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Reaction of 3-aryl-2-benzoyloxiranes with alkyl thiocyanates

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Aryl-2-benzoyloxiranes and alkyl thiocyanates in the presence of an equivalent amount of anhydrous AlCl3 form erythro-N-(2-benzoyl-l-aryl-2-chloroethyl)-S-alkyl thiocarbamates and α-diketones. p-Toly1- and p-anisy1-2-benzoy1-oxiranes do not react with alkyl thiocyanates, but isomerize to the respective α-diketones, and form the threo-chlorohydrins in low yield.

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Literature cited

  1. I. G. Tishchenko, O. N. Bubel', and O. A. Grinkevich, Dokl. Akad. Nauk Bel. SSR,25 543 (1981).

    Google Scholar 

  2. I. G. Tishchenko, O. A. Grinkevich, O. N. Bubel', and A. V. Shavnya, Zh. Org. Khim.,20, 644 (1984).

    Google Scholar 

  3. A. B. Bothner-By, Adv. Magn. Reson.,1, 195 (1965).

    Google Scholar 

  4. A. Gordon and R. Ford, A Chemist's Companion, Wiley (1973).

  5. N. Ardabilchi, A. O. Fitton, J. R. Frost, E. K. Oppong-Boahie, A. H. Hadi, and A. Sharif, J. Chem. Soc., Perki Trans. 1, No. 2, 539 (1979).

  6. J. S. Dewar and W. Thiel, J. Am. Chem. Soc.,99, 4899 (1977).

    Google Scholar 

  7. E. Eliel, N. A1linger, S. Angyal, and G. Morrison, Conformational Analysis, Wiley (1965).

  8. O. N. Bubel', I. G. Tishchenko, G. Z. Stasevich, I. L. Romanko, A. F. Abramavov, and E. D. Skakovskii, Khim. Geterotsikl. Soedin., No. 7, 888 (1979).

  9. L. Reichel and A. Z. Neubauer, Z. Chem.,8, 423 (1968).

    Google Scholar 

  10. T. Uchida, J. Miyagi, and K. Harutama, Bull. Chem. Soc. Jpn.,48, 1071 (1975).

    Google Scholar 

  11. S. A. Korotkov, V. D. Orlov, I. S. Pivnenko, and V. F. Lavrushin, Ukr. Khim. Zh.,39, 1263 (1973).

    Google Scholar 

  12. G. H. Bennet and G. H. Willis, J. Chem. Soc., Part 2, 1960 (1928).

  13. T. J. Malkin, J. Chem. Soc., Part 1, 369 (1925).

    Google Scholar 

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Translated from Khimiya Geterotsilklicheskikh soedinenii, No. 12, pp. 1624–1628, December, 1985.

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Bubel', O.N., Tishchenko, I.G. & Grinkevich, O.A. Reaction of 3-aryl-2-benzoyloxiranes with alkyl thiocyanates. Chem Heterocycl Compd 21, 1335–1338 (1985). https://doi.org/10.1007/BF00842955

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  • DOI: https://doi.org/10.1007/BF00842955

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