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Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters

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Abstract

Treatment of an alcoholic suspension of amino acids with trimethylchlorosilane yielded phenylglycine, valine, β-phenylalanine, and homovaline ester hydrochlorides. Their saccharin-catalyzed silylation with hexamethyldisilazane proceeds quantitatively and involves only one proton of the amino group. The best conversion of the amino acid esters to the corresponding isocyanates was achieved by phosgene treatment of their monosilyl urethanes, rather than of the silylated amino esters. Monosilyl urethanes are formed quantitatively by treatment of the amino acid ester hydrochlorides with the hexamethyldisilazane-CO2 system. The 1H NMR spectra show that monosilyl urethanes derived from α-and β-amino acid esters are characterized by intramolecular interaction of the silicon atom and the oxygen atom of the carboxy group.

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References

  1. Lebedev, A.V., Lebedeva, A.B., Sheludyakov, V.D., Ovcharuk, S.N., Kovaleva, E.A., and Ustinova, O.L., Zh. Obshch. Khim., 2006, vol. 76, no. 7, p. 1118.

    Google Scholar 

  2. Bruynes, S.A. and Jurriens, T.K., J. Org. Chem., 1982, vol. 47, no. 20, p. 3966.

    Article  CAS  Google Scholar 

  3. Davidovich, Yu.A., Butaeva, V.I., Galkin, O.M., Sentsova, T.N., and Rogozhin, S.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1977, no. 7, p. 1682.

  4. Mironov, V.F. and Kozyukov, V.P., Zh. Obshch. Khim., 1984, vol. 54, no. 6, p. 1217.

    CAS  Google Scholar 

  5. Lebedev, A.V., Lebedeva, A.B., Sheludyakov, V.D., Ovcharuk, S.N., Kovaleva, E.A., and Ustinova, O.L., Zh. Obshch. Khim., 2006, vol. 76, no. 3, p. 493.

    Google Scholar 

  6. Sheludyakov, V.D., Gusev, A.I., Dmitrieva, A.B., Los’, M.G., and Kirilin, A.D., Zh. Obshch. Khim., 1983, vol. 53, no. 10, p. 2276.

    CAS  Google Scholar 

  7. Sheludyakov, V.D., Dmitrieva, A.B., Gusev, A.I., Apal’kova, G.M., and Kirilin, A.D., Zh. Obshch. Khim., 1984, vol. 54, no. 10, p. 2298.

    CAS  Google Scholar 

  8. Sheludyakov, V.D., Lebedeva, A.B., Kisin, A.V., Nikishina, I.S., Lebedev, A.V., and Kirilin, A.D., Zh. Obshch. Khim., 1988, vol. 58, no. 2, p. 393.

    CAS  Google Scholar 

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Authors and Affiliations

  1. State Research Institute of Chemistry and Technology of Organoelement Compounds, shosse Entuziastov 38, Moscow, 111123, Russia

    A. V. Lebedev, A. B. Lebedeva, V. D. Sheludyakov, V. V. Shatunov & S. N. Ovcharuk

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  1. A. V. Lebedev
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  2. A. B. Lebedeva
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  3. V. D. Sheludyakov
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  4. V. V. Shatunov
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  5. S. N. Ovcharuk
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Original Russian Text © A.V. Lebedev, A.B. Lebedeva, V.D. Sheludyakov, V.V. Shatunov, S.N. Ovcharuk, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 4, pp. 622–626.

For communication III, see [1].

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Lebedev, A.V., Lebedeva, A.B., Sheludyakov, V.D. et al. Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters. Russ J Gen Chem 77, 581–585 (2007). https://doi.org/10.1134/S1070363207040135

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  • DOI: https://doi.org/10.1134/S1070363207040135

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