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Substituent effects on the13C and17O NMR, IR, and UV spectral parameters for propynals

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

Conclusions

Trialkylsilyl(germanyl)propynals show a lower triple bond polarization compared with their carbon analogs because of the electron acceptor effects of the R substituents and the aldehyde group. This increases the inertness of the C≡C bond towards nucleophiles (RSH, R2NH) and lowers the regioselectivity of dipolar attack. Lowering the relative basicity of the substituted propynals decreases the integrated intensity of the C=0 absorption band and shifts the δ17O signal to low field.

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Literature cited

  1. A. S. Medvedeva, M. M. Demina, A. I. Borisova, et al., J. Organomet. Chem.,241, 109 (1982).

    Google Scholar 

  2. A. S. Medvedeva, O. I. Margorskaya, M. M. Demina, et al., Zh. Obshch. Khim.,53, 2247 (1983).

    Google Scholar 

  3. A. I. Borisova, A. S. Medvedeva, I. D. Kalikhman, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 2640 (1985).

  4. A. I. Borisova, M. M. Demina, A. S. Medvedeva, and N. S. Vyazankin, Zh. Obshch. Khim.,53, 1310 (1983).

    Google Scholar 

  5. A. S. Medvedeva, A. I. Borisova, M. M. Demina, et al., Zh. Obshch. Khim.,52, 2554 (1982).

    Google Scholar 

  6. A. I. Borisova, A. S. Medvedeva, O. B. Bannikova, and N. S. Vyazankin, Izv. Akad. Nauk SSSR, Ser. Khim., 1403 (1985).

  7. E. V. Arshavskaya, L. D. Lezhava, and A. M. Sladkov, Izv. Akad. Nauk SSSR, Ser. Khim., 200 (1979).

  8. A. G. Proidakov, G. A. Kalabin, R. G. Mirskov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 94 (1978).

  9. G. A. Kalabin, A. G. Proidakov, L. D. Gavrilov, and L. I. Vereshchagin, Zh. Org. Khim., 493 (1977).

  10. D. Rosenberg and W. Drenth, Tetrahedron,27, 3893 (1971).

    Google Scholar 

  11. A. N. Egorochkin, O. I. Margorskaya, S. E. Skobeleva, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1789 (1986).

  12. M. M. Demina, A. S. Medvedeva, N. I. Protsuk, and N. S. Vyazankin, Zh. Obshch. Khim.,48, 1563 (1978).

    Google Scholar 

  13. A. I. Borisova, A. S. Medvedeva, and N. S. Vyazankin, Russian Patent 715580 SSSR; Byull. Izobr., No. 9, 6 (1980).

  14. A. S. Medvedeva, L. P. Safronova, and M. G. Voronkov, Izv. Akad Nauk SSSR, Ser. Khim., 121 (1976).

  15. G. Levy and G. Nelson, Progress in13C NMR, Wiley-Interscience, New York (1972).

    Google Scholar 

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Authors and Affiliations

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

    A. S. Medvedeva, O. I. Margorskaya, I. D. Kalikhman, N. I. Golovanova, N. I. Shergina & N. S. Vyazankin

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  1. A. S. Medvedeva
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  2. O. I. Margorskaya
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  3. I. D. Kalikhman
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  4. N. I. Golovanova
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  5. N. I. Shergina
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  6. N. S. Vyazankin
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 321–325, February, 1988.

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Medvedeva, A.S., Margorskaya, O.I., Kalikhman, I.D. et al. Substituent effects on the13C and17O NMR, IR, and UV spectral parameters for propynals. Russ Chem Bull 37, 246–249 (1988). https://doi.org/10.1007/BF00957419

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  • DOI: https://doi.org/10.1007/BF00957419

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