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Mediated electrochemical reduction of dibromonorcarane in an emulsified system using Cr(II)

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Abstract

High material yields were obtained in the indirect electrochemical reduction of 7,7-dibromobicyclo-[4-1-0]heptane (dibromonorcarane) to give the corresponding monobromo derivative in an ethylene chloride/water emulsion. The reducing agent was Cr(II) generated by current controlled electrolysis of aqueous chromic chloride at a silver cathode. The effect of the concentration of Cr(II) and the temperature was studied. At 0.1 M Cr(II) and at 40° C the best results were obtained (90% yield).

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References

  1. C. L. Osborn, T. C. Shields, B. A. Shoulders, C. G. Cardenas and P. D. Gardner,Chem. Ind. (London) (1965) 766.

  2. D. Seyferth and B. Prokai,J. Org. Chem. 31 (1966) 1702.

    Google Scholar 

  3. M. Schlosser and G. Heinz,Angew. Chem. 79 (1967) 617.

    Google Scholar 

  4. H. Yamanaka, R. Oshima and K. Teramura,J. Org. Chem. 37 (1972) 1734.

    Google Scholar 

  5. D. Seyferth, H. Yamazoki and D. L. Alleston,J. Org. Chem. 28 (1963) 703.

    Google Scholar 

  6. L. Sydnes and L. Skahebol,Tetrahedron Lett. 42 (1974) 3707.

    Google Scholar 

  7. G. Guillaumet, L. Mordenti and P. Caubere,J. Organomet. Chem. 102 (1975) 353.

    Google Scholar 

  8. A. J. Fry and R. H. Moore,J. Org. Chem. 33 (1968) 1283.

    Google Scholar 

  9. R. E. Erickson, R. Annino, M. D. Scanlon and G. Zon,J. Am. Chem. Soc. 91 (1969) 1767.

    Google Scholar 

  10. H. Fees and H. Wendt, ‘Performance of two-phase-electrolyte electrolysis’ in Techniques of Electroorganic Synthesis, Part III (edited by N. Weinberg), J. Wiley, New York (1982).

    Google Scholar 

  11. H. Fees and H. Wendt,Ber. Bunsenges. Phys. Chem. 85 (1981) 914.

    Google Scholar 

  12. M. C. Giordano and L. Sereno, ‘Electrocatálisis y produción electroquímica de sustancias’, Monografia Acad. Nac. Cs. Ex. Fis. Nat. Buenos Aires, vol. 2 (1982).

  13. K. Kramer and P. Robertson,J. Appl. Electrochem. 10 (1980) 29.

    Google Scholar 

  14. M. Venkatalachapathy, R. Ramashwamy and H. Udupa,Bull. Acad. Sci. Chem. 6 (1958) 487.

    Google Scholar 

  15. R. Tomat and E. Vecchi,J. Appl. Electrochem. 1 (1971), 185.

    Google Scholar 

  16. D. Pletcher and G. Smilgin,J. Appl. Electrochem. 11 (1981) 601.

    Google Scholar 

  17. D. Pletcher and N. Tomov,J. Appl. Electrochem. 7 (1977) 501.

    Google Scholar 

  18. D. Pletcher and N. Tait,J. C. S. Perkin II (1979) 788.

    Google Scholar 

  19. Z. Ibrisagic, D. Pletcher, W. N. Brooks and K. P. Healy,J. Appl. Electrochem. 15 (1985) 719.

    Google Scholar 

  20. F. Lapicque and A. Storck,Electrochim. Acta 30 (1985) 1247.

    Google Scholar 

  21. J. Wellman and E. Steckhan,Synthesis (1978) 901.

  22. H. Nozaki, T. Aratani and R. Noyori,Tetrahedron 23 (1967) 3645.

    Google Scholar 

  23. L. M. Yudi, A. M. Baruzzi and V. M. Solís,J. Appl. Electrochem. 18 (1988) 417.

    Google Scholar 

  24. C. D. Wu, D. A. Scherson, E. J. Calvo, E. B. Yeager and M. A. Reid,J. Electrochem. Soc. 133 (1986) 2109.

    Google Scholar 

  25. A. Skathebol,Tetrahedron Lett. 16 (1973) 1367.

    Google Scholar 

  26. Ch. A. Mackenzie, in ‘Experimental organic chemistry’, (3rd edn.), Prentice-Hall, Inc. (1967) p. 77.

  27. H. Taube and H. Myers,J. Am. Chem. Soc. 76 (1954) 2103.

    Google Scholar 

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Yudi, L.M., Baruzzi, A.M. & Solis, V.M. Mediated electrochemical reduction of dibromonorcarane in an emulsified system using Cr(II). J Appl Electrochem 18, 687–690 (1988). https://doi.org/10.1007/BF01016893

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  • DOI: https://doi.org/10.1007/BF01016893

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