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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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Updated: Jun 13, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

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

Published on: March 6, 2019

オキシマチイラン (Oxathiirane) とは

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
まとめ
この要約は機械生成です。

研究者は,写真化学を用いて硫黄素から難解な親オキサチラン分子を合成しました. この画期的な発見は,硫黄の転移反応と硫黄を含む化合物の安定性に関する洞察を提供します.

さらに関連する動画

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

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

関連する実験動画

Last Updated: Jun 13, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

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

Published on: March 6, 2019

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

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

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

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • フォトケミストリー フォトケミストリー
  • コンピューティング・ケミストリー

背景:

  • 硫黄を含むヘテロサイクルは,様々な化学反応において極めて重要です.
  • オクサチランの親分子は,長い間探されてきたが,特徴づけられていない分子である.
  • そのような化合物の安定性と反応性を理解することは,硫黄化学の進歩の鍵です.

研究 の 目的:

  • 親子オキサチランの最初の合成を達成するために.
  • オキサチランの構造と安定性を特徴付けるために.
  • オキサチランの安定性を,その酸素アナログであるダイオキシランと比較する.

主な方法:

  • 光 (lambda = 313 +/- 10 nm) を使用してスルフィンの光化学的再配置.
  • 凍結温度 (11 K) のアルゴン (Ar) マトリックスでの分離と特徴付け.
  • 振動周波数分析のためのハイレベル計算化学 (CCSD(T) /cc-pVTZ).

主要な成果:

  • オキサチランの成分の準備と特徴づけが成功しました.
  • 実験的な振動周波数と計算された振動周波数の間の優れた一致は,構造を確認しました.
  • オキサチランは,スルフィンよりも約10 kcal mol ((-1) ほど安定性が低い.

結論:

  • オキサチランの合成は,硫黄化学のための新しい構成要素を提供します.
  • スルフィンと比較して相対的な不安定性は,電子効果に起因する.
  • オキサチランは,硫黄移転反応における重要な中間物質である可能性が高い.