Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

6.5K
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...
6.5K
Preparation of Epoxides03:00

Preparation of Epoxides

7.7K
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...
7.7K
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

10.2K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
10.2K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.2K
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.
6.2K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.2K
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...
7.2K
Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

8.3K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
8.3K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Structural variations in (001)-oriented layered lead halide perovskites, templated by 1,2,4-triazolium.

Dalton transactions (Cambridge, England : 2003)·2020
Same author

Diradical Character of Neutral Heteroleptic Bis(1,2-dithiolene) Metal Complexes: Case Study of [Pd(Me<sub>2</sub>timdt)(mnt)] (Me<sub>2</sub>timdt = 1,3-Dimethyl-2,4,5-trithioxoimidazolidine; mnt<sup>2-</sup> = 1,2-Dicyano-1,2-ethylenedithiolate).

Inorganic chemistry·2020
Same author

Variable dimensionality in 'hollow' hybrid tin iodide perovskites.

Dalton transactions (Cambridge, England : 2003)·2020
Same author

Luminescent Dinuclear Copper(I) Complexes Bearing an Imidazolylpyrimidine Bridging Ligand.

Inorganic chemistry·2020
Same author

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.

Beilstein journal of organic chemistry·2020
Same author

Janus Face All-cis 1,2,4,5-tetrakis(trifluoromethyl)- and All-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)- Cyclohexanes.

Angewandte Chemie (International ed. in English)·2020
Same journal

3-Methyleneazetidine: a versatile building block for functional and post-modifiable polysulfonamides.

Chemical communications (Cambridge, England)·2026
Same journal

Synthesis of divalent galactosyl and fucosyl spiropyran derivatives for the targeted inhibition of bacterial biofilms.

Chemical communications (Cambridge, England)·2026
Same journal

Emergent cytotoxicity and mitochondrial alterations induced by a heterobimetallic Re(I)/Au(I) complex.

Chemical communications (Cambridge, England)·2026
Same journal

Cyanoacetylation of amines <i>via</i> a traceless cyanoacetyl radical: synthetic access to teriflunomide.

Chemical communications (Cambridge, England)·2026
Same journal

Loading layered double hydroxide nanoarray catalysts on a micro-curved substrate for kinetics-favorable water electrolysis reaction.

Chemical communications (Cambridge, England)·2026
Same journal

Bridging <i>in situ</i> measurements and practical conditions through gas-liquid management for CO/CO<sub>2</sub> reduction.

Chemical communications (Cambridge, England)·2026
See all related articles

Related Experiment Video

Updated: May 6, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.1K

1,4-oxazine.

R Alan Aitken1, Kati M Aitken, Philip G Carruthers

  • 1EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK. raa@st-and.ac.uk.

Chemical Communications (Cambridge, England)
|October 29, 2013
PubMed
Summary
This summary is machine-generated.

Researchers synthesized the fundamental 1,4-oxazine heterocyclic compound using flash vacuum pyrolysis (FVP). This marks the first spectroscopic characterization of a parent oxazine, revealing its exclusive existence as the 4H-isomer in solution.

More Related Videos

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

7.9K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

7.4K

Related Experiment Videos

Last Updated: May 6, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.1K
Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

7.9K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

7.4K

Area of Science:

  • Heterocyclic chemistry
  • Organic synthesis
  • Spectroscopy

Background:

  • 1,4-oxazine is a fundamental heterocyclic scaffold.
  • Characterization of parent heterocycles is crucial for understanding chemical properties.
  • Previous studies lacked spectroscopic data for the parent 1,4-oxazine.

Purpose of the Study:

  • To synthesize and characterize the parent 1,4-oxazine molecule.
  • To determine the isomeric form of 1,4-oxazine present in solution.
  • To investigate the structural parameters of a related precursor.

Main Methods:

  • Flash Vacuum Pyrolysis (FVP) for synthesis.
  • Spectroscopic techniques for characterization.
  • X-ray crystallography for precursor structure determination.

Main Results:

  • Successful generation and spectroscopic characterization of 1,4-oxazine.
  • Confirmation of the exclusive existence of the 4H-isomer in solution.
  • X-ray data revealed geometric deviations in the N-Boc precursor compared to theoretical predictions.

Conclusions:

  • The parent 1,4-oxazine has been synthesized and fully characterized.
  • The 4H-isomer is the dominant form in solution.
  • Experimental structural data provides valuable insights for theoretical modeling.