Optimization of reaction conditionsa.
| |||||
|---|---|---|---|---|---|
| Entry | MgX2 (equiv.) | Temp [°C] | Conv.b [%] | Yieldb [%] | |
| 2a | 2a′ | ||||
| 1 | MgI2 (1.5) | 80 | 60 | 38 | 1 |
| 2 | MgI2 (2) | 80 | 62 | 40 | 2 |
| 3 | MgI2 (3) | 80 | 73 | 68 | 4 |
| 4 | MgI2 (3) | 100 | >99 | 93c | 6 |
| 5 | MgBr2 (3) | 100 | 99 | 93d | 5 |
| 6 | MgCl2 (3) | 100 | 94 | 89 | 4 |
All the reactions were conducted using 0.5 mmol of 1a in THF (2.5 mL).
GC yields with n-dodecane as an internal standard.
Isolated yield was 96% as a 94 : 6 trans/cis-mixture.
Isolated yield was 93% as a 94 : 6 trans/cis-mixture.