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Synthesis of New Resorcinarenes Under Alkaline Conditions

✍ Scribed by Jean-Marc Bourgeois; Helen Stoeckli-Evans

Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
124 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The preparation of functionalized resorcinarenes is described. Thus, 2‐nitroresorcinol (= 2‐nitrobenzene‐1,2‐diol), 2‐acetylresorcinol (= 1‐(2,6‐dihydroxyphenyl)ethanone), and 2,6‐dihydroxybenzoic acid were treated with formaldehyde in alkaline medium to give the corresponding resorcinarenes 1–3 (Scheme 1). This method is also applicable for resorcinol (= benzene‐1,3‐diol) itself, but the yields are poorer. In this case, the molecule formed is the simplest resorcinarene 4 on which a number of substituents can be inserted between the two OH groups. Thus, bromation of 4 yields 5 (Scheme 2). Some properties and conformations of these new products are discussed, and the X‐ray crystal structures of the nitro and bromo compounds 1 and 5, respectively, are presented.

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