title: Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene.
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.
authors: School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
authors: Laurence
authors: L
authors: Burroughs
authors: School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
authors: John
authors: J
authors: Ritchie
authors: School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
authors: Mkhethwa
authors: M
authors: Ngwenya
authors: School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
authors: Dilfaraz
authors: D
authors: Khan
authors: School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
authors: William
authors: W
authors: Lewis
authors: School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
authors: Simon
authors: S
authors: Woodward
keywords: X-ray structures; allenes; anionic Chugaev rearrangement; anionic sigmatropic rearrangement; tetracene properties