论文信息 - Effects of Metal Ions on Reactivity Patterns in the Reactions of 1-Methoxycarbonyl-2-imidazolidinone and Its Derivatives with Butylamine

Effects of Metal Ions on Reactivity Patterns in the Reactions of 1-Methoxycarbonyl-2-imidazolidinone and Its Derivatives with Butylamine

The reactions of 1-methoxycarbonyl-2-imidazolidinone, 3-acetyl-1-methoxycarbonyl-2-imidazolidinone and 1-methoxycarbonyl-cis-perhydrocyclopenta[d]imidazol-2-one with butylamine were studied in the absence and presence of various metal ions. Certain bivalent ions such as Mg2+, Ca2+, and Mn2+ enhanced an electrophilic reactivity of the methoxycarbonyl group and facilitated the transfer reaction of this group to butylamine, especially when the imidazolidinone moiety of substrates bears the methoxycarbonyl group at one N-position and a hydrogen atom at the other N-position. Whereas monovalent ions such as Na+ and Ag+, and bivalent ions such as Zn2+ and Cu2+, had no appreciable effect on the reactivity, and exhibited almost the same reactivity patterns as those observed in the reactions in the absence of metal ions. A possible explanation is given in terms of the stability of coordination complexes which are formed by the interaction between the imidazolidinone moiety of substrates and added ions.

H. Kawai | E. Imoto | Y. Otsuji | N. Matsumura

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