D. Kreher
Functionalisation reactions of 2,5-diphenyl-1,3,4-oxadiazoles bearing a terminal ethynyl or butadiynyl substituent: X-ray crystal structures of the products
Kreher, D.; Batsanov, A.S.; Wang, C.S.; Bryce, M.R.
Abstract
2-(4-tert-Butylphenyl)-5-(4-ethynylphenyl)-1,3,4-oxadiazole 1 and the butadiyne analogue 2 reacted with triethyl orthoformate in the presence of zinc iodide to give the acetal derivatives 3 and 4 which were hydrolysed with Amberlyst-15 in acetone-water to afford the alkynylaldehyde derivatives 5 and 6 in high yields. The reaction of 4,5-bis(methoxycarbonyl)-2-tributylphosphonium-1,3-dithiole tetra. uoroborate salt 7 with 5 (nBuLi, THF) gave the Wittig product 2-(3-{4-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl] phenyl} prop-2-ynylidene)-1,3-dithiole-4,5-dimethyl dicarboxylate 11 (33% yield) whereas other attempted Wittig and Horner - Wadsworth - Emmons reactions led to the unexpected loss of the aldehyde group from compounds 5 and 6 to give 1 and 2, respectively. The X-ray crystal structures of compounds 3, 4, 5 and 11 are reported: the pi-systems of all four molecules adopt predominantly planar conformations. A comparison of bond lengths in the structures of 5 and 11 reveals extended pi-conjugation in the latter.
Citation
Kreher, D., Batsanov, A., Wang, C., & Bryce, M. (2004). Functionalisation reactions of 2,5-diphenyl-1,3,4-oxadiazoles bearing a terminal ethynyl or butadiynyl substituent: X-ray crystal structures of the products. Organic and Biomolecular Chemistry, 2(6), 858-862
Journal Article Type | Article |
---|---|
Publication Date | 2004 |
Journal | Organic and Biomolecular Chemistry |
Print ISSN | 1477-0520 |
Electronic ISSN | 1477-0539 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 2 |
Issue | 6 |
Pages | 858-862 |
Public URL | https://durham-repository.worktribe.com/output/1601800 |
You might also like
Oligo(fluorenyl)pyridine ligands and their iridium complexes: Synthesis, photophysical properties and electrophosphorescent devices
(2005)
Presentation / Conference Contribution
Downloadable Citations
About Durham Research Online (DRO)
Administrator e-mail: dro.admin@durham.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2024
Advanced Search