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Synthesis, crystal and molecular structures, and steroechemical nonrigidity ofN-(chlorodimethylgermylmethyl)-andN-(bromodimethylgermylmethyl)-N-[(S)-1-phenylethyl]acetamides andN-(chlorodimethylgermylmethyl)-4-phenyl-2-pyrrolidone

  • Organometallic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

RacemicN-(chlorodimethylgermylmethyl)-4-phenyl-2-pyrrolidone and the first optically active amide derivatives containing the asymmetrical carbon atom and the five-coordinate germanium atom,viz.,N-(chlorodimethylgermylmethyl)- andN-(bromodimethylgermyl-methyl)-N-[(S)-1-phenylethyl] acetamides, were synthesized. Their structures were established by X-ray diffraction analysis. The geometric characteristics of the trigonal-bipyramidal valence environment about the germanium atoms are compared with those of analogous enantiomeric silicon compounds and the related five-coordinate germanium compounds. The barriers to permutational isomerization of the title compounds were determined by dynamic1H NMR spectroscopy. It was found that these barriers are higher than those of the corresponding silicon analogs.

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Authors and Affiliations

  1. Russian State Medical University, 1 ul. Ostrovityanova, 117869, Moscow, Russian Federation

    S. Yu. Bylikin, Vad V. Negrebetsky, A. G. Shipov & Yu. I. Baukov

  2. V. I. Lenin Moscow State Pedagogical University, 1 ul. M. Pirogovskaya, 119891, Moscow, Russian Federation

    S. A. Pogozhikh

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    V. N. Khrustalev & Yu. E. Ovchinnikov

Authors
  1. S. Yu. Bylikin
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  2. S. A. Pogozhikh
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  3. V. N. Khrustalev
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  4. Vad V. Negrebetsky
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  5. A. G. Shipov
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  6. Yu. E. Ovchinnikov
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  7. Yu. I. Baukov
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 137–144, January, 2000.

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Bylikin, S.Y., Pogozhikh, S.A., Khrustalev, V.N. et al. Synthesis, crystal and molecular structures, and steroechemical nonrigidity ofN-(chlorodimethylgermylmethyl)-andN-(bromodimethylgermylmethyl)-N-[(S)-1-phenylethyl]acetamides andN-(chlorodimethylgermylmethyl)-4-phenyl-2-pyrrolidone. Russ Chem Bull 49, 140–147 (2000). https://doi.org/10.1007/BF02499080

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  • DOI: https://doi.org/10.1007/BF02499080

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