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Decyclization of chiorocyclohexanone hydroperoxides under the action of ferrous salts

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

The decomposition of 2-chloro-, 2,2-dichloro-, and 2,6-dichloro-substituted cyclohexanone hydroperoxides on treatment with ferrous chloride and sulfate to give chloro-substituted aliphatic acids was investigated. A method for the synthesis of 2,6,6-trichlorohexanoic and 2,6,7,11-tetrachlorododecane-1,12-dioic acids was elaborated.

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References

  1. M. S. Kharash and G. Sosnovsky,J. Org. Chem., 1958,23, 1322.

    Google Scholar 

  2. A. Citterio and E. Vismara,Synthesis, 1980, 751.

  3. G. I. Nikishin, A. V. Aleksandrov, A. V. Ignatenko, and E. K. Starostin,Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 2628 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1984,33, 2407 (Engl. Transl.)].

    Google Scholar 

  4. F. Minisci and V. Pallini,Gazz. Chim. Ital., 1959,89, 2438.

    Google Scholar 

  5. H. E. De La Mare, J. K. Kochi, and F. F. Rust,J. Am. Chem. Soc., 1963,85, 1437.

    Google Scholar 

  6. V. L. Antonovskii, inOrganicheskie perekisnye initsiatory [Organic Peroxide Initiators], Khimiya, Moscow, 1972, 135 (in Russian).

    Google Scholar 

  7. D. C. Nonhebel and J. C. Walton,Free-Radical Chemistry, Cambridge University Press, Cambridge, 1974.

    Google Scholar 

  8. R. Kh. Freidlina, A. B. Terent'ev, M. Ya. Khorlina, and S. Ya. Aminov,Zh. Vses. Khim. Obshch. im D. I. Mendeleeva [J. of D. I. Mendeleev All-Union Chem. Soc.], 1966,11, 211 (in Russian).

    Google Scholar 

  9. Organic Syntheses, J. Wiley-Chapman and Hall, New York-London, 1949.

  10. Org. Synth. Col., J. Wiley, New York, 1963,3, 188.

  11. E. I. Corey and H. J. Burke,J. Am. Chem. Soc., 1955,77, 5148.

    Google Scholar 

  12. K. Weygand and G. Hilgetag,Organisch-Chemische Experimentierkunst, J. A. Barth Verlag, Leipzig, 1964.

    Google Scholar 

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 143–146, January, 1996.

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Starostin, E.K., Gushchin, V.V., Ignatenko, A.V. et al. Decyclization of chiorocyclohexanone hydroperoxides under the action of ferrous salts. Russ Chem Bull 45, 133–136 (1996). https://doi.org/10.1007/BF01433747

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  • DOI: https://doi.org/10.1007/BF01433747

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