Hydrogen Peroxide → Dibenzylhydroxylamine

Participants

Reaction Steps

U.S. Pat. No. 3,491,151 discloses a method for preparing N,N-dialkylhydroxylamine compounds by allowing hydroxylamines react with alkyl halides, alkyl tosylates or the like. However, this method is also undesirable, because it requires a prolonged reaction time and achieves a yield of no more than about 50%. Tetrahedron Letters, Vol. 37, No. 33 pp. 6025-6028, 1996 discloses a method for synthesizing nitrone compounds by oxidizing dibenzylamine by means of a combination of aqueous hydrogen peroxide and methyltrioxorhenium. According to this synthetic method, an N,N-dibenzylhydroxyl-amine compound is produced in addition to a nitrone compound as a major product. However, its yield is low. Furthermore, the method requires a large amount of methyltrioxorhenium. For these reasons, the method is only disadvantageously applied to practical preparations of N,N-dibenzylhydroxylamine compounds.

Provenance & Evidence