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Synthesis and conformational analysis of a small meta-cyclophane, bis(5-carbomethoxy-1,3-phenylene)-14-crown-4

✍ Scribed by Harry W. Gibson; Hong Wang; Chin P. Chng; Thomas E. Glass; Daniel Schoonover; Lev N. Zakharov; Arnold L. Rheingold

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 336 KB
Volume: 19
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20393

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✦ Synopsis

Abstract

A small cyclophane, bis(5‐carbometh‐oxy‐1,3‐phenylene)‐14‐crown‐4 (BCMP14C4, 3) and its diacid, bis(5‐carboxy‐1,3‐phenylene)‐14‐crown‐4 (4), were synthesized and characterized. The solid‐state molecular structures of 3 and 4 were determined by X‐ray crystallography as ladder or stepped conformations in which the two aromatic rings are antiparallel to each other without overlap and the ethylene tethers both take trans‐conformations. Diester 3 is formed in the lowest cyclization yield (under the same reaction conditions) and exhibits the highest melting point compared to its larger ring (20‐, 26‐ and 32‐membered) analogs. In CD~2~Cl~2~ solution, diester 3 exists predominantly as a nonplanar gauche–gauche structure as deduced by H NMR studies. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:48–54, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20393

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