NEW METHOD FOR THE SYNTHESIS OF NONSYMMETRIC DINUCLEATING LIGANDS BY AMINOMETHYLATION OF PHENOLS AND SALICYLALDEHYDES

被引：48

作者：

LUBBEN, M ^{[1
]}

FERINGA, BL ^{[1
]}

机构：

[1] UNIV GRONINGEN,GRONINGEN CTR CATALYSIS & SYNTH,DEPT ORGAN & MOLEC INORGAN CHEM,9747 AG GRONINGEN,NETHERLANDS

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 08期

关键词：

D O I：

10.1021/jo00087a046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monoaminomethylated phenols 5-7 and symmetrically diaminomethylated phenols 8 and 9 were prepared in a one-step procedure-from p-cresol, formaldehyde, and a variety of secondary amines by making use of the aromatic Mannich reaction. Nonsymmetric diaminomethylated phenols 10 and 11 were prepared by a sequential aromatic Mannich reaction using p-cresol, formaldehyde, and two different secondary amines. Alternatively, nonsymmetric diaminomethylated phenols 20-24 were prepared by aminomethylation of 5-methylsalicylaldehyde followed by Ca) condensation with a primary amine and subsequent reduction or (b) reductive amination with a secondary amine. Monoami-nomethylated and (non)symmetric diaminomethylated phenols are excellent ligands for the synthesis of mono- and dinuclear transition metal complexes as is illustrated by the isolation of mononuclear iron(III) complex 25 and nonsymmetric dinuclear copper(II) complex 26.

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页码：2227 / 2233

页数：7

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