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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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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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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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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.
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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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Phosphido-borane-supported stannates.

Keith Izod1, Atheer M Madlool1, Alex Craig1

  • 1Main Group Chemistry Laboratories, School of Chemistry, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK. keith.izod@ncl.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|January 4, 2023
PubMed
Summary
This summary is machine-generated.

Tin(II) chloride reacts with alkali metal phosphido-boranes to form novel tris(phosphido-borane)stannate complexes. These complexes exhibit diverse structures, including monomers, dimers, and polymers, influenced by alkali metal and ligand substituents.

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Coordination Chemistry

Background:

  • Alkali metal phosphido-borane complexes are versatile reagents in main group chemistry.
  • Tin(II) chloride serves as a precursor for various organotin compounds.

Purpose of the Study:

  • To synthesize and characterize novel tris(phosphido-borane)stannate complexes.
  • To investigate the structural diversity of these complexes based on varying alkali metals and phosphido-borane ligands.
  • To explore the reactivity of tin(II) chloride with different phosphido-borane complexes.

Main Methods:

  • Reaction of tin(II) chloride with alkali metal phosphido-borane complexes.
  • X-ray crystallography for structural determination of the stannate complexes.
  • Multinuclear NMR spectroscopy to analyze reaction products.

Main Results:

  • Synthesis of tris(phosphido-borane)stannate complexes with trigonal pyramidal tin centers.
  • Structural characterization revealing monomers, dimers, and polymers based on alkali metal and R groups.
  • Observation of a different product, a known hydride, when using tert-butyldi-phosphido-borane complexes.

Conclusions:

  • The reaction of SnCl2 with phosphido-borane complexes offers a route to diverse stannate structures.
  • The coordination modes of phosphido-borane ligands and alkali metal interactions dictate the final supramolecular assembly.
  • Steric bulk of phosphido-borane ligands can influence the reaction outcome, leading to alternative products.