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Please login to access the full content or check if you have access via26.9.1.1.22 Method 22: Isomerization of Propargylic Alcohols
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Marsden, S. P., Science of Synthesis, (2005) 26, 1103.
Propargylic alcohols can be rearranged to enones to give one of two regiochemical outcomes.[261] The Rupe rearrangement is believed to proceed through elimination of water followed by regioselective hydration of the alkyne, giving the rearranged enone 340 (Scheme 58). The Meyer–Schuster rearrangement proceeds by interception of a propargylic cation, leading to transposition of the oxygen and hence enones of the type 341.
Meeeee 88 Meeeeeeeeeeee Meeeeeee ee Meeeeeeeeeeeee ee Meeeeeeeeee Meeeeeee
Mee Meee eeeeeeeeeeeee ee eeeeeeee ee eeeeee eeeee,[888] eee eee eee ee eeeeeeeee eeeee eeeee (Meeeee-M eeeee) ee eeeeeeee ee eeee eeeeeeee eeeeeee, eeeeeeeeeee ee eee eeee-eeeeeeee eeeeeeeeee ee eeeeeeeeeee eeeeeee 888 eeee eeeee 888 (Meeeee 88).[888]
Meeeee 88 Meee eee Meeee–Meeeeeee Meeeeeeeeeeeee[888,888]
Mee Meeee–Meeeeeee eeeeeeeeeeeee ee eeee eeeeeeee ee eeeeee eeee,[888] eee eeeeee eee eeee eeeeeeeee eeeeeeeeee eee eeeeeeee eeeee eeee eee eee ee eeeeeeeee[888] ee eeeeee eeeee eee eeeee eeeeeeeee.[888] Mee eeee eeeeeeeee eeeeeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeee(MMM) eee 8-eeeeeeeeeeeeeee eeee eee eeee eeeee ee ee eeeeeeeeeeee eeeeeeeee, ee ee eee eeeeeeeeee ee 888 eeee 888.[888] Mee eeeeeeeeeeee ee eee eeeeeeee ee eee eee eeeee ee eeeeee eeeeeeeeeeeeeee eeee ee eeeeeeeee eeeeeeeeeee eee eeee eeee eeeeeeee.[888]
Meeeeeeeeeeeeee eeee ee 888 eeee eeee eeeeeeeeeee ee eee eeeeeeeeeeeeeeeeeeee(8)-eeeeeeee eeeeeeeeeeeee ee eeeeeeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeeeee, e.e. 888 (Meeeee 88). Mee eeeeeeee ee eeeeeeee ee eee eeeeeeee ee eeeeeeeeee(MMM) eeeeeee.[888]
Meeeee 88 Meeeeeeeeeeee ee e Meeeeeeeeee Meeeeeeeeee Meeeeee[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
M eeeeeee ee 8-eeeeeeeeeeeeeeeeeee (888; 8.88 e, 88 eeee) eee Meeeee-M (8 e) ee MMe8 (88 eM) (MMMMMMM: eeeee) eee eeeeeeee eee 88 e eeeee eeeee eeee MMM eeeeeeee eeeeee eee eeeeeeee ee ee eeeeeeee. Mee eeeee eeeee-eeeee eeee eee eeeeeeee eee eee eeeeeee eeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 8.88 e (88%); ee 888–888°M/88.8 Meee.
References
| [261] | Meeeeeeeeee, M.; Meeeeeeee, M. M., Meee. Mee., (8888) 88, 888. |
| [262] | Meee, M. M.; Meee, M. M., Meeeeeeee, (8888), 888. |
| [263] | Meeeeee, M.; Meeeeee, M. M.; Meeeeee, M. M., Meee. Meee. Meee, (8888) 88, 8888. |
| [264] | Meeeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeee, M.; Meeeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
| [265] | Meeeeeee, M.; Meeeee, M.; Meeeeee, M., Meee. Meee., (8888), 8888. |
| [266] | Mee Meeeee, M.; Meeeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [267] | Meeeeee, M.; Meeeee, M., Meee. Meee., (8888), 888. |
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