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Oxidation reactions of 4H-chalcogenopyrans

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have studied the oxidation of 4H-chalcogenopyrans and chalcogenopyrylium salts by lead tetraacetate. We have established that the major reaction products on oxidation of 2,6-diphenyl-4H-thiopyran and selenopyran are 2,6-diphenyl-4H-thio(seleno)pyran-4-ones, while 2-benzoyl-5-phenyl(seleno)thiophenes are formed as impurities. The major product on oxidation of 2,6-diphenyl-4H-pyran is 2-benzoyl-5-phenylfuran. We have shown that 2,4,6-triphenyl-4H-pyran does not undergo oxidation by hydrogen peroxide in neutral medium, in contrast to its S and Se analogs. This supports the hypothesis that the heteroatom participates in the oxidation process.

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References

  1. A. M. Plotnikov, A. D. Shebaldova, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 11, 1489 (1985).

  2. S. N. Petrakov, B. I. Drevko, L. A. Fomenko, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 7, 996 (1991).

  3. B. I. Drevko, M. I. Smushkin, L. A. Fomenko, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 1, 24 (1995).

  4. B. I. Drevko, L. A. Fomenko, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 6, 767 (1989).

  5. B. I. Drevko, M. I. Smushkin, and V. G. Kharchenko, Zh. Org. Khim., No. 9, 1437 (1995).

  6. B. I. Drevko, S. N. Petrakov, L. A. Fomenko, O. I. Zhukov, M. I. Shmushkin, E. V. Drevko, and V. G. Kharchenko, Zh. Org. Khim., No. 1, 115 (1994).

  7. V. G. Kharchenko and S. N. Chalaya, Thiopyrans, Thiopyrylium Salts, and Related Compounds [in Russian], Izdat. Saratovsk. Univ., Saratov (1987).

    Google Scholar 

  8. S. V. Krivun, G. N. Dorofeenko, and A. S. Koval'skii, Khim. Geterotsikl. Soedinen., No. 6, 737 (1970).

  9. V. G. Kharchenko and B. I. Drevko, USSR Inventor's Certificate 1,167,184; Byull. Izobret., No. 26 (1985).

  10. A. G. Blinokhvatov, O. V. Markovtseva, and M. N. Nikolaeva, Khim. Geterotsikl. Soedin., No. 3, 320 (1992).

  11. B. I. Drevko, L. M. Yudovich, and V. G. Kharchenko, USSR Inventor's Certificate 1,447,824; Byull. Izobret., No. 48 (1988).

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Authors
  1. B. I. Drevko
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  2. M. I. Smushkin
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  3. V. G. Kharchenko
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Additional information

N. G. Cherynshevskii Saratov State University, Saratov 410071. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 913–916, July, 1996. Original article submitted March 6, 1996.

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Drevko, B.I., Smushkin, M.I. & Kharchenko, V.G. Oxidation reactions of 4H-chalcogenopyrans. Chem Heterocycl Compd 32, 777–780 (1996). https://doi.org/10.1007/BF01165719

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  • DOI: https://doi.org/10.1007/BF01165719

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