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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 2
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Original Articles

Synthesis and Reactivity of the 2,5-Bis(Trimethylstannyl) Derivatives of Thiophene and Furan

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Pages 121-128 | Published online: 05 Dec 2006

References

  • (a) Department of Chemistry, (b) Department of Medicinal Chemistry and Pharmacology, (c) Joint Program in Nuclear Medicine.
  • Seitz , D. E. , Tonnesen , G. L. , Hellman , S. , Hanson , R. N. and Adelstein , S. J. 1980 . J. Organomet. Chem. , 186 : C33 Seitz, D. E., Milius, R. A., and El-Wakil, H., Synthetic Commun., 11, 281 (1981); Tonnesen, G. L., Hanson, R. N., Seitz, D. E., and Bottaro, J. C., Int. J. Nucl. Med. Biol., in press.
  • All new compounds exhibited spectral data in full accord with assigned structures and gave satisfactory combustion analyses
  • Chadwick , D. J. and Willbe , C. 1977 . J. Chem. Soc., Perkin Trans. 1 , : 887 For a discussion of the 2,5-dilithiation of thiophene and furan, see:
  • Seitz , D. E. and Zapata , A. 1980 . Tetrahedron Lett. , : 3451 Seitz, D. E. and Zapata, A., Synthesis, 557 (1981); Seitz, D. E. and Zapata, A., Synthetic Commun., 11, 673 (1981)
  • Gronowitz , S. and Gestblom , B. 1962 . Arkiv Kemi (English Translation) , 18 : 513
  • Gilman , H. and Wright , G. F. 1933 . J. Am. Chem. Soc. , 55 : 3302
  • For comparison purposes, a sample of 2,5-diiodothiophene was secured in 96% yield from 1 by reaction with iodine in tetrahydrofuran.

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