Transcript Ruthenium And Silver Reagents

Ruthenium And Silver
Reagents
Ruthenium And Silver Reagents
Ruthenium Tetroxide.
Fetizon Oxidation.
Silver Oxide.
Prevost Reaction.
Ruthenium Reagents
Ruthenium Tetroxide
- effective for the conversion of 1° alcohols to
RCO2H and 2° alcohols to ketones
- oxidizes multiple bonds and 1,2-diols.
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Silver Reagents
Silver Reagents
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Silver Oxide (AgO2)
- mild oxidation of aldehyde to
carboxylic acids
Lec. 3
Prevost Reaction Ag(PhCO2)2, I2
trans
cis
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Other Metal Based Oxidations
Osmium Tetroxide OsO4
review: Chem. Rev. 1980, 80, 187.
-cis hydroxylation of olefins, old mechanism:
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new mechanism:
reaction is accelerated in the presences
of an 3° amine Such as triethylamine or
pyridine
OsO4 bis-hydroxylation favors electon
rich C=C.
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Molybdenum Reagents
MoOPH [MoO5•pyridine (HMPA)]
JOC 1978, 43, 188.
- -hydroxylation of ketone, ester and lactone enolates.
Lec. 3
Palladium Reagents
Pd(0) catalyzed Dehydrogenation (oxidation) of
Allyl Carbonates (Tsuji Oxidation)
Tetrahedron 1986, 42, 4361
Allyl ester
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