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Structural orientation in the diene condensation of trans-piperylene with some nitro dienophiles

  • Organic and Biological Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    A study was made of structural orientation in the diene condensation of trans-piperylene with the nitro dienophiles RCH=CHNO2, in which R=H, CH3, C6H5, CCl3, COOCH3.

  2. 2.

    In the condensation of trans-piperylene with nitroethylene(R=H)the only reaction product is the ortho isomer.

  3. 3.

    In the condensation of trans-piperylene with 1,2-disubstituted nitro dienophiles (R=CH3, C6H5, CCl3, COOCH3) in all cases two structurally isomeric adducts are formed with a great predominance of the ortho isomer.

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Literature cited

  1. A. A Dudinskaya, G. A. Shvekhgeimer, and S. S. Novikov, Izv. AN SSSR. Otd. khim. n. 522 (1961).

  2. C. K. Ingold, Reaction Mechanism and the Structure of Organic Compounds [Russian translation], IL, Moscow (1959), p. 567.

    Google Scholar 

  3. E. Müller, Modern Views in Organic Chemistry [Russian translation], IL, Moscow (1960), p. 387.

    Google Scholar 

  4. W. C. Wildman, R. B. Wildman, W. T. Norton, and J. B. Tine, J. Amer. Chem. Soc.75, 1912 (1953).

    Google Scholar 

  5. H. Burkett and W. Wright, J, Organ. Chem.25, 276 (1960).

    Google Scholar 

  6. O. Wallach, Ann.359 303 (1908).

    Google Scholar 

  7. A. A. Dudinskaya, G. A. Shvekhgeimer, S. S Novikov, and V. I. Slovetskii, Izv. AN SSSR. Otd. khim. n. 182 (1961).

  8. K. Anwers and H. Wissebach, Ber.56, 728 (1923).

    Google Scholar 

  9. I. N. Nazarov, A. I. Kuznetsova, and N. V. Kuznetsov, Zh. obshch. khimii25, 88 (1955).

    Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences, USSR

    A. A. Dudinskaya, S. S. Novikov & G. A. Shvekhgeimer

Authors
  1. A. A. Dudinskaya
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  2. S. S. Novikov
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  3. G. A. Shvekhgeimer
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2024–2029, November 1965

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Dudinskaya, A.A., Novikov, S.S. & Shvekhgeimer, G.A. Structural orientation in the diene condensation of trans-piperylene with some nitro dienophiles. Russ Chem Bull 14, 1988–1992 (1965). https://doi.org/10.1007/BF00845896

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  • DOI: https://doi.org/10.1007/BF00845896

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