oxygen; 5,15,10,20-tetraphenylporphyrin in chloroform T=-5°C; 0.5 h; Irradiation; Yield given. Yields of byproduct given;

1: tetraphenylporphyrin, O2 / CHCl3 / 0.5 h / -5 °C / Irradiation 2: 64 percent / BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) 0 deg C, 20 min; r.t., 2 h View Scheme

1: tetraphenylporphyrin, O2 / CHCl3 / 0.5 h / -5 °C / Irradiation 2: 64 percent / BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) 0 deg C, 20 min; r.t., 2 h 3: 80 percent / polymer-bound rose bengal, O2 / CH2Cl2 / 1 h / -78 °C / Irradiation View Scheme