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Reactions of aromatic aldehydes with trialkylsilanes in presence of metal chlorides

  • N. E. Glushkova
  • N. P. Kharitonov
Organic and Biological Chemistry

Conclusions

  1. 1.

    A study was made of the reactions of benzaldehyde, p-t-butylbenzaldehyde, and p-(trimethyl-silyl)benzaldehyde with trialkylsilanes in presence of Zn, Sn, and Ni chlorides. In presence of ZnCl2 and SnCl2 the addition of the trialkylsilanes to the carbonyl group of the aromatic aldehyde occurs. In presence of NiCl2, as well as addition, the formation of α,α'-bis(trialkylsiloxy)bibenzyls occurs.

     
  2. 2.

    p-t-Butylbenzaldehyde shows the greatest tendency to form addition products with trialkylsilanes, and p-(trimethylsilyl)benzaldehyde shows the greatest tendency to form siloxy derivatives of bibenzyl.

     
  3. 3.

    The tendency for a trialkylsilane to add at the carbonyl group of the aromatic aldehyde increases with increase in the length of the alkyl group in the trialkylsilane.

     
  4. 4.

    Fourteen previously undescribed trialkyl (benzyloxy)silanes and α,α'-bis(trialkoxysiloxy)bibenzyls were synthesized.

     

Keywords

Chloride Silane Aldehyde Carbonyl Carbonyl Group 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    B. N. Dolgov, N. E. Glushkova, and N. P. Kharitonov, Izv. AN SSSR. Otd. khim. n.,1960, 351.Google Scholar
  2. 2.
    B. N. Dolgov, N. E. Glushkova, and N. P. Kharitonov, Izv. AN SSSR. Otd. khim. n.,1961, 1069.Google Scholar
  3. 3.
    N. E. Glushkova and N. P. Kharitonov, Izv. AN SSSR. Ser. khim.,1964, 78.Google Scholar
  4. 4.
    A. Zappel, J. Amer. Chem. Soc.,77, 4228 (1955).Google Scholar
  5. 5.
    E. G. Rochow and K. Gingold, J. Amer. Chem. Soc.,76, 4852 (1954).Google Scholar
  6. 6.
    C. Krüger, E. G. Rochow, and U. Wannaget, Chem. Ber.,96, 2132 (1963).Google Scholar
  7. 7.
    H. Kautsky, H. Keek, and H. Kunze, Z. Naturforsch.,96, 165 (1954).Google Scholar
  8. 8.
    B. N. Dolgov, Yu. I. Khudobin, and N. P. Kharitonov, Trans. of Conference: “Chemistry and Practical Application of Organosilicon Compounds” [in Russian], TsBTI, Leningrad, No. 1, 220 (1958).Google Scholar
  9. 9.
    A. E. Chichibabin, S. A. Elgazin, and V. A. Lengol'd, Zh. russk. fiz.-khim. obshch.,60, 347 (1928).Google Scholar
  10. 10.
    M. B. Turova-Polyak and N. P. Dobrosel'skaya, Zh. obshch. khimii,29, 1072 (1959).Google Scholar
  11. 11.
    B. N. Dolgov, N. P. Kharitonov, and M. G. Voronkov, Zh. obshch. khimii,24, 1178 (1954).Google Scholar
  12. 12.
    B. N. Dolgov, Yu. I. Khudobin, and N. P. Kharitonov, Izv. AN SSSR. Otd. khim. n.,1959, 1238.Google Scholar
  13. 13.
    Yu. V. Karyakin, Pure Chemical Reagents [in Russian], Goskhimizdat, Moscow (1947).Google Scholar
  14. 14.
    A. V. Topchiev and G. M. Panchenkov, et al., Trans. of Conference: “Chemistry and Practical Application of Organosilicon Compounds” [in Russian], TsBTI, Leningrad, No. 3, 92 (1958).Google Scholar

Copyright information

© Consultants Bureau 1967

Authors and Affiliations

  • N. E. Glushkova
    • 1
  • N. P. Kharitonov
    • 1
  1. 1.I. V. Grebenshchikov Institute of Silicate ChemistryAcademy of Sciences of the USSRUSSR

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