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Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

Sharpless Epoxidation

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...

Base-Catalyzed Ring-Opening of Epoxides

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...

Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...

Accelerators

Accelerators

Accelerators in concrete serve as admixtures to speed up the hardening process, enabling the concrete to achieve early strength faster. Although accelerators do not necessarily impact the time it takes concrete to set, they reduce this time in practice. A common accelerator is calcium chloride, which is particularly useful for hastening early strength development in cold weather or for rapid repair jobs that require quick heat generation after mixing.
The effectiveness of calcium chloride can...

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Related Experiment Video

Updated: Feb 12, 2026

Capillary-based Centrifugal Microfluidic Device for Size-controllable Formation of Monodisperse Microdroplets

Capillary-based Centrifugal Microfluidic Device for Size-controllable Formation of Monodisperse Microdroplets

Published on: February 22, 2016

Microdroplets Accelerate Ring Opening of Epoxides.

Yin-Hung Lai¹, Shyam Sathyamoorthi¹, Ryan M Bain¹

¹Department of Chemistry, Stanford University, Stanford, CA, 94305, USA.

Journal of the American Society for Mass Spectrometry

|March 24, 2018

Summary

This summary is machine-generated.

Electrosprayed microdroplets dramatically accelerate epoxide ring-opening reactions by over 10⁵ times compared to bulk solution. This novel approach using morpholine offers significant potential for optimizing organic synthesis.

Keywords:

Electrospray ionization Epoxide ring opening Microdroplet Microparticle imaging velocimetry Reaction acceleration

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Area of Science:

Organic Chemistry
Physical Chemistry
Chemical Engineering

Background:

Nucleophilic epoxide opening is a fundamental organic reaction with broad applications.
Traditional bulk solution methods can be slow, requiring extended reaction times.
Microdroplet technology offers a novel environment for chemical transformations.

Purpose of the Study:

To investigate the effect of electrosprayed microdroplets on the rate of epoxide ring-opening reactions.
To explore the influence of various parameters on reaction kinetics within microdroplets.
To assess the potential of microdroplet technology for accelerating epoxide chemistry.

Main Methods:

Studied the reaction of limonene oxide and cis-stilbene oxide with morpholine.
Compared reaction rates in bulk solution versus electrosprayed microdroplets (1:1 water/methanol).
Analyzed product formation using nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS).
Investigated the impact of droplet size, solvent composition, gas pressure, and voltage.

Main Results:

A rate acceleration of approximately 10⁵ was observed in microdroplets compared to bulk solution.
Product yield reached 0.5% in 1 ms within microdroplets, while bulk reactions showed no detectable product after 90 min.
Reaction rates were significantly influenced by droplet size, solvent, gas pressure, and applied voltage.

Conclusions:

Electrosprayed microdroplets provide a highly effective environment for accelerating epoxide ring-opening reactions.
This acceleration is observed in multiple epoxide systems, suggesting broad applicability.
Microdroplet technology presents a promising avenue for enhancing epoxide ring-opening processes with potential for scale-up.