Table 2.
Fragmentation of hydroperoxyacetals with t-BuOCl
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|---|---|---|---|---|---|
| Entry | Substrate | t-BuOCl (eq) | t(min) | Product | Yielda |
| 1 | 1a | 1.2 | 10 | 2a | 77% |
| 2b | 1a | 1.2 | 10 | 2a | 77% |
| 3c | 1a | 1.2 | 10 | 2a | 79% |
| 4d | 1a | 1.2 | 10 | 2a | 84% |
| 5 | 1a | 0.25 | 15 | 2a | 78% |
| 6 | 1b | 1.2 | 10 | 2b | 85% |
| 7 | 1d | 1.2 | 10 | 2d | 84% |
| 8 | 1e | 0.25 | 15 | 2e | 85% |
| 9 | 1h | 1.2 | 10 | 2h | 84% |
Isolated yields on 0.5 mmol scale.
Protected from light (Al foil over flask).
CH2Cl2 as solvent.
Added HOAc (≥ 2 eq)
