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Communication | Regular issue | Vol 20, No. 10, 1983, pp.1937-1940
Published online, 1st January, 1970
DOI: 10.3987/R-1983-10-1937
The Synthesis od Alpha-thiophene Oligomers by Oxidative Coupling of 2-Lithiothiophenes

Jacques Kagan and Sudershan K. Arora

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.


Alpha-thiophene oligomers containing an even number of thiophene rings can be obtained with very good yields by reacting a suitable thiophene precursor with 0.5 equivalent of lithium diisopropylamide in dry THF, followed by the oxidation of the α-lithio derivative with cupric chloride. The Scheme is illustrated with the synthesis of 2,2’-bithienyl, α-quaterthienyl, and α-sexithienyl in 83, 85, and 73% yields from thiophene, 2,2’-bithienyl, and α-terthienyl respectively.