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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

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.
Aldehydes and Ketones with Water: Hydrate Formation01:20

Aldehydes and Ketones with Water: Hydrate Formation

An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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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Related Experiment Video

Updated: Jun 5, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Cyclopropenium-activated cyclodehydration of diols.

Brendan D Kelly1, Tristan H Lambert

  • 1Department of Chemistry, Columbia University, New York, New York 10027, USA.

Organic Letters
|January 21, 2011
PubMed
Summary
This summary is machine-generated.

This study introduces cyclopropenium activation for dehydrative cyclization of diols into cyclic ethers. This efficient method rapidly produces tetrahydrofurans and tetrahydropyrans in high yields.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Cyclic ethers are important structural motifs in natural products and pharmaceuticals.
  • Efficient synthesis of tetrahydrofurans and tetrahydropyrans remains a key challenge in organic synthesis.

Purpose of the Study:

  • To develop a novel method for the dehydrative cyclization of diols to cyclic ethers.
  • To utilize cyclopropenium activation for efficient synthesis of five- and six-membered cyclic ethers.

Main Methods:

  • Dehydrative cyclization of 1,4- and 1,5-diols using 2,3-diphenylcyclopropene and methanesulfonic anhydride.
  • Employing cyclopropenium activation as a novel strategy for ether formation.

Main Results:

  • Rapid cyclization of various diol substrates to form tetrahydrofurans and tetrahydropyrans.
  • Achieved high yields for the synthesized cyclic ethers.
  • Demonstrated scalability with a gram-scale cyclization of a diterpene derivative.

Conclusions:

  • Cyclopropenium activation provides an effective and high-yielding route for synthesizing cyclic ethers from diols.
  • The developed method is versatile and applicable to complex molecules like diterpenes.