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Reaction of 2,6-dibenzylidenecyclohexanone with phosphorus pentachloride: Triple functionalization of the isosemiquinoid system

  • Organic Chemistry
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Abstract

The reaction of 2,6-dibenzylidenecyclohexanone with PCl5 occursvia the sequential stages of desoxychlorination and substitutional phosphorylation to form (after oxidation, methoxylation, and hydrolysis on the surface of the chromatographic SiO2 adsorbent) organophosphorus products of the 1-(a-chloro-, a-hydroxy-, or α-alkoxy)benzyl-2-chloro-3-(α-(dimethylphosphoryl)benzylidene)cyclobex-1-ene series.

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References

  1. V. A. Nikanorov, V. I. Rozenberg, A. D. Rogachev, M. V. Galakhov, V. V. Kaverin, V. P. Yur'ev, and O. A. Reutov,Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 2865 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987,36, 2662 (Engl. Transl.)].

    Google Scholar 

  2. B. A. Arbuzov, V. M. Zoroastrova, G. A. Tudrii, and A. V. Fuzhenkova,Izv. Akad. Nauk SSSR, Ser. Khim., 1972, 2545 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1972,21, 2473 (Engl. Transl.)].

    Google Scholar 

  3. M. S. Newman and L. L. Wood, Jr.,J. Am. Chem. Soc., 1959,81, 4300, 6450.

    Google Scholar 

  4. J. R. Merchant and V. B. Desai,J. Chem. Soc., 1968, 499.

  5. S. V. Fridland and Yu. K. Malkov, inReaktsii i metody issledovaniya organicheskikh soedinenii [Reactions and Methods for Investigation of Organic Compounds], Khimiya, Moscow, 1986, 106 (in Russian).

    Google Scholar 

  6. A. V. Fokin, A. F. Kolomiets, and V. S. Shchennikov,Zh. Obshch. Khim., 1972,42, 801 [J. Gen. Chem. USSR, 1972,42 (Engl. Transl.)].

    Google Scholar 

  7. V. E. Kolbina, V. G. Rozinov, V. I. Glukhikh, and G. V. Ratovskii,Zh. Obshch. Khim., 1978,48, 2795 [J. Gen. Chem. USSR, 1978,48 (Engl. Transl.)].

    Google Scholar 

  8. P. Laszlo,Acc. Chem. Res., 1986,19, 121.

    Google Scholar 

  9. V. V. Veselovsky, A. S. Gybin, A. V. Losanova, A. M. Moiseenkov, W. A. Smit, and R. Caple,Tetrahedron Lett., 1988,29, 175.

    Google Scholar 

  10. J. B. Bentlez, K. B. Everard, and R. J. B. Marden,J. Chem. Soc., 1949, 2959.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 441–443, February, 1996.

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Nikanorov, V.A., Rogachev, A.D., Galakhov, M.V. et al. Reaction of 2,6-dibenzylidenecyclohexanone with phosphorus pentachloride: Triple functionalization of the isosemiquinoid system. Russ Chem Bull 45, 424–426 (1996). https://doi.org/10.1007/BF01433987

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  • DOI: https://doi.org/10.1007/BF01433987

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