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Issue 2, 2000
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A short survey of bicyclic diamines  syntheses and properties of N,N′-bridged-1,10-diazabicyclooctadeca-5,14-diynes

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Abstract

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, 3447, 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.

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Publication details

The article was received on 20 Sep 1999, accepted on 12 Nov 1999 and first published on 14 Jan 2000


Article type: Paper
DOI: 10.1039/A907609C
J. Chem. Soc., Perkin Trans. 2, 2000, 175-183

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

    T. von Hirschheydt, V. Wolfart, R. Gleiter, H. Irngartinger, T. Oeser, F. Rominger and F. Eisenträger, J. Chem. Soc., Perkin Trans. 2, 2000, 175
    DOI: 10.1039/A907609C

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