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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.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

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.

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

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Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

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Related Experiment Video

Updated: Jan 13, 2026

Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance

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Published on: September 5, 2018

Modulating the Coordinatively Unsaturated Mo Species through Oxide-Support Interaction for Enhanced Reverse Water-Gas

Hui Xin¹, Rongtan Li², Xuyuan Huang³

¹Analytical & Testing Center, Sichuan University, Chengdu, Sichuan 610064, China.

ACS Applied Materials & Interfaces

|January 7, 2026

Summary

This study demonstrates that oxide-support interactions tune coordinatively unsaturated molybdenum species, significantly enhancing reverse water-gas shift activity. MoO₃/m-ZrO₂ and MoO₃/a-TiO₂ catalysts show superior performance and stability.

Keywords:

MoO3 coordinatively unsaturated Mo species reaction mechanism reverse water–gas shift reaction strong oxide–support interaction surface and interface

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In situ FTIR Spectroscopy as a Tool for Investigation of Gas/Solid Interaction: Water-Enhanced CO2 Adsorption in UiO-66 Metal-Organic Framework

In situ FTIR Spectroscopy as a Tool for Investigation of Gas/Solid Interaction: Water-Enhanced CO2 Adsorption in UiO-66 Metal-Organic Framework

Published on: February 1, 2020

Area of Science:

Heterogeneous catalysis
Materials science
Surface chemistry

Background:

Coordinatively unsaturated metal species are crucial for oxide-based catalysts.
Tuning their surface density and stability is challenging due to uncontrolled reduction.

Purpose of the Study:

To investigate how host oxides influence coordinatively unsaturated Mo species formation and stability.
To correlate these species with reverse water-gas shift (RWGS) activity.

Main Methods:

Deposition of MoO₃ onto various oxide supports (m-ZrO₂, a-TiO₂, CeO₂, γ-Al₂O₃, SiO₂) using dry combustion.
Characterization of catalytic properties, focusing on RWGS reaction.

Main Results:

Strong oxide-support interactions on m-ZrO₂ and a-TiO₂ lowered reduction temperature, creating stable, high-surface-content coordinatively unsaturated MoO_2-x species.
MoO₃/m-ZrO₂ and MoO₃/a-TiO₂ exhibited significantly higher CO₂ reaction rates (21 and 14 times, respectively) compared to unsupported MoO₃.
These catalysts demonstrated excellent stability over 60 hours of reaction.

Conclusions:

Oxide-support interactions are key to controlling the formation and stability of active Mo species.
This strategy effectively enhances catalytic performance for the RWGS reaction.
The findings offer a method for optimizing metal oxide catalysts via interface engineering.