A Novel Beckmann Fission Reaction of 2-Aminocyclohexanone Oxime

Article abstract of DOI:10.1246/bcsj.57.895

2-(4-Cyanobutyl)-4,5,6,7-tetrahydrobenzimiazole was obtained by treating 2-aminocyclohexanone oxime with ethyl acetimidate hydrochloride in acetic acid at below 50 deg C, though only 2-methyl-4,5,6,7-tetrahydrobenzimidazole was produced by the reaction of 2-aminocyclohexanone oxime and free ethyl acetimidate in neutral solvents.A novel Beckmann fission reaction of dimeric 2-aminocyclohexanone oxime is presumed to participate in the formation of 2-(4-cyanobutyl)-4,5,6,7-tetrahydrobenzimidazole.