Table 1 Ring-opening reactions of hetero[3.1.1]propellanesa

From: Hetero[3.1.1]propellanes

  1. Reaction conditions: aBEt3 (10 mol%) in Et2O, 25 °C (for 18a, 18b, 18d–f and 18n); bIr(ppy)3 (2.5 mol%), tBuCN, blue LEDs (450–456 nm), 25 °C (for 18a, 18c, 18e, 18g–l and 18ab–ad); cdirect reaction with organohalide with no initiator; diodomethylaziridine, Ir(ppy)3 (2.5 mol%), tBuCN, blue LEDs (450–456 nm), 25 °C; eRSO2Br, Et2O, 25 °C; fRSO2I, −5 °C, 10 min; gI2, 25 °C; hN-phenylpyrrolidine, 4CzIPN (2.5 mol%), blue LEDs (440 nm), dimethylacetamide, 25 °C; ichalcogen or dichalcogen, 25 °C; jcysteine derivative, BEt3 (10 mol%). The structure of 18i was determined using single-crystal X-ray diffraction (CCDC 2412511, displacement ellipsoids drawn at 50%).
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