Table 3.
Scope of the Aza-Prins Fluorocyclizationa
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|---|---|---|---|---|---|
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| entry | R | time (h) | 5 | yield (%) | cis-5/trans-5b |
| 1 | cyclohexyl– | 4 | 5a | 100 | 10:1 |
| 2 | n-C5H11– | 4 | 5b | 100 | 8.5:1 |
| 3 | Ph– | 24 | 5c | 96 | 2:1 |
| 4 | 4-Br-C6H4– | 24 | 5d | 90 | 2.5:1 |
| 5 | 4-NO2C6H4– | 24 | 5e | 42 | 2:1 |
| 6 | 4-MeOC6H4– | 48 | 5f | 0 | |
4 (0.2 mmol), 2 (0.2 mmol), and DMPU/HF (2.1 mmol of HF) in DCE (0.5 mL) was mixed in a polyethylene vial and then stirred at 55 °C.
Determined by 19F NMR.
Room temperature.
Determined by 19F NMR using PhCF3 as internal standard.