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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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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Oxidative Cleavage of Alkenes: Ozonolysis01:46

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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.
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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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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.
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Taming the parent oxoborane.

Gargi Kundu1,2, P R Amrutha1, K Vipin Raj2,3

  • 1Inorganic Chemistry and Catalysis Division, CSIR-National Chemical Laboratory Dr Homi Bhabha Road, Pashan Pune 411008 India ss.sen@ncl.res.in.

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|June 9, 2023
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Summary
This summary is machine-generated.

Researchers successfully isolated the parent oxoborane (HBO) for the first time using a novel boron-gallium compound. This breakthrough opens new avenues for understanding and utilizing multiply bound boron chemistry.

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Area of Science:

  • Inorganic Chemistry
  • Organoboron Chemistry
  • Main Group Chemistry

Background:

  • The isolation of the parent oxoborane (HBO) moiety has been a long-standing challenge in multiply bound boron chemistry.
  • Recent advancements have focused on stabilizing reactive boron species.

Purpose of the Study:

  • To achieve the laboratory isolation of the parent oxoborane (HBO).
  • To characterize the structure and bonding of the isolated oxoborane.

Main Methods:

  • Reaction of 6-SIDipp·BH3 with GaCl3 to form a boron-gallium compound.
  • Controlled addition of water to the boron-gallium intermediate.
  • X-ray crystallography and density functional theory (DFT) analyses.

Main Results:

  • Formation of an unusual boron-gallium 3c-2e compound.
  • Isolation of a rare acid-stabilized neutral parent oxoborane, LB(H)=O, featuring a terminal B=O double bond.
  • Characterization of a hydroxy oxoborane, LB(OH)=O, a monomeric form of metaboric acid, demonstrating the stability of the B=O moiety.

Conclusions:

  • The study reports the first successful laboratory isolation of the parent oxoborane (HBO).
  • The findings confirm the presence of a terminal B=O double bond and highlight the stability of this moiety.
  • This work provides a new platform for studying multiply bound boron compounds.