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Cycloaddition of norbornadiene to fluorine-containing heteroaddends

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Abstract

Cycloaddition reactions of norbornadiene with fluorinated heteroaddends (hexafluoro-acetone, dichlorotetrafluoroacetone, trifluoroacetonitrile, and N-trifluoroacetylhexafluoro-propan-2-imine) were studied. As a rule, the reactions follow the concerted mechanism. The reaction with bis(trifluoromethyl)ketene gave a mixture of tricyclene [2+2]- and [2+2+2]-cyclo-adducts formed along different pathways.

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References

  1. C. G. Krespan, B. C. McKusick, and T. L. Cairus, J. Am. Chem. Soc., 1961, 83, 3428.

    Article  Google Scholar 

  2. W. J. Middleton and E. M. Binham, J. Fluorine Chem., 1982, 20, 397.

    Article  Google Scholar 

  3. N. V. Vasil'ev, A. E. Patalakha, and A. V. Buzaev, Itogi Nauki Tekh., Ser.: Org. Khim., VINITI, Moscow, 1992, 23, 1.

    Google Scholar 

  4. US Pat. No. 2 928 865, 15.03.1960; Chem. Abstr., 1960, 54, 18393.

  5. A. E. Patalakha, N. V. Vasil'ev, and A. V. Buzaev, Khim. Fiz., 1994, 13, 65.

    Google Scholar 

  6. A. V. Fokin, A. F. Kolomiets, and N. V. Vasil'ev, Usp. Khim., 1984, 53, 398 [Russ. Chem. Rev., 1984, 53 (Engl. Transl.)].

    Google Scholar 

  7. A. J. Gordon and R. A. Ford, The Chemist's Companion. A Handbook of Practical Data, Techniques, and References, Wiley, New York—London—Sydney—Toronto, 1972.

    Google Scholar 

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 1013–1015, April, 2005.

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Vasil'ev, N.V., Truskanova, T.D., Buzaev, A.V. et al. Cycloaddition of norbornadiene to fluorine-containing heteroaddends. Russ Chem Bull 54, 1038–1040 (2005). https://doi.org/10.1007/s11172-005-0353-x

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  • DOI: https://doi.org/10.1007/s11172-005-0353-x

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