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Related Concept Videos

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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
11.1K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

17.1K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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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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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.3K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.4K

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A direct, versatile route to functionalized trialkoxysilanes.

Béatrice Quiclet-Sire1, Yuuki Yanagisawa, Samir Z Zard

  • 1Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, F-91128 Palaiseau, France. zard@poly.polytechnique.fr.

Chemical Communications (Cambridge, England)
|January 22, 2014
PubMed
Summary
This summary is machine-generated.

Radical addition of dithiocarbonates to vinylsilanes creates functionalized silanes. Pre-adding dithiocarbonates to alkenes enhances the final product

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Area of Science:

  • Organosilicon Chemistry
  • Radical Reactions
  • Organic Synthesis

Background:

  • Trialkoxy vinylsilanes are versatile building blocks in organic synthesis.
  • Radical additions offer efficient pathways for C-C and C-heteroatom bond formation.

Purpose of the Study:

  • To investigate the peroxide-initiated radical addition of dithiocarbonates to trialkoxy vinylsilanes.
  • To explore methods for increasing the complexity of the resulting functionalized silanes.

Main Methods:

  • Peroxide initiation of radical reactions.
  • Addition of dithiocarbonates (xanthates) to trialkoxy vinylsilanes.
  • Sequential addition of dithiocarbonates to alkenes followed by vinylsilane reaction.

Main Results:

  • Successful synthesis of functionalized trialkoxysilanes via radical addition.
  • Demonstration that pre-addition to alkenes yields more complex products.
  • Characterization of the synthesized organosilicon compounds.

Conclusions:

  • Peroxide-initiated radical addition is an effective method for functionalizing trialkoxysilanes with dithiocarbonates.
  • Sequential addition strategies enable the construction of intricate molecular architectures.
  • This methodology expands the synthetic utility of vinylsilanes in organosilicon chemistry.