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Calix[5]‐ and Calix[8]arenes Bridged with Heterocycles
Author(s) -
Konrad Serge,
Näther Christian,
Lüning Ulrich
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400774
Subject(s) - chemistry , pyridine , reagent , calixarene , phenanthroline , bridging (networking) , condensation , medicinal chemistry , polymer chemistry , cyclophane , organic chemistry , molecule , computer network , physics , computer science , thermodynamics
Abstract Calix[5]arene ( 2 ) and calix[8]arene ( 4 ) reacted with bis(bromomethyl)‐substituted heterocycles such as pyridine and 1,10‐phenanthroline to give [1+1] condensation products 10 and 16–18 (bridged bimacrocycles) and [2+1] dicalixarenes 11 , 13 and 14 , all of which were fully characterized. Although the bridging capability of both bridging units 5 and 6 is surprisingly similar, calix[5]arene ( 2 ) could only be bridged with the pyridine derivatives 5 . With calix[8]arene ( 4 ), the 1,10‐phenanthroline bridging reagent 6 gave a cleaner product spectrum than the pyridine reagent 5 . The 1,10‐phenanthroline‐bridged calix[8]arene 16 was characterized by X‐ray analysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)