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Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

Crossed Aldol Reactions: Overview

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.

C–C Bond Formation: Aldol Condensation Overview

C–C Bond Formation: Aldol Condensation Overview

Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.

Base-Catalyzed Aldol Addition Reaction

Base-Catalyzed Aldol Addition Reaction

As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.

Acid-Catalyzed Aldol Addition Reaction

Acid-Catalyzed Aldol Addition Reaction

The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.

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Updated: Jan 11, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

CO-to-sugars conversion from one-pot two-step electro-organocatalytic process.

Ajeet Singh¹, David Martins-Bessa², Julien Bonin¹

¹Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, CNRS F-75005 Paris France julien.bonin@sorbonne-universite.fr marc.robert@sorbonne-universite.fr.

Chemical Science

|November 10, 2025

Summary

This summary is machine-generated.

Researchers developed a one-pot system to convert carbon monoxide (CO) into carbohydrates. This sustainable method uses electroreduction and organocatalysis to create valuable carbon chains from a simple C1 source.

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Last Updated: Jan 11, 2026

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Area of Science:

Sustainable Chemistry
Catalysis
Synthetic Biology

Background:

Converting single-carbon (C1) molecules into longer carbon chains (Cn) is crucial for sustainable chemical feedstocks.
Carbohydrates are complex molecules typically sourced from biomass, but de novo synthesis offers access to rare or unnatural variants.

Purpose of the Study:

To establish an integrated system for the de novo synthesis of carbohydrates from carbon monoxide (CO).
To develop a novel pathway for producing complex carbon chains using CO as a primary building block.

Main Methods:

A one-pot, two-step process was employed.
The system couples the electroreduction of CO to formaldehyde.
Organocatalytic oligomerization of formaldehyde yields C5-6 carbohydrates.

Main Results:

Successfully converted carbon monoxide into carbohydrates.
Achieved selective synthesis of C5-6 carbohydrates.
Demonstrated a fully integrated system for CO conversion.

Conclusions:

This work presents a novel pathway for utilizing CO as a feedstock for carbohydrate synthesis.
The integrated system offers a sustainable route to complex carbon chains.
This approach complements biomass-derived carbohydrate production.