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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Heterogeneous Catalysis

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...

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Methanol Conversion into Dimethyl Ether on the Anatase TiO2(001) Surface.

Feng Xiong¹, Yan-Yan Yu², Zongfang Wu¹

¹Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Materials for Energy Conversion, and Department of Chemical Physics, University of Science and Technology of China, Jinzhai Road 96, Hefei 230026 (P. R. China).

Angewandte Chemie (International Ed. in English)

|November 24, 2015

Summary

This study reveals that methanol reacts to form dimethyl ether on specific titanium dioxide (TiO2) surfaces. This finding highlights TiO2

Keywords:

density functional calculations ethers heterogeneous catalysis surface chemistry titanium

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Area of Science:

Surface chemistry
Catalysis
Materials science

Background:

Methanol reactions on TiO2 are crucial for C1 chemistry and photocatalysis.
Understanding these reactions aids in developing efficient catalytic processes.

Purpose of the Study:

To investigate methanol adsorption and reaction pathways on the anatase TiO2(001)-(1×4) surface.
To identify the mechanism of methanol-to-dimethyl ether (DME) conversion.
To compare the reactivity of this specific TiO2 facet with others.

Main Methods:

Combined experimental and theoretical calculation approaches.
Surface science techniques to study adsorption and reaction intermediates.
Density Functional Theory (DFT) calculations for reaction mechanisms.

Main Results:

The methanol-to-dimethyl ether (DME) reaction proceeds via dehydration coupling of methoxy species.
This reaction occurs specifically at fourfold-coordinated Ti(4+) sites (Ti(4c)).
The anatase TiO2(001)-(1×4) facet exhibits higher reactivity than previously studied TiO2 facets.
Co-adsorbed water has minimal impact on methanol surface chemistry.

Conclusions:

The study elucidates the fundamental surface chemistry of methanol on TiO2.
TiO2 surfaces rich in Ti(4c) sites are identified as promising catalysts for selective methanol-to-DME conversion.
This research advances the understanding of C1 chemistry and photocatalysis.