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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

Laurence Burroughs

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 http://eprints.nottingham.ac.uk/id/eprint/46641
Publisher URL http://www.beilstein-journals.org/bjoc/articles/11/31
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





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