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Addition of dichlorocarbene to tricyclo[4.3.0.03,7]nona-4,8-diene

  • Organic Chemistry
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Abstract

Addition of dichlorocarbene to tricyclo[4.3.0.03,7]nona-4,8-diene (brexadiene) under conditions of phase transfer catalysis occurs from theexo side. Cyclopropyl-allyl rearrangement of intermediate chlorocyclopropanes yields tricyclo[5.4.0.03,8]undecadienes.

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References

  1. N. S. Zefirov, I. V. Kazimirchik, and K. A. Lukin,Tsikloprisoedinenie dikhlorkarbena k olefinan [Cycloaddition of Dichlorocarbene to Olefins], Nauka, Moscow, 1985, 151 pp (in Russian).

    Google Scholar 

  2. L. A. Yanovskaya and S. S. Yufit,Organicheskii sintez v dvukhfaznykh sistemakh [Organic Synthesis in Two-Phase Systems], Khimiya, Moscow, 1982, 184 p. (in Russian).

    Google Scholar 

  3. E. V. Lukovskaya, A. A. Bobylyova, T. I. Pehk, N. F. Dubitskaya, I. A. Petrushchenkova, and N. A. Belikova,Zh. Org. Khim., 1988,24, 1457,J. Org. Chem. USSR, 1988,24 (Engl. Transl.)].

    CAS  Google Scholar 

  4. W. R. Moore, W. R. Mozer, and J. E. La Prade,J. Org. Chem., 1963,28, 2200.

    CAS  Google Scholar 

  5. A. A. Bobylyova, A. V. Khoroshutin, E. V. Lukovskaya, T. Pehk, and N. A. Belikova,Mendeleev Commun., 1996, 112.

  6. A.A. Bobylyova, N. F. Dubitskaya, A. V. Khoroshutin, T. Pehk, and N. A. Belikova,Tetrahedron Lett., 1991, 6429.

  7. E. A. Masunov and P. M. ZorkiiZh. Fiz. Khim., 1992,66, 60, [Russ. J. Phys. Chem., 1992,66 (Engl. Transl.)].

    CAS  Google Scholar 

  8. D. Wege,J. Org. Chem., 1990,55, 1667.

    Article  CAS  Google Scholar 

  9. K. Kakiuchi, S. Kimanoya, S. Kobiro, Y. Tobe, and Y. Odaira,Bull. Chem. Soc. Jpn., 1990,63, 3358.

    Article  CAS  Google Scholar 

  10. T. L. Gilchrist and R. C. Storr,Organic Reactions and Orbital Symmetry, University Press, Cambridge, 1972.

    Google Scholar 

  11. M. Sato, T. Tanaka, J. Tsunetsugu, and S. Ebine,Bull. Chem. Soc. Jpn., 1975,48, 2395.

    Article  CAS  Google Scholar 

  12. E. V. Dehmlov and S. S. Dehmlov,Phase Transfer Catalysis, Verlag Chemie, Weinheim, 1983.

    Google Scholar 

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Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 8, pp. 1494–1497, August, 1997.

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Khoroshutin, A.V., Bobylyova, A.A., Pehk, T.I. et al. Addition of dichlorocarbene to tricyclo[4.3.0.03,7]nona-4,8-diene. Russ Chem Bull 46, 1430–1433 (1997). https://doi.org/10.1007/BF02505679

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  • DOI: https://doi.org/10.1007/BF02505679

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