2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene in water; acetonitrile T=0 - 20°C; Jones Oxidation; 22.5 h;

1: 96 percent / 4 h / Ambient temperature 2: NaIO4, Ru2O / acetonitrile; CHCl3; H2O / Ambient temperature View Scheme

1: 78 percent / thionyl chloride / methanol / 2 h / Ambient temperature 2: 99 percent / bis(triphenylphosphine)palladium dichloride, CuI, Et3N / dimethylformamide / 2 h / 70 °C 3: 80 percent / NH3 / methanol / 3 h / 80 °C 4: 96 percent / 80percent aq. TFA / 2 h / Ambient temperature View Scheme

1: 85 percent / 50percent aq. HCOOH / 1.5 h / 80 °C 2: 65 percent / SOCl2 / Ambient temperature 3: 85 percent / -20 - 20 °C View Scheme