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A short survey of bicyclic diamines-syntheses and properties of N,N′-bridged-1,10-diazabicyclooctadeca-5,14-diynes

The conformations and properties of 1,(k + 2)-diazabicyclo[k.l.m]alkanes are reviewed briefly. In these species the alkane chains allow inside protonation but no metal complexation. Inside metal complexation is made possible if the alkane chains incorporate alkyne units. The preparation and structur...

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Main Authors: Hirschheydt, Thomas von (Author) , Wolfart, Volker (Author) , Gleiter, Rolf (Author) , Irngartinger, Hermann (Author) , Oeser, Thomas (Author) , Rominger, Frank (Author) , Eisenträger, Frank (Author)
Format: Article (Journal)
Language:English
Published: 14th January 2000
In: Perkin
Year: 2000, Issue: 2, Pages: 175-183
ISSN:1364-5471
DOI:10.1039/A907609C
Online Access:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1039/A907609C
Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2000/p2/a907609c
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Author Notes:Thomas von Hirschheydt, Volker Wolfart, Rolf Gleiter, Hermann Irngartinger, Thomas Oeser, Frank Rominger and Frank Eisenträger
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Summary:The conformations and properties of 1,(k + 2)-diazabicyclo[k.l.m]alkanes are reviewed briefly. In these species the alkane chains allow inside protonation but no metal complexation. Inside metal complexation is made possible if the alkane chains incorporate alkyne units. The preparation and structures of bridged 1,10-diazacyclooctadeca-5,14-diynes are reported. As bridges we use simple alkyl chains from (CH2)2 to (CH2)10, di- and triethyleneglycol, but-2-yne, hex-3-yne, and oct-4-yne chains. The resulting bicyclic systems, 34-47, adopt in the solid state either the in/in or the out/out conformations. By means of dynamic NMR spectroscopy a homeomorphic isomerism in 34 was uncovered. A second dynamic process, a “wagging” motion of the alkyne bridges, could be studied in case of 35. The molecular dimensions in the solid state reveal N⋯N distances between 3.16 Å and 6.52 Å. The intramolecular distances between the triple bonds vary between 4.25 Å and 7.31 Å.
Item Description:Gesehen am 04.11.2020
Physical Description:Online Resource
ISSN:1364-5471
DOI:10.1039/A907609C

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