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Synthesis and characterization of new crown-type compounds with 4-pyrone Units

✍ Scribed by Werner Löwe; Stefanie Brätter; Christoph Dietrich; Manuela Weber; Peter Luger

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
444 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

We report here the syntheses and characterization of new crown‐type compounds 8 and 9 incorporated with one and two 4‐pyrone units. The reaction of compound 3 with 1,5‐bis(2‐hydroxyphenoxy)‐3‐oxapentane or catechol gave the desired molecules 8 and 9 in 65% and 25% yields, respectively. Compound 3 resulted from 1 by Wohl‐Ziegler bromination in small amounts and could be separated from five bromination by‐products by column chromatography. For example, 8 binds K^+^ and a pyrylium salt 11 (single crystal X‐ray structure analysis) can also be prepared starting from 3 by treatment of the latter with perchloric acid in the presence of acetonitrile.

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