title: Unprecedented Demonstration of Regioselective SE Ar Reaction giving Unsymmetrical Regioregular Oligothiophenes.
abstract: 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.
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France.
authors.forename: Chady
authors.initials: C
authors.lastname: Moussallem
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France.
authors.forename: Simon
authors.initials: S
authors.lastname: Olivier
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France.
authors.forename: Jérémie
authors.initials: J
authors.lastname: Grolleau
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France.
authors.forename: Magali
authors.initials: M
authors.lastname: Allain
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Mallet
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France.
authors.forename: Gurunathan
authors.initials: G
authors.lastname: Savitha
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France. Frederic.gohier@univ-angers.fr.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Gohier
authors.affiliation: MOLTECH-Anjou, UMR CNRS 6200, University of Angers, 2 Bd. Lavoisier, 49045, Angers, France. pierre.frere@univ-angers.fr.
authors.forename: Pierre
authors.identifier: http://orcid.org/0000-0002-4512-9444
authors.initials: P
authors.lastname: Frère
mesh_terms: D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*
chemical_list: C000611366:4-cyano-3-oxotetrahydrothiophene; C000611367:4-cyano-3-pyrrolidylthiophene; D011759:Pyrrolidines; D013876:Thiophenes
keywords: electrophilic substitution; oligomerization; organic synthesis; regioselectivity; thiophenes