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Synthesis and properties of 1,6-difunctionalized cyclodeca-3,8-diynes

The reaction of tert-butyl acetate (6) with 1,4-dibromobut-2-yne (1) in the presence of LDA yielded 1,6-di(tert-butyl)cyclodeca-3,8-diyne-1,6-dicarboxylate (8). The 1,6-di(tert-butyl) groups of 8 were transferred to bis(hydroxymethyl) (5), bis(bromomethyl) (13), bis(cyanomethyl) (14), dicarbaldehyde...

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Main Authors: Rajesh, Sheela (Author) , Haberhauer, Gebhard (Author) , Feuerbacher, Sven (Author) , Rominger, Frank (Author) , Oeser, Thomas (Author) , Gleiter, Rolf (Author)
Format: Article (Journal)
Language:English
Published: 19. Februar 2003
In: Synthesis
Year: 2003, Issue: 3, Pages: 0431-0435
ISSN:1437-210X
DOI:10.1055/s-2003-37347
Online Access:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1055/s-2003-37347
Verlag, lizenzpflichtig, Volltext: http://www.thieme-connect.de/DOI/DOI?10.1055/s-2003-37347
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Author Notes:Sheela Kochuparambil Chellappan, Gebhard Haberhauer, Sven Feuerbacher, Frank Rominger, Thomas Oeser, Rolf Gleiter

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520 |a The reaction of tert-butyl acetate (6) with 1,4-dibromobut-2-yne (1) in the presence of LDA yielded 1,6-di(tert-butyl)cyclodeca-3,8-diyne-1,6-dicarboxylate (8). The 1,6-di(tert-butyl) groups of 8 were transferred to bis(hydroxymethyl) (5), bis(bromomethyl) (13), bis(cyanomethyl) (14), dicarbaldehyde (15) and bis(methoxyvinyl) (16) groups. In case of 13 the two diastereomers [cis(a,e), trans(a,a)] were separated. From 13(a,e) and 14(a,a) we were able to obtain detailed structural parameters by means of X-ray crystallography. By means of temperature dependent NMR spectroscopy of 14(a,a) we estimated the activation energy for the chair-boat conversion to be 10.5 kcal/mol. 
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