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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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The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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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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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.
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An Isolable Bis(Silanone-Borane) Adduct.

Marcel-Philip Luecke1, Elron Pens1, Shenglai Yao1

  • 1Department of Chemistry: Metalorganics and Inorganic Materials, Technische Universität Berlin, Strasse des 17. Juni 115, Sekr. C2, 10623, Berlin, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 5, 2020
PubMed
Summary

This study shows a new way to activate carbon dioxide (CO2) using a ferrocene-based compound. The reaction forms a borane-stabilized bis(silanone) by oxygenating silicon centers, releasing carbon monoxide (CO).

Keywords:
FLP-chemistrysilanonessilylenesmall-molecule activation

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Area of Science:

  • Organometallic Chemistry
  • Silicon Chemistry
  • Boron Chemistry

Background:

  • Ferrocene derivatives are versatile building blocks in synthesis.
  • Boranes act as Lewis acids, interacting with electron-rich species.
  • Carbon dioxide activation remains a key challenge in sustainable chemistry.

Purpose of the Study:

  • To synthesize and characterize novel bis(silylene-borane) Lewis adducts.
  • To investigate the reactivity of these adducts in carbon dioxide activation.
  • To explore the formation of borane-stabilized silanones.

Main Methods:

  • Reaction of bis(silylenyl)-substituted ferrocene with BPh3.
  • Carbon dioxide activation using the Lewis adduct.
  • Characterization of new compounds via single-crystal X-ray diffraction.

Main Results:

  • Formation of bis(silylene-borane) Lewis adduct 2.
  • Activation of CO2 to yield borane-stabilized bis(silanone) 3 with CO release.
  • Synthesis of 1,3,2,4-cyclodisiloxane and Me3P-BPh3 adduct.

Conclusions:

  • The bis(silylene-borane) adduct effectively activates CO2.
  • This provides a novel route to borane-stabilized silanones.
  • The study expands the scope of organosilicon and organoboron chemistry.