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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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.
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Exceptions to the Octet Rule02:55

Exceptions to the Octet Rule

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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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4.0K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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预先组织的二极管作为高效的1或2电子陷.

Alexander Hübner1, Thomas Kaese1, Martin Diefenbach1

  • 1†Institut für Anorganische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, Germany.

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概括

研究人员从bis{9-borafluorenyl) 甲中合成了一种红色的dianion盐和一个深绿色的monoanion基. 这些研究揭示了monoanion基和dianion的直接B-B结合相互作用,通过光谱学和晶体学得到证实.

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科学领域:

  • 有机化学 有机化学
  • 超分子化学 超分子化学
  • 光谱学和结晶学研究.

背景情况:

  • 比斯9-博拉烯) 甲作为新型含化合物的前体.
  • 了解元素对元素的结合对于开发新材料和反应途径至关重要.

研究的目的:

  • 合成和表征 bis ((9-borafluorenyl) 甲的二和单基.
  • 研究这些减少物种中的-相互作用的性质.
  • 为了探索离子与质子的反应性.

主要方法:

  • 使用金属进行化学还原.
  • 相对比例反应. 相对比例反应.
  • 电子偏磁共振 (EPR) 光谱学.电子偏磁共振 (EPR) 光谱学.
  • 一个X射线晶体学.
  • 核磁共振 (NMR) 光谱学.核磁共振 (NMR) 光谱学.
  • 量子化学计算. 量子化学计算.

主要成果:

  • 合成红色迪亚尼盐Li2[1] 和深绿色单基Li[1].
  • EPR光谱学证实了和质子的超细合,表明未配对的电子定位.
  • 射线晶体学揭示了随着越来越大的缩小而减少的B···B距离 (2.534(2) Å到1.906(3) Å).
  • 2的质子化[1]产生了一种周期性水化物,具有B-H-B两电子三中心键.
  • 计算分析表明,在减少的物种中,局部B-B相互作用.

结论:

  • 直接的B-B单电子和双电子结合相互作用分别建立在单离子基和二离子中.
  • 原子表现出核友性质,使B-B键的质子化等反应成为可能.
  • 这项研究提供了关于减少的有机系统中的结合的重要见解.