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Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

2.6K
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
2.6K
Esters to Alcohols: Grignard Reaction01:08

Esters to Alcohols: Grignard Reaction

4.8K
The reaction of an ester with a Grignard reagent, followed by hydrolysis of the magnesium alkoxide salt in aqueous acid, yields a tertiary alcohol. In the case of formate esters, secondary alcohols are formed.
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
4.8K
Alcohols from Carbonyl Compounds: Grignard Reaction02:00

Alcohols from Carbonyl Compounds: Grignard Reaction

6.3K
Grignard reagents are one of the most commonly used reagents used to synthesize alcohols from carbonyl compounds. Grignard reagents are organomagnesium halides with a highly polar carbon–magnesium bond. Due to the partial ionic nature of the C–Mg bond, the carbon functions as a strong nucleophile and attacks electrophiles like carbonyl carbon.
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the...
6.3K
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

5.1K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
5.1K
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

5.3K
Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
5.3K
Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

563
In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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A Thermally Stable Magnesium Phosphaethynolate Grignard Complex.

Akachukwu D Obi1, Haleigh R Machost1, Diane A Dickie1

  • 1Department of Chemistry, University of Virginia, 409 McCormick Road, P.O. Box 400319, Charlottesville, Virginia 22904, United States.

Inorganic Chemistry
|August 4, 2021
PubMed
Summary
This summary is machine-generated.

Stable magnesium phosphaethynolate complexes were synthesized using N-heterocyclic carbenes (NHCs). These novel compounds activate dioxane and exhibit unique reactivity, expanding group 2 chemistry applications.

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Coordination Chemistry

Background:

  • The 2-phosphaethynolate (OCP) anion is versatile but underexplored in group 2 chemistry.
  • Challenges exist in isolating thermally stable OCP complexes.

Purpose of the Study:

  • To synthesize and characterize thermally stable magnesium phosphaethynolate complexes.
  • To investigate the reactivity of these novel complexes.

Main Methods:

  • Rational modification of coordination environments using 1,3-dialkyl-substituted N-heterocyclic carbenes (NHCs).
  • Isolation and characterization of magnesium phosphaethynolate complexes.
  • Investigation of reactivity with dioxane and solvent effects.

Main Results:

  • Thermally stable, structurally diverse, and hydrocarbon-soluble magnesium phosphaethynolate complexes were isolated, including a novel phosphaethynolate Grignard reagent.
  • Methylmagnesium and magnesium diphosphaethynolate complexes activated dioxane via H-atom abstraction.
  • An ether-free sodium phosphaethynolate complex was isolated, and reactivity was correlated with Mg2+ Lewis acidity.
  • Decomposition of a magnesium diphosphaethynolate complex yielded organophosphorus complexes, including a thermal decarbonylation product.

Conclusions:

  • N-heterocyclic carbenes enable the isolation of stable group 2 phosphaethynolate complexes.
  • These complexes exhibit unique reactivity, including dioxane activation.
  • The study expands the scope of phosphaethynolate chemistry in main group elements.