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Reactivity of Cage-Like Amines toward p-Toluenesulfonyl Chloride and Diphenyl Chlorophosphate in Acetonitrile

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Abstract

The nucleophilic reactivity of amines of the norbornane, norbornene, and adamantane series toward ptoluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile at 25°C is determined mainly by the steric factor. Parameters characterizing spatial accessibility of the reaction center in the amine molecule have been determined. Cage-like substituents show no appreciable effect on the amine reactivity, as compared to common alkyl groups.

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk, Ukraine

    Yu. S. Sadovskii, T. N. Solomoichenko, E. A. Golodaeva, S. V. Anikanova & V. A. Savelova

  2. Dnepropetrovsk National Universitety, per. Nauchnyi 13, Dnepropetrovsk, 49050, Ukraine

    A. O. Kas'yan

  3. Institut fur organische Chemie, Rheinisch-Westfalische technische Hochschule, Aachen, Germany

    L. I. Kas'yan

Authors
  1. Yu. S. Sadovskii
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  2. T. N. Solomoichenko
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  3. A. O. Kas'yan
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  4. E. A. Golodaeva
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  5. S. V. Anikanova
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  6. L. I. Kas'yan
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  7. V. A. Savelova
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Sadovskii, Y.S., Solomoichenko, T.N., Kas'yan, A.O. et al. Reactivity of Cage-Like Amines toward p-Toluenesulfonyl Chloride and Diphenyl Chlorophosphate in Acetonitrile. Russian Journal of Organic Chemistry 40, 50–56 (2004). https://doi.org/10.1023/B:RUJO.0000034909.58849.e9

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  • DOI: https://doi.org/10.1023/B:RUJO.0000034909.58849.e9

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