Table 2 Thermolysis of isoxazolin-5-ones 8 in the presence and absence of potassium ethoxide
From: N-heteroatom substitution effect in 3-aza-cope rearrangements
# | Compounds 8 | Conditions | Products Yielda(%) | |
|---|---|---|---|---|
Temp./Time | 9 | Others | ||
1 | 8a: R = H | 60°C / 30 m | 9a (75) | - |
2 | 8b: R = Me | 60°C / 10 m | 9b (85) | - |
3 | 8c: R’ = Me | 180°C / 7 h | 9c (95)b | - |
4 | 8d: R’ = Ph | 180°C / 5 h | 9d (97) | |
5 | 8e | 180°C / 5 h | - | 12 (80) |
6 | 8e | EtOKc,d / RT / 5 h | - | 13 (80) |
7 | 8d: R’ = Ph | EtOKc,d / RT / 10 m | - | 14 (25) 15 (45) |
8 | 8b: R = Me | EtOKc,e / RT / 5 d | 9b (55) | - |
EtOKc,d / RT / 10 m | 9b (30) | - | ||