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Related Concept Videos

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Al+ Activates Acetone to Form Pinacolate.

Apakorn Phasuk1, Ricardo B Metz1

  • 1Department of Chemistry, University of Massachusetts Amherst, Amherst, Massachusetts 01003, United States.

The Journal of Physical Chemistry Letters
|July 3, 2023
PubMed
Summary
This summary is machine-generated.

Aluminum cations interact with acetone, forming complexes studied using vibrational spectroscopy. Pinacolate formation, a reductive C-C coupling, was observed in larger aluminum-acetone clusters.

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Area of Science:

  • Physical Chemistry
  • Inorganic Chemistry
  • Spectroscopy

Background:

  • Gas-phase interactions of metal cations with organic molecules are crucial for understanding chemical processes.
  • Aluminum cations (Al+) are model systems for studying metal-ligand bonding and reactivity.
  • Acetone is a common organic solvent with a reactive carbonyl group.

Purpose of the Study:

  • To investigate the structural and electronic properties of aluminum cation-acetone complexes in the gas phase.
  • To elucidate the interaction mechanism between Al+ and acetone molecules using vibrational spectroscopy.
  • To identify the formation of pinacolate structures in aluminum-acetone clusters.

Main Methods:

  • Photodissociation vibrational spectroscopy was employed to study Al+(acetone)n clusters (n=2-5).
  • Density Functional Theory (DFT) calculations were performed to predict and assign vibrational spectra.
  • Comparison of experimental and calculated spectra was used to determine complex structures.

Main Results:

  • Observed red shift in the C=O stretch and blue shift in the CCC stretch of acetone upon complexation with Al+.
  • Shifts in vibrational frequencies decreased with increasing cluster size (n).
  • Experimental evidence for pinacolate formation (a C-C coupled product) was found for Al+(acetone)5, indicated by a peak at 1185 cm-1.

Conclusions:

  • The study reveals the structural evolution of Al+(acetone)n complexes with increasing ligand number.
  • DFT calculations successfully predicted the observed spectral changes and favored pinacolate structures for n>=3.
  • Experimental observation of pinacolate formation in Al+(acetone)5 confirms the proposed reductive coupling mechanism involving Al+ oxidation.