Reactivity of Cage-Like Amines toward p-Toluenesulfonyl Chloride and Diphenyl Chlorophosphate in Acetonitrile |
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| Authors: | Sadovskii Yu S Solomoichenko T N Kas'yan A O Golodaeva E A Anikanova S V Kas'yan L I Savelova V A |
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| Institution: | (1) Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk, Ukraine;(2) Dnepropetrovsk National Universitety, per. Nauchnyi 13, Dnepropetrovsk, 49050, Ukraine;(3) Institut fur organische Chemie, Rheinisch-Westfalische technische Hochschule, Aachen, Germany |
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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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