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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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
10 October 2006
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| In: |
European journal of organic chemistry
Year: 2006, Issue: 23, Pages: 5264-5278 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200600512 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/ejoc.200600512 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200600512/abstract 
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| Author Notes: | Martin Baier, Rolf Gleiter and Frank Rominger |
| Summary: | 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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| Item Description: | Gesehen am 29.09.2017 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200600512 |