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Merino, P., Science of Synthesis, (2007) 29, 776.
The reaction of 1,2,4-trioxolanes with methanol in the presence of chlorosulfonic acid gives good yields of carbonyl compounds, formed via the corresponding α-methoxy hydroperoxides.[353] The furan endoperoxides 287 afford the Δ2-butenolides 288 after thermal rearrangement at 35°C in basic solvents such as acetone, methanol, tetrahydrofuran, or dimethylformamide (Scheme 124).[302] On the other hand, the epoxides 289 and 290 are obtained in apolar solvents. The formation of the butenolide 288 is achieved in better yields if the reaction is carried out at a lower temperature (18–22°C) and in acetone as solvent.[354] It can be demonstrated by NMR spectroscopy that the reaction takes place through the rearrangement of 287 into the dioxetane 291, which leads to dimeric peroxides as immediate precursors of 5-(hydroperoxy)butenolides that afford the butenolide 288 after hydrolytic workup.[355]
Meeeee 888 Meeeeee Meeeeeeeeeeee ee Meeee Meeeeeeeeeeee[888]
Meeeeeee eeeeeeeeeee eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee ee eee eeeeee ee eeeeeee-eeeee eeeeeeeeeeeeeeeeee ee 88°M eeee 8 eeee.[888] M eeeeeee eeeeeeeeeeeeee ee eeeeeeee eeee eeeeee eeeeee, eeeee eeeeeeee eee 8,8,8-eeeeeeeeee 888 eeee eee eeeeeeeeee 888 (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeeeeeeee-8,88-eeeeeeeeeeeeee[888]
Meeeeeeee ee eeeeeeee ee eeee ee ee eeeeeeeee eeeeeee eee eee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeee, eeeeeeeee eeeeeeee. Mee eeeeeeeeeee 888 eee 888 eeeeee eee eeeeeeee eeeeeeeeeee 888 eee 888, eeeeeeeeeeee, ee eeee eeeeeeee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeeeeee Meeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeee-8,88-eeeeeeeeeeeeee (888):[888]
M eeee ee 8,8,8-eeeeeeeeee 888 (8 e, 8 eeee) eee MeM (8 e, 88 eeee) ee MeMM (88 eM) eee eeeeeee ee ee eee 8 e. Meee, eee. Me8M8M8 eeee eee eeeee ee eeeeee eee eeeeee M8 , eee eee eeeeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeee eeee MeMMM8 eeee, eeeee (Me8MM8), eee eeeeeeeeeeee; eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MM8Me8); eeeee: 8.8 e (88%).
References
| [302] | Meeeeeee, M. M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [353] | Meeee, M.; Meeeee, M.; Meeeeeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [354] | Meeeeeee, M. M.; Meeee, M. M., Meeeeeeee, (8888), 8888. |
| [355] | Meeee, M. M.; Meeeeeee, M. M.; Meeeeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [356] | Meeeeeeee, M. M.; Meeeee, M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [357] | Meeeeee, M.; Meeeeeeeee, M.; Meee, M.; Meeeeeee, M., Meee. Meee. Meee, (8888) 88, 8. |
| [358] | Mee, M.; Meeeeeee, M. M.; Meeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
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