1,8-diazabicyclo(6.6.6)eicosane, 1,8-diazabicyclo(6.6.5)nonadecane and 1,8-diazabicyclo(6.6.4)octadecane and their diprotonated forms
The preparation of the title compounds 9−11 was achieved by catalytic hydrogenation of 1,8-diazabicyclo[6.6.6]eicosa-4,11-diyne (13), 1,8-diazabicyclo[6.6.5]nonadeca-4,11-diyne (14), and 1,8-diazabicyclo[6.6.4]octadeca-4,11-diyne (15), respectively. As catalyst we used Pd(OH)2 on carbon. NMR studies...
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| Hauptverfasser: | , , , , , |
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| Dokumenttyp: | Article (Journal) Festschrift |
| Sprache: | Englisch |
| Veröffentlicht: |
15 June 2004
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| In: |
European journal of organic chemistry
Year: 2004, Heft: 13, Pages: 2812-2817 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200400058 |
| Schlagworte: | |
| Online-Zugang: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.200400058 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200400058 
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| Verfasserangaben: | Brett Pool, Saeed Balalaie, Andreas Kunze, Gerhard Schilling, Peter Bischof, and Rolf Gleiter |
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| 500 | |a Im Titel steht 6.6.6, 6.6.5 und 6.6.4 jeweils in eckiger Klammer | ||
| 500 | |a Dedicated to Professor Zvonimir B. Maksić on the occasion of his 65th birthday | ||
| 500 | |a Gesehen am 27.10.2020 | ||
| 520 | |a The preparation of the title compounds 9−11 was achieved by catalytic hydrogenation of 1,8-diazabicyclo[6.6.6]eicosa-4,11-diyne (13), 1,8-diazabicyclo[6.6.5]nonadeca-4,11-diyne (14), and 1,8-diazabicyclo[6.6.4]octadeca-4,11-diyne (15), respectively. As catalyst we used Pd(OH)2 on carbon. NMR studies on 9−11 revealed an in/in conformation at the bridgehead positions. Treatment of 9−11 with an excess of trifluoroacetic acid yielded, in a kinetically controlled reaction, mixtures of the out/out and in/out diprotonated species [9·2H]2+, [10·2H]2+ and [11·2H]2+. The thermodynamically controlled species, the corresponding in/in conformers, are formed at higher temperatures and longer reaction times. The experimental observations are supported by AM1 calculations. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) | ||
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