DA reaction between cyclopentadiene 5 and various dienophiles.
| |||||
|---|---|---|---|---|---|
| Entrya | 5 | t (h) | Conv.b (%) | 10 yieldc (%) | endo : exod |
| 1 | 5a | 1 | 100 | 90 | 86 : 14 |
| 2e | 5a | 1 | — | — | — |
| 3 | 5b | 1 | 100 | Quant | 86 : 14 |
| 4e | 5b | 1 | 9 | — | — |
| 5e | 5b | 3 | 33 | 27 | 77 : 23 |
| 6 | 5c | 1 | 100 | Quant | 2 : 98 |
| 7 | 5d | 4 | 94 | 90 | 69 : 25 |
| 16 | 100 | 96 | 77 : 23 | ||
| 8 | 5e | 4 | 78 | 72 | 84 : 16 |
| 16 | 95 | 91 | 84 : 16 | ||
| 9 | 5f | 4 | 54 | 50 | 91 : 9 |
| 16 | 72 | 68 | 89 : 11 | ||
| 10 | 5g | 4 | 37 | 34 | 84 : 16 |
| 16 | 61 | 60 | 80 : 20 | ||
| 11 | 5h | 2 | Quant | 93 | >99 : 1 |
Reaction conditions: 9 (0.45 M), 5 (0.15 M), C6 and TrCl (0.039 M.) in 1.1 mL of water-saturated CDCl3, at rt.
Determined by 1H NMR analysis of the crude reaction mixture.
Isolated yield.
Determined by 1H NMR analysis of the crude reaction mixture according to literature data.21b,21d,27
The reaction was performed in the absence of C6 and TrCl.