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Stereochemistry of seven-membered heterocycles. Communication 14. Synthesis and three-dimensional structure of 4-methyl-1,3-dioxa-5,6-benzocycloheptenes

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    On the basis of data obtained by the dipole moment method, cis-2-methyl (or phenyl)-4-methyl-1,3-dioxa-5,6-benzocycloheptenes have an equilibrium of chair and twist forms that is close in quantitative respects to the related 2-R-phthalyacetals; the spiroketal of cyclohexanone is realized in the e-Tw form; the methylal is conformationally inhomogeneous.

  2. 2.

    The isomeric 2-tert-butyl-4-methyl-1,3-dioxa-5,6-benzocycloheptenes, according to13C NMR data, are realized in chair conformations. An analysis has been made of the influence of the 4-methyl group on the chemical shifts of the carbon atoms of the seven-membered ring.

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Authors and Affiliations

  1. A. M. Butlerov Chemical Institute, USSR

    E. N. Klimovitskii, G. N. Sergeeva, D. Yu. Strel'nik & B. A. Arbuzov

  2. V. I. Ul'yanov-Lenin Kazan' State University, USSR

    E. N. Klimovitskii, G. N. Sergeeva, D. Yu. Strel'nik & B. A. Arbuzov

Authors
  1. E. N. Klimovitskii
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  2. G. N. Sergeeva
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  3. D. Yu. Strel'nik
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  4. B. A. Arbuzov
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Additional information

For Communication 13, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2259–2265, October, 1984.

The authors wish to express their appreciation to P. P. Chernov for taking the13C NMR spectra.

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Klimovitskii, E.N., Sergeeva, G.N., Strel'nik, D.Y. et al. Stereochemistry of seven-membered heterocycles. Communication 14. Synthesis and three-dimensional structure of 4-methyl-1,3-dioxa-5,6-benzocycloheptenes. Russ Chem Bull 33, 2060–2065 (1984). https://doi.org/10.1007/BF00954082

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