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Novel Spherand‐Type Calixarenes – Synthesis, Conformational Studies, and Isomer Separation
Author(s) -
Yamato Takehiko,
Hasegawa KenIchi,
Saruwatari Yoshiyuki,
Doamekpor Louis Korbla
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260625
Subject(s) - chemistry , trimer , tetramer , calixarene , yield (engineering) , formaldehyde , cyclophane , condensation , xylene , stereochemistry , base (topology) , nmr spectra database , molecule , crystallography , organic chemistry , spectral line , benzene , dimer , materials science , physics , metallurgy , thermodynamics , enzyme , mathematical analysis , mathematics , astronomy
The novel macrocyclic compounds hexahydroxy[1.0.1.0.1.0]‐ 6b and octahydroxy[1.0.1.0.1.0.1.0]metacyclophane 6c have been prepared in 50–70% yield by base‐catalyzed condensation of 5,5′‐di‐ tert 1‐butyl‐2,2′‐dihydroxybiphenyl ( 5 ) with formaldehyde in xylene. The conformations of trimer 6b and tetramer 6c have been evaluated from their dynamic 1 H‐NMR spectra. Methylation of the hydroxyl groups of 6b and 6c with MeI gives the corresponding methoxy[1 n ]metabiphenylophanes 7b and 7c in good yields. The metacyclophane 7b has been found to consist of two isomers, out of which one was separated pure. The structural characterization of these products is discussed.