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Cyclic trimers and tetramers with piperazine and 2-butyne as building blocks

The reaction of piperazine with 2-butyne-1,4-ditosylate in a 1:1 ratio yields the cyclic trimer 7 and the cyclic tetramer 8. 1H NMR investigations on 7 and 8 reveal a dynamic process with ΔG‡ = 13 kcal/mol. This process is attributed to an inversion of the piperazine rings. Single crystals of 7·CH3O...

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Bibliographic Details
Main Authors: Gleiter, Rolf (Author) , Hövermann, Kirstin (Author) , Rominger, Frank (Author) , Oeser, Thomas (Author)
Format: Article (Journal) Festschrift
Language:English
Published: 22 January 2001
In: European journal of organic chemistry
Year: 2001, Issue: 4, Pages: 725-728
ISSN:1099-0690
DOI:10.1002/1099-0690(200102)2001:4<725::AID-EJOC725>3.0.CO;2-I
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Festschrift
Online Access:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/1099-0690(200102)2001:4<725::AID-EJOC725>3.0.CO;2-I
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200102%292001%3A4%3C725%3A%3AAID-EJOC725%3E3.0.CO%3B2-I
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Author Notes:Rolf Gleiter, Kirstin Hövermann, Frank Rominger, and Thomas Oeser
Description
Summary:The reaction of piperazine with 2-butyne-1,4-ditosylate in a 1:1 ratio yields the cyclic trimer 7 and the cyclic tetramer 8. 1H NMR investigations on 7 and 8 reveal a dynamic process with ΔG‡ = 13 kcal/mol. This process is attributed to an inversion of the piperazine rings. Single crystals of 7·CH3OH, 7·2 CF3COOH·H2O and 8 have been isolated and investigated by X-ray diffraction. In the first two cases methanol, or water and CF3CO2−, were included in the interior of the ring.
Item Description:Dedicated to Professor Richard Neidlein on the occasion of his 70th birthday
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Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/1099-0690(200102)2001:4<725::AID-EJOC725>3.0.CO;2-I

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