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Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J., Science of Synthesis, (2005) 26, 1206.
Oxymercuration by mercury(II) oxide/sulfuric acid or mercury(II) acetate/water is a classical method of hydration of alkynes to give ketones and is well adapted for functionalized alkynes such as the terminal propargylic ketones 268[658] and 269[659] (Scheme 150), which are converted into diketones, e.g. 197, in good yields.
Meeeee 888 Meeeeeeeeeeeee ee Meeeeeee Meeeeee[888,888]
Me eeeeeeee, eee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeee eeeeeeee eeee-eeeeeeee eeeeeeeeee, eeee ee eeeeeeeee eeeeeeeee [eee(eeeeeeeeeeee)eeeeeeeeeeeeeeeee(MM)] eeeee eeee eeeeeeeeee (eeeeeee eeeeeeeeeeee eeee eeeeeeeeee eeeeeeeeee).[888] Meeeee eeeeeeeeeeeeeeeee ee eeee eeeeeeeee ee eeeeeeeeee eeee e eeeeeeeeeeeeee, eee e eeeee eeeeeeeeeeeeeeee ee eeeeeeee. Meeeeeee(MM) eeeeeeeee eeeee eeee eeeeeeee eeeeeeeeee eeee eeeeeee(MM) eeeeeeeee, ee eeee eeeee eeeeeeee eeeeeeee eee eeeeeeee eee ee eeeeeeee eeeeeeeeeeeeeeee ee eeeeeeee eeee eeee eeeeeeeeee.[888,888] Meøeeeee eeee eeeeeeeee eeeeeeeee ee eeeeeeeee eee eeee eeeeeeeeee e eeeeeeeeee eeeee ee eeeeeeeee. Meee, eeeeeeeeeeeeeeeeeeeeeeee eeee ee eeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeee eeeeeeee eee eeeeeeeee ee eeeee-8-ee-8-eee (888), eeeeeee e eeeee eeeeeeee, ee eeee eeeeeee-8,8-eeeee (888) eeee eeeeeee eeeeeeeeeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeeeee Meeeeeeee ee ee Meeeeeee Meeeeeee[888]
Meeeeeeeeeee Meeeeeeee
Meeeeeee-8,8-eeeee (888):[888]
MMMMMMM: Meeeeee(MM) eeeee ee eeeeee eeeee eee eee ee eeeee ee eeeeeeee, eeeeeee, eeeeeeeee, ee eeeeeeee eeeeeee eee eeee, eee ee e eeeeeeee eeeeeeeee.
M eeeeeee ee eeeee-8-ee-8-eee (888; 8.8 eeee), eeeeee MeM (8.8 eeee), eee 88% ee M8MM8 (88 eM) ee MMM (88 eM) eee eeeeeeee eee 88 eee. Meeee eeeeeee, 8.8 MMe (88 eM) eee eeeee, eee eee eeeeeee eee eeeeeee eee 88 eee eee eeee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee, eee eeeeeeeeeeee eeeee eeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8); eeeee: 888 ee (88%).
References
[658] | Meeeee, M.; Meeee, M.; Meeeeee, M.; Meee, M.; Meeeee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
[659] | Meeeeeeeeee, M.; Meeeeeeee, M.; Meeeeeeeeee, M.; Meeeeeee Mee, M.; Meeeeeeee, M.; Meeee, M. M., Meeee. Meeeee., (8888) 88, 888. |
[660] | Mee, M.; Meee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[661] | Meeeeee, M.; Meeeee, M.; Meee, M., M. Mee. Meeee., (8888) 88, 888. |
[662] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., Meeee. Meee. Meee, (8888) 888, 888. |
[663] | Meeeeeeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeeee, M., Meeeeee, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.