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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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Radical Oxidation of Allylic and Benzylic Alcohols

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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

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Dioxygen activation in soluble methane monooxygenase.

Christine E Tinberg¹, Stephen J Lippard

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, 02139, United States.

Accounts of Chemical Research

|March 12, 2011

Summary

This summary is machine-generated.

Methane oxidation to methanol is challenging industrially. Methane monooxygenase enzymes activate oxygen at a diiron active site, forming key intermediates like P*, H(peroxo), and Q, enabling efficient methane conversion.

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Area of Science:

Biochemistry and enzymology
Bioinorganic chemistry
Oxidation catalysis

Background:

Controlled oxidation of methane to methanol is crucial for alternative fuels but industrially challenging.
Methane monooxygenase enzymes (MMOs) efficiently catalyze this reaction under ambient conditions.
Understanding MMOs provides insights into industrial catalysis and bio-inspired synthetic methods.

Purpose of the Study:

To elucidate the initial steps of methane oxidation catalyzed by soluble methane monooxygenase (sMMO).
To characterize the mechanism of reductive oxygen activation at the diiron active site.
To provide benchmarks for dioxygen activation mechanisms in related enzymes.

Main Methods:

Spectroscopic characterization of reaction intermediates.
Studies at varying pH and using D2O to probe proton transfer mechanisms.
Analysis of the diiron active site's role in oxygen activation and methane oxidation.

Main Results:

Identified key intermediates: peroxodiiron(III) species P* and H(peroxo), and diiron(IV) species Q.
Demonstrated that proton transfer is essential for O-O bond cleavage and conversion of intermediates.
Established Q as the species directly responsible for methane oxidation to methanol.

Conclusions:

The reductive activation of O2 by sMMO involves a series of diiron intermediates.
Proton transfer plays a critical role in facilitating O-O bond cleavage and subsequent catalytic steps.
Further structural and mechanistic studies are needed to fully define the sMMO catalytic cycle.