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Geminal systems

64. N-alkoxy-N-chloroureas and N,N-dialkoxyureas

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Abstract

Molecular and crystal structures of N-alkoxy-N-chloroureas and N,N-dialkoxyureas were studied together with those of N-alkoxyureas as reference compounds. N-Alkoxy-N-chloroureas were found to have an elongated N—Cl bond and a shortened N–O(Alk) bond due to the nO(Alk)→σ*N–Cl anomeric effect. Alcoholysis of N-alkoxy-N-chloro derivatives of urea, N′-arylureas, and carbamates in the presence of silver trifluoroacetate leads to sterically hindered N,N-dialkoxyureas, N,N-dialkoxy-N′-arylureas, and N,N-dialkoxycarbamates, respectively.

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Authors and Affiliations

  1. Ukranian State University of Chemical Technology, 8 ul. Gagarina, 49005, Dnepropetrovsk, Ukraine

    V. G. Shtamburg & V. V. Shtamburg

  2. N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    R. G. Kostyanovsky

  3. Kirovograd Flying Academy of the National Aircraft University, 1 ul. Dobrovol’skogo, 25005, Kirovograd, Ukraine

    A. V. Tsygankov

  4. Institute of Single Crystals of the National Academy of Sciences of the Ukraine, 60 ul. Lenina, 61001, Kharkov, Ukraine

    O. V. Shishkin & R. I. Zubatyuk

  5. A. V. Bogatskii Physicochemical Institute of the National Academy of Sciences of the Ukraine, 86 ul. Lyustdorfskaya doroga, 65080, Odessa, Ukraine

    A. V. Mazepa

  6. Dnepropetrovsk State Agrarian University, 25 ul. Voroshilova, 49600, Dnepropetrovsk, Ukraine

    S. V. Kravchenko

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  1. V. G. Shtamburg
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  2. R. G. Kostyanovsky
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  3. A. V. Tsygankov
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  4. V. V. Shtamburg
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  7. A. V. Mazepa
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  8. S. V. Kravchenko
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Correspondence to V. G. Shtamburg.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0062–0075, January, 2015.

For Part 63, see Ref. 1.

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Shtamburg, V.G., Kostyanovsky, R.G., Tsygankov, A.V. et al. Geminal systems. Russ Chem Bull 64, 62–75 (2015). https://doi.org/10.1007/s11172-015-0822-9

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  • DOI: https://doi.org/10.1007/s11172-015-0822-9

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