Anilines are oxidized to azobenzenes in methanol or methylene chloride solution using dioxygen as the oxidant and bis(salicylaldehyde)ethylenediimine cobalt(II) (CoIIsalen) as catalyst. In the presence of carbon monoxide, isocyanates, urethanes and ureas are also obtained. The latter two are the only reaction products when the aliphatic amine 1-adamantylamine is used as a substrate. Increasing the pressures of dioxygen and carbon monoxide significantly improves reaction yields. Ortho-aminophenol give the corresponding azo derivative and an oxazolone. Aromatic secondary amines give secondary formamides in low yields.
The bis(salicylaldehyde ethylenediimine)cobalt(II)-catalyzed oxidative carbonylation of primary and secondary amines / F. Benedini, M. Nali, B. Rindone, S. Tollari, S. Cenini, G. LA MOnica, F. Porta. - In: JOURNAL OF MOLECULAR CATALYSIS. - ISSN 0304-5102. - 34:2(1986), pp. 155-161.
The bis(salicylaldehyde ethylenediimine)cobalt(II)-catalyzed oxidative carbonylation of primary and secondary amines
F. Porta
1986
Abstract
Anilines are oxidized to azobenzenes in methanol or methylene chloride solution using dioxygen as the oxidant and bis(salicylaldehyde)ethylenediimine cobalt(II) (CoIIsalen) as catalyst. In the presence of carbon monoxide, isocyanates, urethanes and ureas are also obtained. The latter two are the only reaction products when the aliphatic amine 1-adamantylamine is used as a substrate. Increasing the pressures of dioxygen and carbon monoxide significantly improves reaction yields. Ortho-aminophenol give the corresponding azo derivative and an oxazolone. Aromatic secondary amines give secondary formamides in low yields.Pubblicazioni consigliate
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