Journal of the American Chemical Society

Kinetics and mechanism of nucleophilic displacements with heterocyclics as leaving groups. Part 24. Rates and mechanism for the solvolysis of N-tert-alkylpyridinium …

AR Katritzky, B Brycki

Index: Katritzky, Alan R.; Brycki, Bogumil Journal of the American Chemical Society, 1986 , vol. 108, # 23 p. 7295 - 7299

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Citation Number: 30

Abstract

Abstract: Solvolysis rates are measured for I-(I-adamantyl), I-tert-butyl-, and I-(1-methyl-I- phenylethy1) pyridinium cations. Rates are almost independent of solvent and show less variation with the substrate structure than do analogues with leaving groups departing as anions. No evidence is found for any nucleophilic assistance by solvent in the solvolysis of these tert-alkylpyridinium cations. Previously measured solvolysis rates for N-sec- ...