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Influence of structure on the ratio and nature of the rotamers of vinyl ethers

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The separate assignment of the bands in the IR spectra of vinyl ethers to specific rotamers were systematized, and the influence of the structure on the population of conformations and the degree of p-π-conjugation in the vinyloxy group was studied on this basis.

  2. 2.

    The conjugation in the CH2=CHO system depends not only on the p-π-coplanarity (stericfactor), but also on the degree of displacement of the unshared electron pairs of the oxygen atom in the direction of the double bond, i.e., the inductive and resonance effects in the radical.

  3. 3.

    The fraction of the nonplanar (“unconjugated”) rotamer increases with increasing branching of the radical and with intensification of its negative inductive effect.

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR, USSR

    B. A. Trofimov, N. I. Shergina, A. S. Atavin, É. I. Kositsyna, A. V. Gusarov & G. M. Gavrilova

Authors
  1. B. A. Trofimov
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  2. N. I. Shergina
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  3. A. S. Atavin
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  4. É. I. Kositsyna
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  5. A. V. Gusarov
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  6. G. M. Gavrilova
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Translated from Izvestiya Akademii Nauk SSSR, No. 1, pp. 116–121, January, 1972.

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Trofimov, B.A., Shergina, N.I., Atavin, A.S. et al. Influence of structure on the ratio and nature of the rotamers of vinyl ethers. Russ Chem Bull 21, 103–108 (1972). https://doi.org/10.1007/BF00855665

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  • DOI: https://doi.org/10.1007/BF00855665

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