Catalytic Hydrogen Transfer Reduction of Aromatic Nitro Compounds with 4-Vinylcyclohexene

4-비닐시클로헥센을 이용한 방향족 니트로 화합물의 환원반응

  • Received : 1994.06.17
  • Accepted : 1994.07.28
  • Published : 1994.10.01


Most of the aromatic nitro compounds were reduced to amines in high yield by transfer of hydrogen from 4-vinyl cyclohexene to the substrate via palladium catalyst. The usefulness of the method is not affected by the presence of a variety of other functional groups such as -OH, $-OCH_3$, $-CH_3$, $-CO_2H$, and -Cl, except for halogen which is removed during hydrogenation. The reduction of ortho-substituted nitrobenzene such as o-nitrotoluene, o-nitrophenol, o-nitroanisole was slower than the para isomer. Typically, the nitro compound is refluxed in ethanol with a large exess of 4-vinylcyclohexene in the presence of Pd-C catalyst. Under the above conditions, p-nitrobenzaldehyde, p-nitrobenzyl alcohol, and p-nitrobenzyl acetate were reduced to p-toluidine.