Hypervalent iodine oxidation of amines using iodosobenzene: Synthesis of nitriles, ketones and lactams

Primary aliphatic amines on oxidation with iodosobenzene in CH2Cl2 or H2O yield the corresponding nitriles, while primary cycloalkylamines give the corresponding cyclic ketones. Lactams are obtained by the oxidation of cyclic amines. (S)(−) Nicotine (15) is oxidized to (+)-cotinine (16). The intermediary imine involved in these processes was trapped in the case of piperidine as the α-aminonitrile.