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Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.

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相关实验视频

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
13:09

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

通过Mo-催化环闭转化合成中环异环,三级和三级酒精的选择性合成.

Andrew F Kiely1, Jesper A Jernelius, Richard R Schrock

  • 1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.

Journal of the American Chemical Society
|March 21, 2002
PubMed
概括

催化不对称的环闭转化能有效地产生具有高反选择性的中环不和异环. 这些化合物作为有价值的三级酒精的前体.

科学领域:

  • 有机化学 有机化学
  • 催化剂是一种催化剂.
  • 合成化学 合成化学

背景情况:

  • 不对称的合成对于产生反反分子纯化合物至关重要.
  • 环闭转化是形成循环结构的强大工具.
  • 获得中环异环环的酶选择性仍然是一个合成的挑战.

研究的目的:

  • 开发一种高度选方法,用于合成中环不和异环环.
  • 探索催化非对称环闭转化论 (ARCM) 的实用性.
  • 为了证明获得的产品的合成多功能性.

主要方法:

  • 催化不对称环闭转化 (ARCM) 的阿基拉三烯.
  • 格拉姆级反应的优化.
  • 没有溶剂的反应条件.

主要成果:

  • 在中环不和 heterocycles 的形成中,高产量和优异的 enantioselectivity.
  • 成功地将ARCM反应扩大到克数量.
  • 实证了对对抗选择性西洛的功能化,使其成为三级酒精.

结论:

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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  • 催化ARCM是一种有效的策略,用于获取基丰富的中环异环环.
  • 开发的方法提供了一条实用且可扩展的途径,以获得有价值的合成中间体.
  • 由此产生的不和西洛干可提供难以合成的三级酒精.