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Related Concept Videos

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

18.0K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Racemization and transesterification of alkyl hydrogeno-phenylphosphinates.

Guilhem Javierre1, Rémy Fortrie2, Marion Jean1

  • 1Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France.

Journal of Molecular Modeling
|April 29, 2017
PubMed
Summary
This summary is machine-generated.

Alkyl hydrogeno-phenylphosphinates react with alcohols via nucleophilic addition, forming intermediates that enable racemization and alcohol exchange. Theoretical and experimental data align on reaction mechanisms and energy barriers.

Keywords:
KineticModelingPhosphinatePseudorotationRacemizationTransesterification

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Area of Science:

  • Organophosphorus Chemistry
  • Reaction Mechanisms
  • Stereochemistry

Background:

  • Alkyl hydrogeno-phenylphosphinates are organophosphorus compounds with potential applications.
  • Understanding their reactivity with nucleophiles like alcohols is crucial for synthetic chemistry.

Purpose of the Study:

  • To investigate the reactivity of alkyl hydrogeno-phenylphosphinates with alcohols.
  • To elucidate the reaction mechanism, including intermediate formation and subsequent pathways.
  • To compare theoretical predictions with experimental observations for alcohol exchange reactions.

Main Methods:

  • Theoretical exploration using Density Functional Theory (DFT) calculations.
  • Experimental investigations of reactions between alkyl hydrogeno-phenylphosphinates and alcohols.
  • Analysis of reaction kinetics and thermodynamics, including Gibbs free energies.

Main Results:

  • Alcohol molecules act exclusively as nucleophiles, adding to form pentacoordinated intermediates.
  • These intermediates undergo competitive alcohol eliminations and Berry pseudorotations.
  • Racemization and alcohol exchange reactions are facilitated through these pathways.
  • DFT-predicted transition energies for ethanol exchange with ethyl hydrogeno-phenylphosphinate match experimental values.

Conclusions:

  • The study provides a comprehensive understanding of alkyl hydrogeno-phenylphosphinate reactivity with alcohols.
  • The proposed mechanism involving pentacoordinated intermediates explains observed racemization and alcohol exchange.
  • DFT calculations serve as a reliable tool for predicting reaction energetics in such systems.