The manganese-catalyzed carbonylation of amines

Article abstract of DOI:10.1021/ic50025a006

Decacarbonyldimanganese and pentacarbonylmethylmanganese have been found to catalyze the carbonylation of primary aliphatic amines almost exclusively to 1,3-dialkylureas. Ammonia and di-n-butylamine virtually do not react. Aniline reacts very slowly giving 1,3-diphenylurea in low yield. The formation of 1,3-dialkylureas is accompanied by the evolution of hydrogen, so that little or no gas absorption was observed during the reaction. A mechanism of reaction is proposed involving the attack of the amine on an alkylformamide group bonded to the manganese. A simplified procedure for the preparation of decacarbonyldimanganese is also described.