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Stereochemistry of cyclic compounds. Communication 61. Structural and steric orientation in the diene condensations of some vinylcycloalkenes with unsymmetrical trans dienophiles

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Summary

  1. 1.

    The diene condensation of 1-(1-chlorovinyl)cyclohexene (IV) with trans-3-(chloroformyl)acrylic esters and with methyl trans-3-nitroacrylate goes structurally and sterically selectively with formation of trans-syn adducts with the more electronegative group in the ortho position.

  2. 2.

    The condensation of methyl trans-3-nitroacrylate with 1-vinylcyclohexene (I) was studied, and the structure and configurations of the isomeric adducts formed were proved.

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Literature cited

  1. 1.

    G. M. Segal', L. P. Rybkina, and V. F. Kucherov, Izv. AN SSSR. Ser. khim.,1963, 1253.

  2. 2.

    G. M. Segal', L. P. Rybkina, and V. F. Kucherov, Izv. AN SSSR. Ser. khim.,1963, 1421.

  3. 3.

    U. Eisner, F. A. Elvidge, and R. P. Linstead, J. Chem. Soc.,1951, 1501.

  4. 4.

    I. N. Nazarov, V. F. Kucherov, and V. M. Andreev, Izv. AN SSSR. Otd. khim. n.,1956, 1091.

  5. 5.

    H. Schechter, F. Conrad, and A. Daulton, J. Amer. Chem. Soc.,74, 3052 (1952).

  6. 6.

    N. Kornblum and L. Fishbein, J. Amer. Chem. Soc.,77, 6266 (1955); J. Weinstock and N. Schwart, J. Organ. Chem.,26, 5247 (1961).

  7. 7.

    H. Ruschig, W. Fritsch, J. Smidt-Thome, and W. Haede, Chem. Ber.88, 883 (1955).

  8. 8.

    W. Hückel, Ber.,57B, 1285 (1924); Ann.,441, 1 (1925).

  9. 9.

    I. N. Nazarov, V. F. Kucherov, and V. M. Andreev, Izv. AN SSSR. Otd. khim. n.,1957, 331.

  10. 10.

    J. W. Cook and C. A. Lawrence, J. Chem. Soc.,1937, 817.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8 pp. 1463–1470, August, 1964

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Segal', G.M., Rybkina, L.P. & Kucherov, V.F. Stereochemistry of cyclic compounds. Communication 61. Structural and steric orientation in the diene condensations of some vinylcycloalkenes with unsymmetrical trans dienophiles. Russ Chem Bull 13, 1368–1373 (1964). https://doi.org/10.1007/BF00850336

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Keywords

  • Methyl
  • Ester
  • Adduct
  • Cyclohexene
  • Diene