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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.4K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

3.0K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
3.0K

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On-Surface Synthesis of BN-Substituted Heteroaromatic Networks.

Carlos Sánchez-Sánchez1, Sebastian Brüller2, Hermann Sachdev2,3

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ACS Nano
|August 18, 2015
PubMed
Summary

Researchers created novel boron and nitrogen (BN)-substituted heteroaromatic networks using surface-assisted polymerization. This method enables precise control over network structure and properties for advanced material applications.

Keywords:
bottom-upcovalent networkcyclodehydrogenationdensity functional theorygraphenehexagonal boron nitridescanning tunneling microscopy

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Surface Science

Background:

  • Bottom-up fabrication of complex organic networks is crucial for advanced materials.
  • Boron and nitrogen (BN)-substituted heteroaromatic networks offer unique electronic and structural properties.
  • Controlling network quality and achieving precise substitution patterns remain significant challenges.

Purpose of the Study:

  • To report the fabrication of BN-substituted heteroaromatic networks via surface-assisted polymerization and cyclodehydrogenation.
  • To investigate the influence of molecular flexibility on network formation and quality.
  • To demonstrate the potential for creating atomically precise substitution patterns in BNC heterostructures.

Main Methods:

  • Surface-assisted polymerization and cyclodehydrogenation of specifically designed BN-substituted precursor monomers.
  • Utilizing precursor monomers with varying degrees of internal cyclodehydrogenation.
  • Characterization using scanning tunneling microscopy (STM) and density functional theory (DFT) calculations.

Main Results:

  • Complete monomer cyclization and formation of covalently interlinked BN-substituted polyaromatic hydrocarbon networks on Ag(111).
  • Lower energy barrier for cyclodehydrogenation observed for a more conformationally rigid precursor monomer.
  • Higher degree of long-range order in the heteroaromatic network derived from the rigid precursor.

Conclusions:

  • Surface-assisted cyclodehydrogenation is an effective method for fabricating BN-substituted heteroaromatic networks.
  • Molecular rigidity of precursors significantly influences the order and quality of the resulting networks.
  • This approach provides a pathway for the precise engineering of BNC heterostructures.