1.1: 94 percent / pyridinium chlorochromate / CH2Cl2 2.1: 93 percent / methanol 3.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 4.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 5.1: 98 percent / LiAlH4 / tetrahydrofuran 6.1: pyridinium chlorochromate / CH2Cl2 7.1: tetrahydrofuran / -78 °C 8.1: 93 percent / NaH / tetrahydrofuran 9.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 10.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 11.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 12.1: 84 percent / pyridinium chlorochromate / CH2Cl2 13.1: p-TsOH; HOCH2CH2OH / toluene / Heating 13.2: p-TsOH; H2O / acetone / Heating 13.3: Et3SiH; CF3CO2H / benzene 14.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 2.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 3.1: 98 percent / LiAlH4 / tetrahydrofuran 4.1: pyridinium chlorochromate / CH2Cl2 5.1: tetrahydrofuran / -78 °C 6.1: 93 percent / NaH / tetrahydrofuran 7.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 8.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 9.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 10.1: 84 percent / pyridinium chlorochromate / CH2Cl2 11.1: p-TsOH; HOCH2CH2OH / toluene / Heating 11.2: p-TsOH; H2O / acetone / Heating 11.3: Et3SiH; CF3CO2H / benzene 12.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 94 percent / pyridinium chlorochromate / CH2Cl2 2.1: NaH / tetrahydrofuran 3.1: t-BuOK / tetrahydrofuran 4.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 5.1: 94 percent / pyridinium chlorochromate / CH2Cl2 6.1: 93 percent / methanol 7.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 8.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 9.1: 98 percent / LiAlH4 / tetrahydrofuran 10.1: pyridinium chlorochromate / CH2Cl2 11.1: tetrahydrofuran / -78 °C 12.1: 93 percent / NaH / tetrahydrofuran 13.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 14.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 15.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 16.1: 84 percent / pyridinium chlorochromate / CH2Cl2 17.1: p-TsOH; HOCH2CH2OH / toluene / Heating 17.2: p-TsOH; H2O / acetone / Heating 17.3: Et3SiH; CF3CO2H / benzene 18.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 94 percent / HCl; MeOH 2.1: 94 percent / pyridinium chlorochromate / CH2Cl2 3.1: NaH / tetrahydrofuran 4.1: t-BuOK / tetrahydrofuran 5.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 6.1: 94 percent / pyridinium chlorochromate / CH2Cl2 7.1: 93 percent / methanol 8.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 9.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 10.1: 98 percent / LiAlH4 / tetrahydrofuran 11.1: pyridinium chlorochromate / CH2Cl2 12.1: tetrahydrofuran / -78 °C 13.1: 93 percent / NaH / tetrahydrofuran 14.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 15.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 16.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 17.1: 84 percent / pyridinium chlorochromate / CH2Cl2 18.1: p-TsOH; HOCH2CH2OH / toluene / Heating 18.2: p-TsOH; H2O / acetone / Heating 18.3: Et3SiH; CF3CO2H / benzene 19.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1.1: 77 percent / 2,3-dichloro-5,6-dicyanobenzoquinone; H2O / CH2Cl2 2.1: 94 percent / pyridinium chlorochromate / CH2Cl2 3.1: 93 percent / methanol 4.1: 90 percent / Grubbs' catalyst / CH2Cl2 / Heating 5.1: 93 percent / TMS-OTf / CH2Cl2 / -78 - 0 °C 6.1: 98 percent / LiAlH4 / tetrahydrofuran 7.1: pyridinium chlorochromate / CH2Cl2 8.1: tetrahydrofuran / -78 °C 9.1: 93 percent / NaH / tetrahydrofuran 10.1: 86 percent / BuSnH; 2,2'-azobisisobutyronitrile / toluene / Heating 11.1: 98 percent / m-chloroperbenzoic acid; NaHCO3 / CH2Cl2 12.1: 64 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C 13.1: 84 percent / pyridinium chlorochromate / CH2Cl2 14.1: p-TsOH; HOCH2CH2OH / toluene / Heating 14.2: p-TsOH; H2O / acetone / Heating 14.3: Et3SiH; CF3CO2H / benzene 15.1: 84 percent / BBr3 / CH2Cl2 / -30 - 0 °C View Scheme

1: 26 percent / (PhSeO)2O, NaHCO3 / benzene / 20 h / Heating 2: n-Bu4NF / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 78 percent / 1-methyl-4-piperidone, (i-PrO)3Al / toluene / 4 h / Heating 2: 96 percent / p-TsOH / diethyl ether / Ambient temperature View Scheme

Fe(III)PFP(O2(2-)); 18-crown-6 ether in acetonitrile 72 h; Ambient temperature; Product distribution;

sodium methylate in N,N-dimethyl-formamide T=20°C; 2 h; regeneration reactions of the parent compound from different perfluoroaryl derivatives to the alcohols; other educts and products, different times, temperatures and mol ratios of the educts; Product distribution;

2: Irradiation View Scheme