Cyclohexene → 2,2,5,5-Tetramethyl-3-(4-nitrophenyl)-4-(4-aminophenyl)hex-3-ene

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A solution of 0.62 g 2,2,5,5-tetramethyl-3,4-di(4-nitrophenyl)hex-3-ene,2.6 g cyclohexene and 1.4 g 10% Pd/C in THF was refluxed for 2 hrs. The Pd/C was removed by filtration and the residue after evaporation of the solvent was purified by chromatography on silica gel (25% CH2Cl2 -hexane) to give 0.285 g (50%) 2,2,5,5-tetramethyl-3-(4-nitrophenyl)-4-(4-aminophenyl)hex-3-ene: 1H NMR (CDCl3): δ0.66 (s, 8H), 0.70 (s, 8H), 3.61 (s, 2H), 6.61-6.63 (d, 2H), 7.30-7.34 (d, 2H), 8.12-8.14 (d, 2H): 13C NMR (CDCl3): δ32.81, 32.84, 37.59, 38.16, 113.58, 121.93, 131.34, 131.48, 133.12, 143.78, 144.58, 146.22, 146.88, 152.11.

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