Syntheses and structural properties of 1,8-diazacyclotetradeca-3,5,10,12-tetraynes
The syntheses of 1,8-diazacyclotetradeca-3,5,10,12-tetrayne (2a), its N,N′-dimethyl (2b), N,N′-diethyl (2c), N,N′-diisopropyl (2d), N,N′-diallyl (2e), and N,N′-dibenzyl (2f) derivatives were achieved in a one-pot procedure from primary amines and 1,6-dibromo-2,4-hexadiyne (4). Diffraction studies on...
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| Hauptverfasser: | , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
15 June 2000
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| In: |
European journal of organic chemistry
Year: 2000, Heft: 12, Pages: 2291-2294 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/1099-0690(200006)2000:12<2291::AID-EJOC2291>3.0.CO;2-U |
| Online-Zugang: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/1099-0690(200006)2000:12<2291::AID-EJOC2291>3.0.CO;2-U Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200006%292000%3A12%3C2291%3A%3AAID-EJOC2291%3E3.0.CO%3B2-U 
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| Verfasserangaben: | Kirstin Hövermann, Joachim Ritter, Frank Rominger, Bernhard Nuber, and Rolf Gleiter |
| Zusammenfassung: | The syntheses of 1,8-diazacyclotetradeca-3,5,10,12-tetrayne (2a), its N,N′-dimethyl (2b), N,N′-diethyl (2c), N,N′-diisopropyl (2d), N,N′-diallyl (2e), and N,N′-dibenzyl (2f) derivatives were achieved in a one-pot procedure from primary amines and 1,6-dibromo-2,4-hexadiyne (4). Diffraction studies on single crystals of 2c−2f reveal a chair conformation with the substituents in the diaxial positions. The preference of the axial orientation of the substituents on the nitrogens in 2c−2f is due to several contributions: minimal synaxial 1,3 interactions of the NR bond and the lone pair with adjacent CH and CC bonds. |
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| Beschreibung: | Gesehen am 27.10.2020 |
| Beschreibung: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/1099-0690(200006)2000:12<2291::AID-EJOC2291>3.0.CO;2-U |