Laurence Burroughs
Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
Burroughs, Laurence; Ritchie, John; Ngwenya, Mkhethwa; Khan, Dilfaraz; Lewis, William; Woodward, Simon
Authors
John Ritchie
Mkhethwa Ngwenya
Dilfaraz Khan
William Lewis
SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry
Abstract
1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C6H4(CHO)2 undergo cascades to tetracenes on simple admixture of LiHDMS, CS2 and MeI. Acene formation proceeds by [3,3]-sigmatropic rearrangement of xanthate anions followed by 6π electrocyclisations. The reactions are terminated by E2 or anionic Chugaev-type eliminations. Structural packing motifs and electronic properties are reported for the tetracenes.
Citation
Burroughs, L., Ritchie, J., Ngwenya, M., Khan, D., Lewis, W., & Woodward, S. (2015). Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene. Beilstein Journal of Organic Chemistry, 11, https://doi.org/10.3762/bjoc.11.31
Journal Article Type | Article |
---|---|
Acceptance Date | Jan 30, 2015 |
Publication Date | Feb 20, 2015 |
Deposit Date | Sep 28, 2017 |
Publicly Available Date | Sep 28, 2017 |
Journal | Beilstein Journal of Organic Chemistry |
Print ISSN | 1860-5397 |
Electronic ISSN | 1860-5397 |
Publisher | Beilstein-Institut |
Peer Reviewed | Peer Reviewed |
Volume | 11 |
DOI | https://doi.org/10.3762/bjoc.11.31 |
Keywords | allenes; anionic Chugaev rearrangement; anionic sigmatropic rearrangement; tetracene properties; X-ray structures |
Public URL | https://nottingham-repository.worktribe.com/output/744615 |
Publisher URL | http://www.beilstein-journals.org/bjoc/articles/11/31 |
Contract Date | Sep 28, 2017 |
Files
1860-5397-11-31.pdf
(871 Kb)
PDF
Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0
Downloadable Citations
About Repository@Nottingham
Administrator e-mail: discovery-access-systems@nottingham.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