Absolute Ethanol Reflux. 1h H HO R H2n NH2 R=H OMe. NO or Cl Starting Materials: Salicy aldehyde Derivatives Diamines OH O OH O OH O OH O H2n NH2 H2N NH FW=156.57FW=167.12FW=152.15FW=122.12 FW=114.19FW=60.10 d=1.219 d=1.146 d=0951 d=0899 2. Making the mn(salen) Complex (eq 3) Some of our salen ligands behave a little differently than the ones Jacobsen describes. For some cases toluene needs to be added to the hot ethanol solution to dissolve the ligand. After the reaction is complete, it is crucial to cool the solution down to promote the precipitation of the Mn(salen)complex. It's easiest to put the flask in an ice-bath for about an hour, then filter the mixture. If no solids form after the ice-bath cooling, it may be necessary to leave the solution in the fridge overnight. Air. Ethanol. Reflux. 1h oh Ho 2. LiCl Reflux. 30 minOH O Absolute Ethanol N N H (2) Reflux, 1h R H2N NH2 R OH HO R R = H, OMe, NO2, or Cl Starting Materials: Salicylaldehyde Derivatives: Diamines: OH O OH O OH O OH O H H H H H2N NH2 H2N NH2 Cl NO2 OMe FW = 156.57 FW = 167.12 FW = 152.15 FW = 122.12 FW = 114.19 FW = 60.10 d = 1.219 d = 1.146 d = 0.951 d = 0.899 2. Making the Mn(salen) Complex (eq 3) • Some of our salen ligands behave a little differently than the ones Jacobsen describes. For some cases toluene needs to be added to the hot ethanol solution to dissolve the ligand. • After the reaction is complete, it is crucial to cool the solution down to promote the precipitation of the Mn(salen) complex. It's easiest to put the flask in an ice-bath for about an hour, then filter the mixture. If no solids form after the ice-bath cooling, it may be necessary to leave the solution in the fridge overnight. 1. Mn(OAc)2·4H2O Air, Ethanol, Reflux, 1h N N N N (3) Mn 2. LiCl, Reflux, 30 min R OH HO R R O O R Cl 39