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Synthetic Access to Hydrogen and Halogen Derivatives of 3‐Amino‐4‐nitrothiophenes
Author(s) -
Vogt EvaJanina,
Zapol'skii Viktor A.,
Nutz Eva,
Kaufmann Dieter E.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300006
Subject(s) - chemistry , halogen , halogenation , monomer , nucleophile , combinatorial chemistry , unit (ring theory) , chemoselectivity , hydrogen , push pull , organic chemistry , polymer , catalysis , alkyl , mathematics education , mathematics , electrical engineering , engineering
The unique synthesis of 3‐amino‐4‐nitrothiophenes 2 provides easy access to reference species of a new family of push‐pull substituted thiophenes. The chemoselective modification of 2 into suitable derivatives was accomplished by selective S ‐oxidation of the vinylsulfanyl unit, followed by substitution of the vinylsulfinyl group of 3 by nucleophiles. Dihalothiophenes were formed this way in very good yields. A subsequent selective dehalogenation at the 2, 5 or 2 and 5 positions also proved feasible, and the push‐pull unit was untouched. The new 2,5‐dihalothiophenes could be interesting monomers for conducting polymers.