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Chemical Modifications of Furan-Based Calixarenes by Diels–Alder Reactions

✍ Scribed by Grazia Cafeo; Marco Giannetto; Franz H. Kohnke; Giovanna L. La Torre; Melchiorre F. Parisi; Stephan Menzer; Andrew J. P. White; David J. Williams

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
363 KB
Volume
5
Category
Article
ISSN
0947-6539

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✦ Synopsis

The simple chemical modification by Diels ± Alder reactions of the cyclic hexamer of furan and acetone, utilising two readily accessible dienophiles, benzyne and dimethylacetylenedicarboxylate (DMAD), is described. The studies have explored the ease with which different furan units within the macrocycle can be converted into either naphthalenes, o-phthalic ester residues or 3,4-furandicarboxylate units. The cy-cloaddition products are shown to differ as a function of stoichiometry, regiochemistry and stereochemistry. The problems encountered in the attempts to aromatise the benzyne adducts to their corresponding naphthafurophanes hamper the exploitation of these compounds as acenophane precursors. Similarly, the DMAD adducts are not suitable precursors for derivatives containing phthalic acid units. On the other hand, they readily provide access to furanophanes containing carboxyl substituents. The X-ray crystal structures of a variety of key derivatives have been determined and their conformations analysed and compared.

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