Table 1. Effect of Temperature, Oxygen, and Scale.
entry | T (°C) | t (h) | yield of 2a | yield of 1a | exo:endo ratioa |
---|---|---|---|---|---|
1 | 22 | 16 | 57 | <5 | 5.5:1 |
2 | 5 | 8 | 53 | <5 | 5.1:1 |
3b | 22 | 16 | 24 | 42 | 4.3:1 |
4c | 5 | 12.5 | 6 | 80 | 3.3:1 |
5d | 5 | 12.5 | 22 | 44 | 2.7:1 |
6e | 5 | 12.5 | 33 | 29 | 4.6:1 |
7f | 5 | 13 | 40 | 26 | 3.5:1 |
8g | 5 | 13 | 40 | 23 | 3.3:1 |
Calculated by UPLC (PDA).
Reaction performed at a 0.50 mmol scale.
Reaction deoxygenated via freeze–pump–thaw.
Reaction performed under a balloon of oxygen.
Reaction performed under a balloon of air.
Reaction sparged continuously with air (0.25 mmol scale).
Reaction sparged continuously with air (0.50 mmol scale).