Table 3.
Scope of the Aza-Prins Fluorocyclizationa
![]() | |||||
---|---|---|---|---|---|
| |||||
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.