Unprecedented Demonstration of Regioselective SE Ar Reaction giving Unsymmetrical Regioregular Oligothiophenes

Aromatization of 4-cyano-3-oxotetrahydrothiophene by sulfuryl chloride gives the new building block 4-cyano-3-pyrrolidylthiophene, which forms unsymmetrical regioregular oligothiophenes with a strict alternation of the donor and acceptor groups along the conjugated system. The self-coupling reaction...

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Bibliographic Details
Published in:	Chemistry : a European journal Vol. 22; no. 19; pp. 6510 - 6514
Main Authors:	Moussallem, Chady, Olivier, Simon, Grolleau, Jérémie, Allain, Magali, Mallet, Charlotte, Savitha, Gurunathan, Gohier, Frédéric, Frère, Pierre
Format:	Journal Article
Language:	English
Published:	Germany 04-05-2016
Subjects:	Molecular Structure Pyrrolidines - chemistry Stereoisomerism Thiophenes - chemistry regioselectivity thiophenes oligomerization organic synthesis electrophilic substitution
Online Access:	Get full text
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Summary:	Aromatization of 4-cyano-3-oxotetrahydrothiophene by sulfuryl chloride gives the new building block 4-cyano-3-pyrrolidylthiophene, which forms unsymmetrical regioregular oligothiophenes with a strict alternation of the donor and acceptor groups along the conjugated system. The self-coupling reactions that form the oligomers are shown to proceed by a regioselective electrophilic aromatic substitution mechanism involving a stabilized Wheland intermediate.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1521-3765
DOI:	10.1002/chem.201600159