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Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

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Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
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Alcohols from Carbonyl Compounds: Reduction02:23

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

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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...
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Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

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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,...
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Protecting Groups for Aldehydes and Ketones: Introduction01:23

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Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Substrate-Modulated Reductive Graphene Functionalization.

Ricarda A Schäfer1, Konstantin Weber2, Maria Koleśnik-Gray3

  • 1Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.

Angewandte Chemie (International Ed. in English)
|October 27, 2016
PubMed
Summary
This summary is machine-generated.

Monolayer graphenides on SiO2 are more reactive than bilayers when functionalized with lambda-iodanes. Ditopic addend binding yields more stable products due to reduced lattice strain, highlighting substrate influence.

Keywords:
DFT calculationsRaman spectroscopyfunctionalizationgraphenetopicity

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Area of Science:

  • Materials Science
  • Surface Chemistry
  • Nanotechnology

Background:

  • Graphene derivatives, known as graphenides, offer tunable electronic properties.
  • Chemical functionalization is key to modifying graphene's reactivity and applications.
  • Understanding substrate effects is crucial for controlling surface reactions.

Purpose of the Study:

  • To investigate the covalent functionalization of mono- and bilayer graphenides using lambda-iodanes.
  • To compare the reactivity of monolayer versus bilayer graphenides on a SiO2 substrate.
  • To elucidate the role of addend binding and substrate interactions in the functionalization process.

Main Methods:

  • Mechanical exfoliation of graphene to produce mono- and bilayer graphenides.
  • Covalent functionalization using lambda-iodanes.
  • Statistical Raman spectroscopy and microscopy for reactivity assessment.
  • Density Functional Theory (DFT) calculations for mechanistic insights.

Main Results:

  • Monolayer graphenides on SiO2 substrates exhibit significantly higher reactivity compared to bilayers.
  • Ditopic addend binding results in more stable functionalized products than monotopic binding.
  • DFT calculations confirm that lower lattice strain in ditopic reactions contributes to product stability.
  • The chemical nature of the substrate (graphene vs. SiO2) critically influences the reaction outcomes.

Conclusions:

  • The reactivity of graphenide functionalization is highly dependent on layer number and substrate.
  • Ditopic binding strategies offer enhanced stability for functionalized graphenides.
  • This study provides fundamental insights into controlling graphenide chemistry for advanced material design.