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DOI: 10.1055/s-2002-31958
A New, Improved and Convenient Synthesis of 4H-Cyclopenta[2,1-b:3,4-b′]-dithiophen-4-one
Publication History
Publication Date:
03 June 2002 (online)
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Abstract
A new and efficient three-step synthesis of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one (CDT) (1) is described. This was achieved by a one-pot, regiospecific synthesis of bis(2-iodo-3-thienyl)methanol (13), its subsequent oxidation to the bis(2-iodo-3-thienyl) ketone (14) which after Ullmann coupling yielded the title compound 1.
Key words
regiospecific lithiation - iodination - oxidation - Ullmann coupling - conducting polymers
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References
Mp 71.5-73.5 °C (from benzene-hexane, 1:4). 1H NMR (200 MHz, CDCl3): δ = 2.42 (br s, 1 H, OH), 5.88 (d, 1 H, J = 3.3, HOCH), 6.92 (d, 1 H, J = 5.6, 4-H), 7.03 (dd, 1 H, J = 4.9 and 1.4, 4′-H), 7.20-7.25 (m, 1 H, 2′-H), 7.28 (dd, 1 H, J = 4.9 and 3.1, 5′-H), 7.43 (d, 1 H, J = 5.9, 5-H). 13C NMR (50 MHz, CDCl3): δ = 70.6 (HOCH), 74.5 (2-C), 121.5, 126.0, 126.3, 126.6, 131.5, 143.7 (3- or 3′-C), 147.7 (3- or 3′-C). Anal. Calcd for C9H7IOS2: C, 33.55; H, 2.19; S, 19.91. Found: C, 33.64; H, 2.18; S, 19.70.