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. 2020 May 6;11(20):5313–5322. doi: 10.1039/d0sc01025a

Screening conditions for γ-hydroperoxy-γ-peroxylactone 2a synthesisa.

graphic file with name d0sc01025a-u1.jpg
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
a

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.

b

CH3CN as solvent.