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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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Bibliographic Details
Main Authors: Pool, Brett (Author) , Balalaie, Saeed (Author) , Kunze, Andreas (Author) , Schilling, Gerhard (Author) , Bischof, Peter (Author) , Gleiter, Rolf (Author)
Format: Article (Journal) Festschrift
Language:English
Published: 15 June 2004
In: European journal of organic chemistry
Year: 2004, Issue: 13, Pages: 2812-2817
ISSN:1099-0690
DOI:10.1002/ejoc.200400058
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Festschrift
Online Access: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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Author Notes:Brett Pool, Saeed Balalaie, Andreas Kunze, Gerhard Schilling, Peter Bischof, and Rolf Gleiter
Description
Summary: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)
Item Description:Im Titel steht 6.6.6, 6.6.5 und 6.6.4 jeweils in eckiger Klammer
Dedicated to Professor Zvonimir B. Maksić on the occasion of his 65th birthday
Gesehen am 27.10.2020
Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.200400058

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