Abstract
IN the course of our investigations on acetylenic compounds in the thiophene series1, it was desired to synthesize 2-thienylacetylene directly from 2-bromothiophene and 2-chlorothiophene by means of sodium acetylide in liquid ammonia. Although it is known that arylations via this method are unsuccessful when applied to halides in the benzene series2a,b, no experiments are recorded in the literature with heterocyclic compounds. In view of the greater reactivity of the thiophene nucleus, it appeared worth while to attempt this reaction.
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References
Keskin, H., Miller, R. E., and Nord, F. F., J. Org. Chem., 16, 199 (1951).
(a) Vaughn, T. H., Hennion, G. H., Vogt, R. R., and Nieuwland, J. A., J. Org. Chem., 2, 1 (1937). (b) Jacobs, Thomas J., “Organic Reactions”, 5 (John Wiley and Sons, Inc., New York, 1949).
Krause and Rennwanz, Ber., 62, 1710 (1934).
Volhard and Erdmann, Ber., 18, 454 (1890).
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VAITIEKUNAS, A., NORD, F. Tetrabromothiophene from 2-Bromothiophene by means of Sodium Acetylide in Liquid Ammonia. Nature 168, 875–876 (1951). https://doi.org/10.1038/168875a0
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DOI: https://doi.org/10.1038/168875a0
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