DOI QR코드

DOI QR Code

The Reactivity of Thiopyrylium Compound. Reduction of Thiopyrylium Cation by Alkali Metals-Evidence of Thiabenzene Radical

  • Published : 1980.09.30

Abstract

For the first time we have synthesized thiabenzene radical by the reaction of thiopyrylium cation with alkali metals. As might be expected for a free radical, ESR-spectrum of 2,4,6-triphenylthiabenzene radical shows the single signal with g-value of 2.0045. The proton signal of 2,4,6-triphenylthiabenzene radical in nmr spectrum shifts to the higher field than that of 2,4,6-triphenylthiopyrylium cation by ca. 0.5 ppm. From the UV-spectrum of thiabenzene radical the presence of 6${\pi}$ non-benzenoid aromatic system was observed as in the case of thiopyrylium cation. The reactivity of alkali metals with thiopyrylium cation increases in the order of decreasing ionization energy, Li

Keywords

References

  1. Helv. Chim. Acta. v.39 R. Wizinger;S. Losinger;P. Ultrich
  2. Helv. Chim. Acta v.39 R. Wizinger;P. Ultrich
  3. Tetrahedron v.29 S. Yoneda;T. Sugamoto;Z. Yoshida
  4. J. Org. Chem. v.38 Z. Yoshida;H. Sugamoto;T. Sugamoto;S. Yoneda
  5. J. Amer. Chem. Soc. v.96 A. G. Hortmann;R. L. Harris
  6. Chemistry Letters, Japan Z. Yoshida;S. Yoneda;T. Sugimoto
  7. Tetrahedron v.28 Z. Yoshida;H. Sugamoto;S. Yoneda
  8. J. Amer. Chem. Soc. v.97 B. E. Maryanoff;J. Stockhous;K. Mislow
  9. J. Amer. Chem. Soc. v.91 M. P. M. Siskin;C. C. Price
  10. J. Amer. Chem. Soc. v.96 K. Mislow;B. E. Maryanoff;G. H. Senkler;J. Stockhous
  11. J. Org. Chem. v.36 C. C. Price;J. Follweiler;H. Pirelahi;M. Siskin