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-C(6)H(4)(CHO)(2) undergo cascades to tetracenes on simple admixture of LiHDMS, CS(2) and MeI. Acene formation proceeds by [3,3]-sigmatropic rearrangement of xanthate anions followed by 6π electro...

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Autores principales: Burroughs, Laurence, Ritchie, John, Ngwenya, Mkhethwa, Khan, Dilfaraz, Lewis, William, Woodward, Simon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362017/
https://www.ncbi.nlm.nih.gov/pubmed/25815080
http://dx.doi.org/10.3762/bjoc.11.31
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author Burroughs, Laurence
Ritchie, John
Ngwenya, Mkhethwa
Khan, Dilfaraz
Lewis, William
Woodward, Simon
author_facet Burroughs, Laurence
Ritchie, John
Ngwenya, Mkhethwa
Khan, Dilfaraz
Lewis, William
Woodward, Simon
author_sort Burroughs, Laurence
collection PubMed
description 1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C(6)H(4)(CHO)(2) undergo cascades to tetracenes on simple admixture of LiHDMS, CS(2) 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.
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spelling pubmed-43620172015-03-26 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 Beilstein J Org Chem Full Research Paper 1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C(6)H(4)(CHO)(2) undergo cascades to tetracenes on simple admixture of LiHDMS, CS(2) 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. Beilstein-Institut 2015-02-20 /pmc/articles/PMC4362017/ /pubmed/25815080 http://dx.doi.org/10.3762/bjoc.11.31 Text en Copyright © 2015, Burroughs et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Burroughs, Laurence
Ritchie, John
Ngwenya, Mkhethwa
Khan, Dilfaraz
Lewis, William
Woodward, Simon
Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
title Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
title_full Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
title_fullStr Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
title_full_unstemmed Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
title_short Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
title_sort anionic sigmatropic-electrocyclic-chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4362017/
https://www.ncbi.nlm.nih.gov/pubmed/25815080
http://dx.doi.org/10.3762/bjoc.11.31
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