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Present address: Acreo AB, Bredgatan 34, SE-602 21 Norrköping, Sweden.
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Present address: Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park, SE-141 57 Huddinge, Sweden.
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Present address: AstraZeneca R&D, SE-151 85 S̈dertälje, Sweden..
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7. For instance, TOT3T 29 is a terthiophene, which is end-capped with thioxano rings.
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0142084258
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A literature search with Beilstein Commander and Scifinder Scholar in May 2003 found 20 substances containing 5 as a substructure, other than those reported by us in preliminary communications. Only 3 of these contain a peripheral ethylenedithio bridge. No compound with the substructure 6 was found, and only 3 compounds based on 7.
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3-Methoxythiophene (10) is commercially available, but it can also be readily synthesized from 3-bromothiophene: Keegstra, M. A.; Peters, T. H. A.; Brandsma, L. Synth. Commun. 1990, 20, 213.
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The NMR shifts of the thiophene protons of the main product are more consistent with the structure 13 than with 12. The aromatic part of the spectrum resembles the spectrum for 16, which is similar to 13, but the shift for the 2-proton is considerable higher than for the 2-proton in 3-methoxythiophene 10 and other 3-alkoxythiophenes. For spectral data for a derivative of 12, see:Chaffin, J. D. E.; Barker, J. M.; Huddleston, P. R. J. Chem. Soc., Perkin. Trans. 1 2001, 1398.
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During the preparation of this manuscript, a similar synthesis of 27 was reported:Melucci, M.; Barbarella, G.; Sotgiu, G. J. Org. Chem. 2002, 67, 8877.
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