Tetrabromothiophene from 2-Bromothiophene by means of Sodium Acetylide in Liquid Ammonia

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.

Access options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

References

  1. 1

    Keskin, H., Miller, R. E., and Nord, F. F., J. Org. Chem., 16, 199 (1951).

  2. 2

    (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).

  3. 3

    Krause and Rennwanz, Ber., 62, 1710 (1934).

  4. 4

    Volhard and Erdmann, Ber., 18, 454 (1890).

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

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

Download citation

Further reading

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.