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The chemical behavior of 2-methylene-2,3-dihydro-3-furanones

14. 5-Aryl-2-methoxycarbonylmethylene-2,3-dihydro-3-furanones in the [2+2]-cycloaddition of diphenylketene

Abstract

Diphenylketene undergoes regioselective thermal [2+2]-cycloaddition to the heterocyclic C(3)=O carbonyl group of 5-aryl-2-methoxycarbonylmethylene-2,3-dihydrofuran-3-ones and 5-phenyl-2,3-dihydrofuran-2,3-dione to give the corresponding 3-diphenylmethylene derivatives of 2,3-dihydrofuran.

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References

  1. 1.

    Z. G. Aliev, E. N. Koz'minykh, N. M. Igidov, V. O. Koz'minykh, Yu. S. Andreichikov, and L. O. Atovmyan,Izv. Akad. Nauk, Ser. Khim., 1994, 306 [Russ. Chem. Bull., 1994,43, 286 (Engl. Transl.)].

  2. 2.

    Yu. S. Andreichikov and S. N. Shurov,Khim. Zh. Ural'skikh Universitetov [Chem. J. Ural Univ.], Perm', 1992,1, 49 (in Russian).

  3. 3.

    S. N. Shurov, E. Yu. Pavlova, L. I. Livantsova, G. S. Zaitseva, and Yu. S. Andreichikov,Zh. Org. Khim., 1993,29, 2275 [Russ. J. Org. Chem., 1993,29 (Engl. Transl.)].

  4. 4.

    E. Terpetschnig, G. Penn, G. Kollenz, K. Peters, E.-M. Peters, and H. G. Schnering,Tetrahedron, 1991,47, 3045.

  5. 5.

    T. N. Yanborisov, S. N. Shurov, Yu. S. Andreichikov, and V. G. Baklykov,Zh. Org. Khim., 1990,26, 1369 [J. Org. Chem. USSR, 1990,26 (Engl. Transl.)].

  6. 6.

    J. S. Hastings and H. G. Heller,J. Chem. Soc. Perkin Trans, 1, 1972, 1839.

  7. 7.

    J. S. Hastings, H. G. Heller, and K. Salisbury,J. Chem. Soc. Perkin Trans, 1, 1975, 1995.

  8. 8.

    Yu. S. Andreichikov, V. O. Koz'minykh, and E. N. Manelova,Zh. Org. Khim., 1985,21 [J. Org. Chem. USSR, 1985,21 (Engl. Transl.)].

  9. 9.

    V. O. Koz'minykh, E. N. Koz'minykh, and Yu. S. Andreichikov,Khim. Geterotsikl. Soedin., 1989, 1034 [Chem.Heterocycl. Compd., 1989 (Engl. Transl.)].

  10. 10.

    V. O. Kozminykh, N. M. Igidov, E. N. Kozminykh, and Z. G. Aliev,Pharmazie, 1993,48, 99.

  11. 11.

    Weygand-Hilgetag,Organisch-chemische Experimentierkunst, Verlag Leipzig, 1964.

  12. 12.

    V. O. Koz'minykh, N. M. Igidov, and Z. N. Semenova,Poisk biologicheski aktivnykh veshchestv i problemy lekarstvennogo obespecheniya [Search for Biologically Active Substances and Problems of Drug Provision], Ufa, 1991, 21 (in Russian).

  13. 13.

    E. N. Koz'minykh, N. M. Igidov, G. A. Shavkunova, and V. O. Koz'minykh,Farmatsiya i farmakologiya [Pharmtacy and Pharmacology], Perm', 1993, 89 (in Russian).

  14. 14.

    L. Bellamy,Novye dannye po IK-spektram slozhnykh molekul [New Data on IR spectra of organic compounds], Mir, Moscow, 1971, 176 (Russ. Transl.).

  15. 15.

    Yu. S. Andreichikov and V. O. Koz'minykh, USSR Author's Certficate 1077891 (1982);Byull. Izobret., 1984, N 9, 60 (in Russian).

  16. 16.

    O. Isler, H. Gutmann, M. Montavon, R. R'egg, G. Ryser, and P. Zeller,Helv. Chim. Acta, 1957,40, 1242.

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 331–334, February, 1995.

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Igidov, N.M., Kozminykh, E.N., Shavkunova, G.A. et al. The chemical behavior of 2-methylene-2,3-dihydro-3-furanones. Russ Chem Bull 44, 322–325 (1995). https://doi.org/10.1007/BF00702145

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Key words

  • 5-aryl-2-methoxycarbonylmethylene-2,3-dihydrofuran-3-ones
  • 5-phenyl-2,3-dihydrofuran-2,3-dione
  • diphenylketene
  • [2+2]-cycloaddition reaction
  • 5-aryl-3-diphenylmethylene-2,3-dihydrofurans