-van Hoof…

Index: Mertens, Ingrid J. A.; Wegh, Rene; Jenneskens, Leonardus W.; Vlietstra, Edward J.; Van Der Kerk-van Hoof, Anca; Zwikker, Jan W.; Cleij, Thomas J.; Smeets, Wilberth J. J.; Veldman, Nora; Spek, Anthony L. Journal of the Chemical Society. Perkin Transactions 2, 1998 , # 3 p. 725 - 736

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Abstract

Without the use of high dilution techniques condensation polymerization of bis (9-hydroxy-1, 4, 7-trioxanonyl) substituted naphthalene and benzenes (1a–d) with the bis-acid chlorides terephthaloyl dichloride (2), adipoyl dichloride (5a) and isophthaloyl dichloride (5b) at 80° C, respectively, gives giant-size macrocycles, ie crownophanes 3a (n) with n= 1–5, 3b–d (n) with n= 1–3 and 6a–b (n) with n= 1–2, respectively, in high overall yield (ca. 30% w/w, ...