You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via31.5.1.3.4 Method 4: Rearrangement of Dienones
Please login to access the full content or check if you have access via
González-Bello, C.; Castedo, L., Science of Synthesis, (2007) 31, 324.
Highly substituted phenols can be readily obtained from cyclohexadienones by an acid-catalyzed, a base-catalyzed, or a photochemical dienone–phenol rearrangement. The driving force of the process is the formation of an aromatic product, which is usually obtained in good yields. A large variety of protic acids (e.g., HCl, H2SO4, AcOH, TsOH, or TFA) or Lewis acids (e.g., BF3•OEt2) can be used. For example, phenols 30 can be effectively obtained in a few minutes at room temperature from cyclohexadienones 29 by treatment with a Lewis acidic iron(III)-doped montmorillonite K 10 clay system (Scheme 9).[26]
Meeeee 8 Meeeeeeeeee ee Meeeeee ee Meee-Meeeeeeee Meeeeee–Meeeee Meeeeeeeeeeee[88]
Me eee eeeee eeee, eeeeee eeeeeeeeeee eeeeeee 88 eee ee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeee ee eeeeeeeee-8,8-eeee-8-eeee 88 (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeee ee Meeeeeeeeeeeeeee Meeeeee ee Meeeeeeeeeeee Meeeeee–Meeeee Meeeeeeeeeeee[88]
Meeeeee[8.8.8]eee-8-ee-8-eeee eee eeee eeee eeeeeeee eeeeeeeee ee eee eeeeeeeee ee eeeeeee ee eeeeeeeeeeeee. Mee eeeeeee, eeeeeee eeeeeee[8.8.8]eee-8-ee-8-eeee 88 eeee eeeeeeeee eeeeeeeee, ee eeee-eeeeeeee eeeeeeee eee eeeeee eeeeeeeeeee eeeeeee 88 (Meeeee 88).[88] Mee eeeeeeeeeeee eeeeeeeeee ee eeeeee 88 eeee eeeeeee 88 ee eeeeeeee ee eeeeeeeeeee eeee MM eeeee (888 ee).[88]
Meeeee 88 Meeeeeeee ee Meeeeeeeeee Meeeeee ee Meeeeeeeeeeee ee Meeeeee[8.8.8]eee-8-ee-8-eeee[88,88]
Meeeeeeeeeee Meeeeeeee
8,8,8-Meeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
M eeee ee eee eeeeeee 88 (888 ee) eee eeee(MMM)-eeeee eeeeeeeeeeeeeee M 88 eeee (8 e) ee eeeeee (88 eM) eee eeeeeee ee ee eee 88–88 eee. Mee eeeeeeee eeeeeee eee eeeeeeee, eee eee eeeeeee eee eeeeee eeee MM8Me8 (88 eM) eee MeMM (88 eM). Mee eeeeeeee eee eeeeeeee eeee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee; eeeee: 88–88%.
Meeeee 8-Meeeeee-8-eeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
M 8.88–8.88 M eeee ee eee eeeeee eeeee 88 ee eeeeeee (MMMMMMM: eeeeeeeeee) eee eeeeeeee ee eeeeeeee eeeee eeeeeee eee eeee eee 88 eee. Meee eeeeeee eee eeee eeeeeeeeee eeeeeee eeeeeee eeeee ee 888 ee. Mee eeeeeee eee eeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 88–88%.
References
| [26] | Meeeeee, M.; Meeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [27] | Mee, M.; Meeeeee, M. M., Mee. Meee., (8888) 8, 8888. |
| [28] | Meeeeeeee, M.; Meeeeeeeeeeee, M., Meeee. Meeeee., (8888) 88, 8888. |
| [29] | Meeeeeeee, M.; Meeeeeee, M.; Meeà, M.; Meeeee, M.; Meeeeàe, M. M.; Meeee, M., Mee. Meee., (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e8, 888.
Return to Top