Low‐Valent Ruthenium Induced Simultaneous Reduction of Nitro Group and C‐C Double Bond in Nitroolefin 1‐Phenyl‐2‐Nitropropen e‐1

The reduction of 1‐phenyl‐2‐nitropropene‐1 ( 1 ) on using ruthenium complexes was studied in detail in order to correlate this method with those previously recorded in the literature for the hydrogenation of nitroolefins. A variety of products was isolated by varying the reaction temperature and solvent. Among them was 1‐phenyl‐2‐propylamine ( 4 ), completely reduced from the selective both double bond and nitro group. 1‐Phenyl‐2‐propanol ( 5 ) was observed due to reduction of phenylacetone at 125 °C in the presence of ruthenium catalyst. When reaction temperature was lower than 125 °C, by employing RuCl 2 (PPh 3 ) 3 complex, 1‐phenyl‐2‐nitropropane ( 2 ) and phenylacetone ( 3 ) were obtained, respectively. Ru‐BINAP complexes were attempted to produce chiral amine from starting material 1‐phenyl‐2‐nitropropene‐1 ( 1 ).