Ruthenium And Silver Reagents

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Presentation transcript:

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. Lec. 3

Silver Reagents

Silver Reagents Lec. 3

- mild oxidation of aldehyde to carboxylic acids Silver Oxide (AgO2) - mild oxidation of aldehyde to carboxylic acids Lec. 3

Prevost Reaction Ag(PhCO2)2, I2 Lec. 3

Other Metal Based Oxidations Osmium Tetroxide OsO4 review: Chem. Rev. 1980, 80, 187. -cis hydroxylation of olefins, old mechanism: Lec. 3

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.

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 Lec. 3

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