Reactivity of cage-like amines toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile

YS Sadovskii, TN Solomoichenko, AO Kas' yan…

Index: Sadovskii; Solomoichenko; Kas'yan; Golodaeva; Anikanova; Savelova Russian Journal of Organic Chemistry, 2004 , vol. 40, # 1 p. 50 - 56

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Abstract

Abstract The nucleophilic reactivity of amines of the norbornane, norbornene, and adamantane series toward p toluenesulfonyl 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 ...