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NAD(P)H models XXII. Magnesium ion mediated acid catalysis of the reduction of imines by Hantzsch ester

1986; Royal Netherlands Chemical Society; Volume: 105; Issue: 9 Linguagem: Inglês

10.1002/recl.19861050906

1878-7096

Johannes C.G. Van Niel, C. W. F. Kort, U. K. PANDIT,

Inorganic and Organometallic Chemistry

Abstract Reduction of imines ( 2a‐e ) derived from n ‐butylamine and p ‐substituted benzaldehydes, in the presence of magnesium perchlorate, by Hantzsch ester ( 1 ), in acetonitrile, proceeds via the corresponding iminium salts formed by protonation of the imines by [Mg(H 2 O)L 5 ] 2+ complexes. These complexes are produced by reaction of Mg 2+ ions with water, which is associated with the solvent acetonitrile. Within the range 1.67 × 10 −3 ‐26.11 × 10 −3 M of added water, the rate of the reaction shows a direct dependence upon the concentration of water. Rates of reduction of the iminium perchlorates of 2a‐e exhibit a Hammett relationship with a ρ value of + 1.83.