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Molecular Receptors. Functionalized and chiral macrocyclic polyethers derived from tartaric acid
Author(s) -
Behr JeanPaul,
Girodeau JeanMarc,
Hayward Rodney C.,
Lehn JeanMarie,
Sauvage JeanPierre
Publication year - 1980
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.19800630736
Subject(s) - chemistry , tartaric acid , cationic polymerization , condensation , catalysis , stereochemistry , molecule , combinatorial chemistry , polymer chemistry , organic chemistry , physics , citric acid , thermodynamics
A number of functionalized and chiral macrocyclic polyethers have been synthesized by condensation of the dithallium alcoholate of ( R,R )‐(+)‐tartaric acid derivatives with α, ω‐dihalides. In this way for instance, the tetracarboxylic [18]‐O 6 macrocycle 3c and its derivatives become readily available. They form complexes with various cationic substrates. NMR. and crystal‐structure data provide information about the orientation of the side chains X in 3 with respect to the macrocycle. It is concluded that in the secondary amides like 3b and in their complexes the four X‐groups are preferentially in an axial orientation on the average. This property is of much significance for the design of molecular receptors and catalysts based on this macrocyclic structure. The preparation of a number of other macrocycles is also described.