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Synthesis and some properties of free radicals with triple bonds

Conclusions

  1. 1.

    Free radicals containing triple bonds in the substituents, tris-(p-tolanyl)methyl (I) and diphenyl-(p-phenylethynyl) phenylmethyl (II), were produced.

  2. 2.

    The EPR spectra of the radicals (I) and (II) were taken and analyzed. A weak hyperfine (0.1 Gs) interaction of the unpaired electron with the protons of the far phenyl rings was detected.

  3. 3.

    Approximately 10% of the spin density of the unpaired electron is transmitted from the triphenylmethyl rings through the triple bond.

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Literature cited

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    I. L. Kotlyarevskii and N. I. Popova, Izv. Akad. Nauk SSSR, Ser. Khim.,208 (1967).

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    O. Fisher and W. Hess, Ber.,38, 336 (1905).

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    H. O. Wirth and O. Königstein, Liebigs Ann. Chem.,634, 84 (1960).

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    D. B. Chesnut and G. J. Sloan, J. Chem. Phys.,33, 637 (1960).

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    R. D. Stephens and C. E. Castro, J. Organ. Chem.,28, 3313 (1963).

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    E. F. Pratt and S. P. Suskind, J. Organ. Chem.,28, 638 (1963).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2424–2430, November, 1969.

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Popova, N.I., Skubnevskaya, G.I., Molin, Y.N. et al. Synthesis and some properties of free radicals with triple bonds. Russ Chem Bull 18, 2271–2275 (1969). https://doi.org/10.1007/BF00906493

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Keywords

  • Methyl
  • Free Radical
  • Phenyl
  • Phenyl Ring
  • Spin Density