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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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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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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

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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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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Phosphorus-Atom Transfer from Phosphaethynolate to an Alkylidyne.

Mehrafshan G Jafari1, Yerin Park2,3, Bimal Pudasaini3

  • 1Department of Chemistry, University of Pennsylvania, Philadelphia, PA, 19104, USA.

Angewandte Chemie (International Ed. in English)
|August 26, 2021
PubMed
Summary

This study introduces a novel vanadium complex formed via a unique P-atom transfer reaction. The research details the synthesis and electronic properties of this low-valent vanadium species, marking a first in organometallic chemistry.

Keywords:
alkylidynediketiminatephosphaalkynephosphorusvanadium

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • Vanadium complexes are crucial in catalysis and materials science.
  • Alkylidyne ligands offer unique reactivity in organometallic synthesis.
  • Phosphorus-containing ligands are vital for developing novel chemical transformations.

Purpose of the Study:

  • To synthesize and characterize novel mononuclear vanadium complexes.
  • To investigate the mechanism of a unique P-atom transfer reaction.
  • To explore the electronic ground state of low-valent vanadium species.

Main Methods:

  • Synthesis of vanadium neopentylidyne and isoelectronic ate-complexes.
  • Computational studies including Density Functional Theory (DFT) calculations.
  • Experimental characterization using UV/Vis and NMR spectroscopy, cyclic voltammetry, and X-ray absorption spectroscopy (XAS).

Main Results:

  • Successful preparation of a low-spin, mononuclear vanadium complex (2) and its isoelectronic ate-complex (4).
  • Elucidation of a [2+2]-cycloaddition followed by reductive decarbonylation mechanism for P-atom transfer.
  • Experimental and theoretical data confirm a low-valent vanadium ion in the synthesized complexes.

Conclusions:

  • This work presents the first metathesis reaction involving the P-atom of [PCO]− and an alkylidyne ligand.
  • The study establishes a new synthetic route to low-valent vanadium complexes with unique electronic properties.
  • The findings open avenues for further exploration of phosphorus-vanadium chemistry and its applications.