Reaction of benzylidenephenylsulfonylacetophenone with trimethyl phosphite and tris(dimethylamino) phosphine

  • B. A. Arbuzov
  • Yu. V. Belkin
  • N. A. Polezhaeva
Organic and Biological Chemistry
  • 20 Downloads

Conclusions

  1. 1.

    Benzylidenephenylsulfonylacetophenone (I) reacts with trimethyl phosphite (80°, C6H6) to give 2,2,2-trimethoxy-3,5-diphenyl-4-phenylsulfonyl-1,2-oxa-4-phospholene (II).

     
  2. 2.

    Two processes take place simultaneously at high temperatures (160°): isomerization of phosphorane (II) to give the dimethyl ester of 1,3-diphenyl-2-phenylsulfonyl-3-methoxy-2-propenephosphonic acid (VI), and decomposition of phosphorane (II) to the starting reactants with a cleavage of the P-C bond.

     
  3. 3.

    When phosphorane (II) is reacted with proton-donor reagents the phosphorane ring is opened at the P-O bond to give the dimethyl ester of 1-phenyl-2-benzoyl-2-phenylsulfonylethanephosphonic acid (III).

     
  4. 4.

    Benzylidenephenylsulfonylacetophenone (I) reacts with tris(dimethylamino)phosphine to give the 1∶1 adduct with a bipolar structure (VII) and containing the P-C bond. Its hydrolysis and reaction with dry HCl gas were studied.

     

Keywords

Phosphorane Ester Hydrolysis Adduct Dimethyl 

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Literature cited

  1. 1.
    B. A. Arbuzov, O. D. Zolova, V. S. Vinogradova, and Yu. Yu. Samitov, Dokl. Akad. Nauk SSSR,173, 335 (1967).Google Scholar
  2. 2.
    B. A. Arbuzov, N. A. Polezhaeva, and V. S. Vinogradova, Izv. Akad. Nauk SSSR, Ser. Khim., 2281 (1967).Google Scholar
  3. 3.
    B. P. Arbuzov, E. N. Dianova, V. S. Vinogradova, and M. V. Petrova, Dokl. Akad. Nauk SSSR,195, 1094 (1970).Google Scholar
  4. 4.
    B. A. Arbuzov, T. D. Sorokina, V. S. Vinogradova, and A. A. Musina, Izv. Akad. Nauk SSSR, Ser. Khim., 2727 (1969).Google Scholar
  5. 5.
    B. A. Arbuzov, T. D. Sorokina, and V. S. Vonogradova, Dokl. Akad. Nauk SSSR,177, 1337 (1967).Google Scholar
  6. 6.
    A. Mustafa, M. M. Sidky, S. M. H. D. Zayed, and W. M. Abdo, Tetrahedron,24, 4725 (1968).Google Scholar
  7. 7.
    L. C. Thomas and R. A. Chittenden, Spectrochim. Acta,20, 489 (1964).Google Scholar
  8. 8.
    L. C. Thomas and R. A. Chittenden, Spectrochim. Acta,26A, 781 (1970).Google Scholar
  9. 9.
    G. Kamai and V. A. Kukhtin, Dokl. Akad. Nauk SSSR,102, 283 (1957); Zh. Obshch. Khim.,27, 949 (1957).Google Scholar
  10. 10.
    S. Oae, A. Nakanishi, and S. Kozuka, Tetrahedron,28, 549 (1972).Google Scholar
  11. 11.
    F. Ramirez, A. V. Patwardhan, A. J. Kugler, and C. P. Smith, J. Amer. Chem. Soc.,89, 6276 (1967).Google Scholar
  12. 12.
    F. Ramirez, F. Pilot, and C. P. Smith, Tetrahedron,24, 3735 (1968).Google Scholar
  13. 13.
    J. Troger and O. Beck, J. Prakt. Chem., [2],87, 289 (1913).Google Scholar
  14. 14.
    V. Mark, C. H. Dungan, M. M. Crutchfield, and J. R. Van Wazer, Top. Phosphorus Chem.,5, 294 (1967).Google Scholar
  15. 15.
    F. Bennett, H. Emeleus, and R. Haszeldine, J. Chem. Soc., 3598 (1954).Google Scholar
  16. 16.
    K. Nakanishi, Infrared Absorption Spectra and Structure of Organic Compounds [Russian translation], Mir (1965), p. 46.Google Scholar

Copyright information

© Consultants Bureau 1973

Authors and Affiliations

  • B. A. Arbuzov
    • 1
  • Yu. V. Belkin
    • 1
  • N. A. Polezhaeva
    • 1
  1. 1.A. M. Butlerov Chemical Institute of V. I. Ul'yanov-Lenin Kazan State UniversityUSSR

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