Grubb's 2nd generation catalyst in dichloromethane T=40°C; 4 h;

1: DMAP; dicyclohexylcarbodiimide / CH2Cl2 / 20 °C 2: 65 percent / PhCH=Ru[(Mes)NCH2CH2N(Mes)]CH(PCy3)Cl2 / CH2Cl2 / 4 h / 40 °C View Scheme

1: 92 percent / SnCl4 / CH2Cl2 / 1.) -78 deg C, 2.) room temperature 2: 78 percent / KOH / methanol; H2O / Heating 3: 90 percent / Et3N / CH2Cl2 4: 96 percent / H2O2 / tetrahydrofuran / Ambient temperature 5: 1.) NaIO4 / 2.) pyrolysis View Scheme

1: 90 percent / Et3N / CH2Cl2 2: 96 percent / H2O2 / tetrahydrofuran / Ambient temperature 3: 1.) NaIO4 / 2.) pyrolysis View Scheme

1: 78 percent / KOH / methanol; H2O / Heating 2: 90 percent / Et3N / CH2Cl2 3: 96 percent / H2O2 / tetrahydrofuran / Ambient temperature 4: 1.) NaIO4 / 2.) pyrolysis View Scheme

1: 96 percent / H2O2 / tetrahydrofuran / Ambient temperature 2: 1.) NaIO4 / 2.) pyrolysis View Scheme

sodium periodate 2.) pyrolysis; Yield given. Multistep reaction;