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Related Concept Videos

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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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.
8.8K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.5K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Systematic Study on the Catalytic Arsa-Wittig Reaction.

Ryoto Inaba1, Ikuo Kawashima1, Toshiki Fujii1

  • 1Faculty of Molecular Chemistry and Engineering, Graduate School of, Science and Technology, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto, 6068585, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 15, 2020
PubMed
Summary

1-phenylarsolane catalyzes efficient arsa-Wittig reactions, converting aldehydes to olefins with high yields and excellent E stereoselectivity. Density functional theory calculations provided insights into the reaction

Keywords:
E/Z selectivityarseniccatalytic arsa-Wittig reactiondensity functional calculationsiron-free

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • The arsa-Wittig reaction is a valuable synthetic tool for olefin synthesis.
  • Development of efficient and stereoselective catalytic methods is crucial for organic synthesis.

Purpose of the Study:

  • To develop an efficient catalytic arsa-Wittig reaction using 1-phenylarsolane.
  • To investigate the stereoselectivity of the developed catalytic system.
  • To elucidate the reaction mechanism using computational methods.

Main Methods:

  • Catalytic arsa-Wittig reactions utilizing 1-phenylarsolane as the catalyst.
  • Substrate scope exploration with various aldehydes.
  • Density functional theory (DFT) calculations to study reaction pathways and selectivity.

Main Results:

  • 1-phenylarsolane effectively catalyzed the arsa-Wittig reaction.
  • A wide range of aldehydes were converted to olefins in high yields.
  • Moderate to excellent E stereoselectivity was achieved.

Conclusions:

  • 1-phenylarsolane is an efficient catalyst for the arsa-Wittig reaction.
  • The catalytic system offers high yields and good stereoselectivity for olefin synthesis.
  • DFT calculations provide mechanistic insights into the observed E/Z selectivity.