Premium
Synthesis of New Resorcinarenes Under Alkaline Conditions
Author(s) -
Bourgeois JeanMarc,
StoeckliEvans Helen
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590211
Subject(s) - chemistry , resorcinarene , nitrobenzene , resorcinol , formaldehyde , nitro , diol , molecule , benzene , medicinal chemistry , organic chemistry , stereochemistry , catalysis , alkyl
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.