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

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 6? 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