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Hydroboration-Oxidation of Alkenes03:08

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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.
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To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:
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Resonance

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The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O bonds. 
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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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According to the theory of resonance, if two or more Lewis structures with the same arrangement of atoms can be written for a molecule, ion, or radical, the actual distribution of electrons is an average of that shown by the various Lewis structures.
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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...
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一个没有基的双坐标氧波.

Clement R P Millet1, Dominic R Willcox1, Gary S Nichol1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, United Kingdom.

Angewandte Chemie (International ed. in English)
|November 18, 2024
PubMed
概括
此摘要是机器生成的。

研究人员使用易斯酸,化 (AlCl3) 稳定了难以捉摸的氧 (R-BO),创造了一个独特的无,双坐标物种. 这一突破允许新的反应性,导致前所未有的异环.

关键词:
(Boron) 是一种的物质.氧氨酸 (Boroxine) 是一种碳烯化合物是一种碳烯化合物.氧波二氧化物是一种氧化物.多重结合多重结合

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科学领域:

  • 有机氧化物化学
  • 主要组化学主要组化学
  • 易斯的酸化学

背景情况:

  • 氧波 (R-BO) 是高度反应性和短暂的,通常三聚化成.
  • 现有的稳定方法涉及易斯基,从而产生具有改变性能的三坐标氧波.

研究的目的:

  • 为了合成和表征一个稳定的,无基的,双坐标的氧波.
  • 为了研究这种新型物种的结合和反应能力.

主要方法:

  • 用化 (AlCl3) 来分离一个双坐标的氧波作为易斯附加物.
  • 光谱表征,包括红外光谱检测,以确定 ν11BO 拉伸频率.
  • 计算分析以了解结合相互作用和电子性质.

主要成果:

  • 一种稳定,无基,双坐标的氧波,Mes*BO-AlCl3,被成功分离出来.
  • 一个强大的BO结合被证实通过a ν11BO延伸频率的1843厘米-1.1.
  • 计算研究揭示了一种高度极化的BO键,具有一些多重键特性,增强的易斯酸性,减少氧的基本性.

结论:

  • 与AlCl3的协调提供了一个新的途径来稳定没有易斯基的双坐标氧波.
  • Mes*BO-AlCl3 的独特电子特性使其具有新型的反应性.
  • 与酸 (PhN3) 的反应产生了前所未有的异环,开辟了化学的新途径.