SUPPORTING INFORMATION Oxidation of p-Aminophenols and Formal Radical Cyclization onto Benzene Rings: Formation of Benzo-fused Nitrogen Heterocycles Stephen P. Fletcher, Derrick L. J. Clive,* Jianbiao Peng, and David A. Wingert Chemistry Department, University of Alberta, Edmonton, Alberta, Canada T6G 2G2 e-mail: derrick.clive@ualberta.ca The symbols s, d, t, and q used for 13C NMR indicate 0, 1, 2, or 3 attached hydrogens. Because of restricted rotation many signals were distorted. If "m" appears before s, d, t, or q, this is indicates many signals in close proximity. The use of "br" indicates that the signal is broad. 1-(Trifluoroacetyl)-2,3-dihydro-1H-indol-5-ol (11c). O MeO N CF 3 CO OH N CF 3 CO 11b 11c Compound 11c had: FTIR (CHCl 3 , cast) 3347, 1667, 1616, 1605, 1493, 1462 cm -1 ; 1 H NMR (CD 3 OD, 500 MHz) δ 3.17 (t, J = 8.1 Hz, 2 H), 4.24 (t, J = 8.6 Hz, 2 H), 6.63 (apparent dd, J = 8.8, 2.5 Hz, 1 H), 6.71-6.73 (m, 1 H), 7.92 (d, J = 8.8 Hz, 1 H); 13 C NMR (CD 3 OD, 125 MHz) δ 29.4 (t), 49.4 (t), 112.9 (d), 114.7 (d), 117.8 (s split into q, J CF = 286.0 Hz), 119.6 (d), 135.2 (s), 135.5 (s), 154.5 (s split into q, J CF = 37.1 Hz), 157.2 (s); exact mass m/z calcd for C 10 H 8 F 3 NO 2 231.05072, found 231.05061.