Screening conditions for γ-hydroperoxy-γ-peroxylactone 2a synthesisa.
Entry | Eq. H2O2 | Acid, eq. | Yield 2a, % |
---|---|---|---|
1 | 10 | BF3·Et2O, 10 | 54 |
2 | 10 | SnCl4, 5 | 46 |
3 | 10 | HClO4, 10 | 13 |
4 | 10 | HBF4, 10 | 17 |
5 | 10 | TsOH·H2O, 10 | 24 |
6 | 10 | PMA, 1 | 15 |
7 | 10 | BF3·Et2O, 5 | 38 |
8 | 10 | BF3·Et2O, 2 | 19 |
9b | 10 | BF3·Et2O, 10 | 35 |
10 | 5 | BF3·Et2O, 10 | 53 |
11 | 3 | BF3·Et2O, 10 | 27 |
General procedure: an ethereal solution of H2O2 (4.30 M, 0.698–2.326 mL, 3.0–10.0 mmol, 3.0–10.0 eq.) was added with stirring to a solution of 1a (234.3 mg, 1.00 mmol, 1.0 eq.) in Et2O (3.5 mL). The mixture was cooled to 0 °C and acid was added dropwise with stirring. The reaction mixture was then stirred at 20–25 °C for 24 h.
CH3CN as solvent.