Kosinski C, Hirsch A, Heinemann FW, Hampel F (2001)
Publication Type: Journal article, Original article
Publication year: 2001
Original Authors: Kosinski C., Hirsch A., Heinemann F.W., Hampel F.
Publisher: Wiley-VCH Verlag
Pages Range: 3879-3890
Journal Issue: 20
URI: https://www.scopus.com/record/display.uri?eid=2-s2.0-0034781028&origin=inward
Phenyl-terminated cis-oligodiacetylenes such as 18, containing a π-conjugated backbone with four triple and three double bonds, were synthesized using Pd-catalysed Sonogashira coupling reactions. Compound 18 represents the longest cis-oligoenyne system to date, but it suffers from the drawback of cis/trans isomerization observed in solution. In order to avoid cis/trans isomerization in such cis-oligodicacetylenes, the ene moieties within the oligomeric backbone were locked by incorporation into ring systems. 1,2-Dibromocyclopentene was used as an olefinic building block for this purpose, permitting the iterative synthesis of the cis-oligodiacetylenes 27 and 28, possessing the same π-conjugated backbone as 18. Unlike that compound, however, 27 and 28 are stable both in solution and in the solid state. Whereas X-ray crystallography revealed a completely planar structure for 27 in the single crystal, NMR and computational investigations suggest that a preferred helical conformation is likely in solution.
APA:
Kosinski, C., Hirsch, A., Heinemann, F.W., & Hampel, F. (2001). An iterative approach to cis-oligodiacetylenes. European Journal of Organic Chemistry, 20, 3879-3890.
MLA:
Kosinski, Christoph, et al. "An iterative approach to cis-oligodiacetylenes." European Journal of Organic Chemistry 20 (2001): 3879-3890.
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