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Related Concept Videos

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.
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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.
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Structure and Nomenclature of Epoxides02:38

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 is more in the ring having a smaller number of...

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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Oxathiirane.

Peter R Schreiner1, Hans Peter Reisenauer, Jaroslaw Romanski

  • 1Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany. prs@org.chemie.uni-giessen.de

Journal of the American Chemical Society
|May 11, 2010
PubMed
Summary
This summary is machine-generated.

Researchers synthesized the elusive parent oxathiirane molecule from sulfine using photochemistry. This breakthrough provides insights into sulfur transfer reactions and the stability of sulfur-containing compounds.

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Published on: April 24, 2018

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Computational Chemistry

Background:

  • Sulfur-containing heterocycles are crucial in various chemical reactions.
  • The parent oxathiirane has been a long-sought but uncharacterized molecule.
  • Understanding the stability and reactivity of such compounds is key to advancing sulfur chemistry.

Purpose of the Study:

  • To achieve the first synthesis of the parent oxathiirane.
  • To characterize the structure and stability of oxathiirane.
  • To compare the stability of oxathiirane with its oxygen analog, dioxirane.

Main Methods:

  • Photochemical rearrangement of sulfine using light (lambda = 313 +/- 10 nm).
  • Isolation and characterization in an Argon (Ar) matrix at cryogenic temperatures (11 K).
  • High-level computational chemistry (CCSD(T)/cc-pVTZ) for vibrational frequency analysis.

Main Results:

  • Successful preparation and characterization of parent oxathiirane.
  • Excellent agreement between experimental and computed vibrational frequencies confirmed the structure.
  • Oxathiirane is less stable than sulfine by approximately 10 kcal mol(-1).

Conclusions:

  • The synthesis of oxathiirane provides a new building block for sulfur chemistry.
  • The relative instability compared to sulfine is attributed to electronic effects.
  • Oxathiiranes are likely important intermediates in sulfur transfer reactions.