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

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

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 electrocyclisat...

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Bibliographic Details
Main Authors: Laurence Burroughs, John Ritchie, Mkhethwa Ngwenya, Dilfaraz Khan, William Lewis, Simon Woodward
Format: Article
Language:English
Published: Beilstein-Institut 2015-02-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
allenes
anionic Chugaev rearrangement
anionic sigmatropic rearrangement
tetracene properties
X-ray structures
Online Access:https://doi.org/10.3762/bjoc.11.31

Internet

https://doi.org/10.3762/bjoc.11.31

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