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Reaction of sterically hindered o-benzoquinones with diazomethane

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

In contrast to certain o-benzoquinones, the sterically hindered o-quinones react with CH2N2 both at the oxygen atoms to give cyclic ethers, and at the C=C and C=O bonds of the quinoid ring; the predominant direction of the reaction depends on the ratio of the reactants.

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Literature cited

  1. B. Eistert, K. Pfleger, and P. Donath, Ber. Bunsenges Phys. Chem.,105, 3915 (1972).

    Google Scholar 

  2. C. J. P. Spruit, Rec. Trav. Chim.,74, 737 (1955).

    Google Scholar 

  3. G. Manecke and H. Hubner, Tetrahedron. Lett.,26, 2443 (1971).

    Google Scholar 

  4. B. Eistert and G. Bock, Ber. Bunsenges Phys. Chem.,92, 1247 (1959).

    Google Scholar 

  5. B. Eistert, H. Fink, K. Pfluger, and G. Kiiffner, Ann. Chem.,735, 145 (1970).

    Google Scholar 

  6. L. F. Fieser and J. L. Hartwell, J. Am. Chem. Soc.,57, 1479 (1935).

    Google Scholar 

  7. A. Schönberg, W. I. Awad, and N. Latiff, J. Chem. Soc.,1951, 1958.

  8. W. Rundel and P. Kästner, Ann. Chem.,731, 87 (1970).

    Google Scholar 

  9. F. Arndt, J. Amende, and W. Ender, Monatsh.,59, 210 (1932).

    Google Scholar 

  10. L. Homer and K. Sturm, Ann. Chem.,597, 1 (1955).

    Google Scholar 

  11. V. B. Vol'eva, V. V. Ershov, I. S. Belostotskaya, and N. L. Komissarova, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 739.

  12. I. S. Belostotskaya, V. B. Vol'eva, N. L. Komissarova, and V. V. Ershov, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 709.

  13. W. C. Howell, M. Ktenas, and J. M. MacDonald, Tetrahedron Lett.,26, 1719 (1964).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    N. L. Komissarova, I. S. Belostotskaya, V. B. Vol'eva, E. V. Dzhuaryan, I. A. Novikova & V. V. Ershov

Authors
  1. N. L. Komissarova
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  2. I. S. Belostotskaya
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  3. V. B. Vol'eva
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  4. E. V. Dzhuaryan
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  5. I. A. Novikova
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  6. V. V. Ershov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2360–2362, October, 1981.

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Komissarova, N.L., Belostotskaya, I.S., Vol'eva, V.B. et al. Reaction of sterically hindered o-benzoquinones with diazomethane. Russ Chem Bull 30, 1944–1946 (1981). https://doi.org/10.1007/BF00963430

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  • DOI: https://doi.org/10.1007/BF00963430

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