Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene

Burroughs, Laurence and Ritchie, John and Ngwenya, Mkhethwa and Khan, Dilfaraz and Lewis, William and Woodward, Simon (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 . pp. 273-279. ISSN 1860-5397

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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.

Item Type: Article
Keywords: allenes; anionic Chugaev rearrangement; anionic sigmatropic rearrangement; tetracene properties; X-ray structures
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.3762/bjoc.11.31
Depositing User: Lewis, William
Date Deposited: 28 Sep 2017 12:10
Last Modified: 14 Oct 2017 08:29
URI: http://eprints.nottingham.ac.uk/id/eprint/46641

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