2-(2,2-Dibromo­ethen­yl)thio­phene

The title compound, C(6)H(4)Br(2)S, represents a versatile building block for the preparation of π-conjugated redox-active thienyl oligomers and metal-mediated cross-coupling reactions. This is due to the presence of an electrochemically active thienyl heterocycle and a reactive dibromo­vinyl substi...

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Detalles Bibliográficos
Autores principales: Clément, Sebastien, Guyard, Laurent, Knorr, Michael, Eckert, Prisca K., Strohmann, Carsten
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3051600/
https://www.ncbi.nlm.nih.gov/pubmed/21523138
http://dx.doi.org/10.1107/S1600536811002522
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author Clément, Sebastien
Guyard, Laurent
Knorr, Michael
Eckert, Prisca K.
Strohmann, Carsten
author_facet Clément, Sebastien
Guyard, Laurent
Knorr, Michael
Eckert, Prisca K.
Strohmann, Carsten
author_sort Clément, Sebastien
collection PubMed
description The title compound, C(6)H(4)Br(2)S, represents a versatile building block for the preparation of π-conjugated redox-active thienyl oligomers and metal-mediated cross-coupling reactions. This is due to the presence of an electrochemically active thienyl heterocycle and a reactive dibromo­vinyl substituent, which easily undergoes dehydro­bromination in the presence of n-butyl­lithium to afford 2-ethynyl­thio­phene. In the molecule, the alkenyl unit and the thio­phene ring are almost coplanar with an angle of 3.5 (2)° between the normals of the best planes of the thio­phene ring and the vinyl moiety.
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spelling pubmed-30516002011-04-26 2-(2,2-Dibromo­ethen­yl)thio­phene Clément, Sebastien Guyard, Laurent Knorr, Michael Eckert, Prisca K. Strohmann, Carsten Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(6)H(4)Br(2)S, represents a versatile building block for the preparation of π-conjugated redox-active thienyl oligomers and metal-mediated cross-coupling reactions. This is due to the presence of an electrochemically active thienyl heterocycle and a reactive dibromo­vinyl substituent, which easily undergoes dehydro­bromination in the presence of n-butyl­lithium to afford 2-ethynyl­thio­phene. In the molecule, the alkenyl unit and the thio­phene ring are almost coplanar with an angle of 3.5 (2)° between the normals of the best planes of the thio­phene ring and the vinyl moiety. International Union of Crystallography 2011-01-22 /pmc/articles/PMC3051600/ /pubmed/21523138 http://dx.doi.org/10.1107/S1600536811002522 Text en © Clément et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Clément, Sebastien
Guyard, Laurent
Knorr, Michael
Eckert, Prisca K.
Strohmann, Carsten
2-(2,2-Dibromo­ethen­yl)thio­phene
title 2-(2,2-Dibromo­ethen­yl)thio­phene
title_full 2-(2,2-Dibromo­ethen­yl)thio­phene
title_fullStr 2-(2,2-Dibromo­ethen­yl)thio­phene
title_full_unstemmed 2-(2,2-Dibromo­ethen­yl)thio­phene
title_short 2-(2,2-Dibromo­ethen­yl)thio­phene
title_sort 2-(2,2-dibromo­ethen­yl)thio­phene
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3051600/
https://www.ncbi.nlm.nih.gov/pubmed/21523138
http://dx.doi.org/10.1107/S1600536811002522
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AT guyardlaurent 222dibromoethenylthiophene
AT knorrmichael 222dibromoethenylthiophene
AT eckertpriscak 222dibromoethenylthiophene
AT strohmanncarsten 222dibromoethenylthiophene

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