Nucleophilic addition to ferrocenyl-stabilized carbocations: a test of the generality of the N+-correlation

Abstract

Rate constants for reactions of p-MeOC₆H₄-C⁺HFc (1)(Fc = ferrocenyl) in water and of (1) and Fc₂C⁺H in water–acetonitrile with neutral and anionic nucleophiles have been measured; the data are only approximately correlated by the Ritchie N₊-relationship and comparison of the rate constants for reactions of (1) and of (p-MeOC₆H₄)₃C⁺ in water with nucleophiles suggests that reactions of the latter with bulky amines are subject to steric hindrance.