Table 3.

Preparation of Monocyclic Arene Oxides (l3)^a

^aStandard reaction conditions. Step 1: MTAD (7, 1.0 mmol, 1.0 equiv), arene (9, 10 mmol, 10 equiv), EtCN (0.1 M), visible light, −78 °C, 12 h; then addition of Mn(ClO₄)₂/phenanthroline (25/50 mol %) in MeCN and CH₃CO₃H (3.0 mmol, 3.0 equiv), −78 °C, 2 h. Step 2: epoxide 8 (0.2 mmol, 1.0 equiv), KOH (2.0 mmol, 10 equiv), 40 °C, 2 h; then workup and exposure of crude to Ni₂O₃ (0.6 mmol, 3.0 equiv), CDO₃ (0.1 M), 0 °C, 1 min. Reported yields of 8 (step 1) are of isolated products and the ratio of diastereoisomers and constitutional isomer (bracket) were determined by ¹H NMR of the crude reaction mixtures. Reported yields of 13 (step 2) are based on ¹H NMR integration relative to the internal standard (MeNO₂).