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Tripodands with phenyl and thiophenyl rings and nitrogen bridgehead atoms

The flexible tripodands 7-9 and 15 with phenyl and thiophenyl rings as “legs” and nitrogen as bridgehead atoms have been synthesized by three-component condensation reactions of the corresponding amine with the aryl halide. The more rigid species 10-14 and 17 were built up from the podands 7-9 as we...

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Hauptverfasser: Baier, Martin (VerfasserIn) , Gleiter, Rolf (VerfasserIn) , Rominger, Frank (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 10 October 2006
In: European journal of organic chemistry
Year: 2006, Heft: 23, Pages: 5264-5278
ISSN:1099-0690
DOI:10.1002/ejoc.200600512
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/ejoc.200600512
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200600512/abstract
Volltext
Verfasserangaben:Martin Baier, Rolf Gleiter and Frank Rominger

MARC

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520 |a The flexible tripodands 7-9 and 15 with phenyl and thiophenyl rings as “legs” and nitrogen as bridgehead atoms have been synthesized by three-component condensation reactions of the corresponding amine with the aryl halide. The more rigid species 10-14 and 17 were built up from the podands 7-9 as well as from their iodine substitution products 33-35 by a sequence of ethynylation and C-C coupling reactions. Podand 16 was prepared from tris-iodide 36 by Sonogashira coupling with phenylacetylene. In the cases of 7, 12, 15-17, 22, 24, 35, 36, and 41 the structural parameters were determined by X-ray studies. With the exception of 7, 12, and 17, all structures show either close intermolecular contacts between heteroatoms (15, 22, 24, 35, and 36), C-H···N hydrogen bonding (41), or are closely packed as a result of π···π stacking (16). We were able to isolate silver triflate complexes of 9, 10, and 16, and in the case of 9 we obtained crystals suitable for X-ray diffraction studies. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) 
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