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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

11.6K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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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.
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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.
17.4K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

20.5K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
20.5K
Cycloalkanes02:28

Cycloalkanes

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Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Synthetic Routes for Heteroatom-Containing Alkylated/Arylated Polycyclic Aromatic Hydrocarbons.

Qinqin Shi1, Xiaosong Shi2, Changfu Feng3

  • 1Center of Materials Science and Optoelectronics Engineering, College of Materials Science and Opto-Electronic Technology & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum Physic, University of Chinese Academy of Sciences, Beijing, 100049, P. R. China.

Angewandte Chemie (International Ed. in English)
|October 27, 2020
PubMed
Summary
This summary is machine-generated.

Researchers developed new synthetic routes for heteroatom-containing polycyclic aromatic hydrocarbons (H-PAHs). These novel H-PAHs, including H-rubicenes and angular-benzothiophenes, show promise for electronic applications.

Keywords:
cross-couplingcyclizationpolycyclic aromatic hydrocarbonsstructure elucidationsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Chemical Synthesis

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are crucial in organic electronics.
  • Developing novel heteroatom-containing PAHs (H-PAHs) expands material properties.
  • Efficient synthesis of substituted H-PAHs remains a challenge.

Purpose of the Study:

  • To demonstrate synthetic routes for alkyl and aryl-substituted H-PAHs.
  • To synthesize three specific H-PAHs: heteroatom-containing rubicenes (H-rubicenes), angular-benzothiophenes (ABTs), and indenothiophene (IDTs).
  • To comprehensively investigate the properties of ABTs and H-rubicenes.

Main Methods:

  • Two key synthetic steps: polysubstituted olefin formation and cyclization.
  • Characterization techniques including single-crystal X-ray diffraction and NMR spectroscopy.
  • Photophysical and electrochemical investigations using UV-vis absorption and cyclic voltammetry.
  • Charge transport properties evaluated by transient absorption and single-crystal organic field-effect transistor (OFET) measurements.

Main Results:

  • Successful synthesis of three distinct H-PAH scaffolds: H-rubicenes, ABTs, and IDTs.
  • Detailed structural and electronic characterization of ABTs and H-rubicenes.
  • Demonstration of their potential for electronic device applications through OFET measurements.

Conclusions:

  • Established efficient synthetic pathways for novel H-PAHs.
  • Provided in-depth understanding of the structure-property relationships in ABTs and H-rubicenes.
  • Highlighted the potential of these synthesized H-PAHs in advanced electronic materials.