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相关概念视频

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.0K
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.
9.0K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.4K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.4K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.0K
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.
19.0K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.4K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.4K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.5K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.5K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K

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相关实验视频

Updated: Sep 19, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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开发可电子调节的N-异环酸.

I J Huerfano1, Evgueni Gorobets1, Wen Zhou1

  • 1Department of Chemistry, University of Calgary, Calgary, AB T2N 1N4, Canada. jeffrey.vanhumbec1@ucalgary.ca.

Chemical communications (Cambridge, England)
|June 18, 2025
PubMed
概括

研究人员用N-异环替代剂合成了新型的质子酸盐,为多功能化学应用提供了可调的易斯基本性和布伦斯特-劳里酸性.

科学领域:

  • 有机金属化学 有机金属化学
  • 超分子化学 超分子化学
  • 酸化学 酸化学是指酸与酸之间的关系.

背景情况:

  • 酸盐化合物在化学合成和催化中具有多功能.
  • N-异环烯具有独特的电子和硬质性质.
  • 可调的易斯度和布伦斯特德 - 劳里酸度对于试剂设计至关重要.

研究的目的:

  • 合成和表征新型酸盐,其中包括N-异环替代物.
  • 为了研究这些新型酸盐的可调节电子和氧化还原特性.
  • 探索它们作为布伦斯特德 - 劳里酸及其盐衍生物的潜力.

主要方法:

  • 合成N-异环基替代酸盐.
  • 使用光谱技术 (例如NMR) 进行表征.
  • 通过 pKa 括号和动力学研究评估 Brønsted-Lowry 酸度.

主要成果:

  • 成功合成了新型质子化酸盐与N-异环替代剂.
  • 通过原子的质子化证明了可调的易斯基本性.
  • 量化布伦斯特德 - 劳里酸度和质子运动可访问性.

结论:

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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  • N-异环酸盐为酸化学提供了一个可调节的平台.
  • 这些化合物表现出与甲烯类似物具有可比性质,并具有额外的益处.
  • 合成盐在催化和材料科学中具有未来各种应用的潜力.