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Electrophilicities of iminium ions

1997; Elsevier BV; Volume: 38; Issue: 20 Linguagem: Inglês

10.1016/s0040-4039(97)00675-8

1873-3581

Herbert Mayr, Armin R. Ofial,

Organic and Inorganic Chemical Reactions

Rate constants for the reactions of the iminium ions Me2N+CH2 (1), iPr2N+CH2 (2), Ph(Me)N+CH2 (3), and Me2N+C(Cl)H (4) with nucleophiles were determined by 1H-NMR spectroscopy. By correlation, the electrophilicity parameters E(1) = −7.0, E(2) = −8.0, E(3) = −4.8, and E(4) = −5.8 were obtained, which allow to define scope and limitation of aminomethylations.