Metal Carbonyl-Induced N–O Bond Cleavage of the Oxime Group

Abstract The reaction of [Mo(CO)6] or [Fe2(CO)9] with oxime O-acetate of 1,3-diphenyl-2-propen-1-one undergoes a reductive N–O bond cleavage to give an imine which dimerises and/or is hydrolyzed to ketones. The dimer, so formed, undergoes fragmentations to give pyridine and pyrimidine derivatives. Similarly, the reaction of [Mo(CO)6] with several oxime O-acetates, oximes, and an oxime ether were shown to give the corresponding ketones. A reaction of oxime O-acetates with [Cr(CO)6] or with [W(CO)6] to give the corresponding ketones was also shown to proceed very slowly.