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Steric structure of phosphorus-containing heterocycles

Communication 4. Axial arrangement of the alkoxy group in 1,3, 2-dioxaphosphorinanes according to the data of the method of dipole moments

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

Conclusions

  1. 1.

    The dipole moment of 2-alkoxy- and 2-phenoxy-l, 3,2-dioxaphosphorinanes and their spiro analogs with a tricoordinated phosphorus atom were determined.

  2. 2.

    A graphical method was proposed for the analysis of the data of the method of dipole moments of cyclic compounds.

  3. 3.

    In all the compounds studied, a chair conformation with axial (or diaxial for the spiro compound) arrangement of the alkoxy group with a gauche-orientation of the methoxyl and ethoxyl radicals and a cisorientation of the phenoxy group is realized.

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Literature cited

  1. B. A. Arbuzov, R. P. Arshinova, A, N. Vereshchagin, and S. G. Vul'fson, Izv. Akad. Nauk SSSR, Ser. Khim., 1964 (1973).

  2. B. A. Arbuzov, R. P. Arshinova, A. N. Vereshchagin, S. G. Vul'fson, O. N. Nuretdinova, and L. Z. Nikonova, Khimiya Geterotsikl. Soed., 1324 (1971).

  3. D. W. White, R. D. Bertrand, G. K. McEwen, and J. G. Verkade, J. Amer. Chem. Soc.,92, 7125 (1970).

    Google Scholar 

  4. W. G. Bentrude and I. H. Hargis, J. Amer. Chem. Soc.,92, 7136 (1970).

    Google Scholar 

  5. C. L. Bodkin and P. Simpson, J. Chem. Soc., B, 1136 (1971).

    Google Scholar 

  6. M. Haemers, R. Ottinger, T. Reisse, and D. Zimmermann, Tetrahedron Letters, 461 (1971).

  7. D. W. White, G. K. McEwen, and J. G. Verkade, Tetrahedron Letters, 5369 (1968).

  8. B. A. Arbuzov, R. P. Arshinova, Yu. M. Mareev, and V. S. Vinogradova, Dokl. Akad. Nauk SSSR,208, 849 (1973).

    Google Scholar 

  9. M. J. Aroney, L. H. Chia, R. J. W. Le Fevre, and J. D. Saxby, J. Chem. Soc., 2948 (1964).

  10. O. Exner and V. Jehlicka, Collect, Czechoslov. Chem. Comm.,30, 639 (1965).

    Google Scholar 

  11. H. J. Lucas, F. W. Mitchell, and C. N. Scully, J. Amer. Chem. Soc.,72, 5491 (1950).

    Google Scholar 

  12. D. C. Ayres and H. M. Rydon, J. Chem. Soc., 1109 (1957).

  13. J. Hechenbleikner, and F. C. Lanoue, US Patent No. 2.847.443, 1958; Abstrs.52, 9251 (1958).

    Google Scholar 

  14. L. Friedman and H. Gould, US Patent No. 3,053,878, 1962; Chem. Abstrs.,58, 3354b (1963).

    Google Scholar 

  15. A. N. Vereshchagin and L. A. Grozina, Teoret. i Éksperim. Khimiya,4, 361 (1968).

    Google Scholar 

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Additional information

For Communication 3, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2426–2431, November, 1973.

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Arbuzov, B.A., Arshinova, R.P., Vul'fson, S.G. et al. Steric structure of phosphorus-containing heterocycles. Russ Chem Bull 22, 2372–2376 (1973). https://doi.org/10.1007/BF00926374

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  • DOI: https://doi.org/10.1007/BF00926374

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