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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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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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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

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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:
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1,2-Difunctionalization of Acetylene Enabled by Light.

Shiwei Lü1, Zipeng Wang1, Xiang Gao1

  • 1Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, 1510640, Guangzhou, China.

Angewandte Chemie (International Ed. in English)
|February 27, 2023
PubMed
Summary

This study introduces a novel method for directly converting acetylene into valuable chemicals. The new 1,2-difunctionalization reaction creates diverse C2-linked products with high selectivity, expanding synthetic possibilities.

Keywords:
1,2-DifunctionalizationAcetyleneOlefinsPhotochemistryRadical Chemistry

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Direct conversion of acetylene to commodity chemicals is desirable.
  • Existing methods primarily involve cross-coupling, hydro-functionalization, and polymerization.

Purpose of the Study:

  • To develop a new method for the direct 1,2-difunctionalization of acetylene.
  • To access diverse C2-linked 1,2-bis-heteroatom products.
  • To explore new synthetic routes from acetylene.

Main Methods:

  • Direct insertion of acetylene into bifunctional reagents.
  • Synthesis of diverse functionalized molecules and chiral ligands.
  • Mechanistic investigation using experimental and theoretical methods.

Main Results:

  • Achieved high regio- and stereoselectivity in acetylene difunctionalization.
  • Generated a variety of C2-linked 1,2-bis-heteroatom compounds.
  • Demonstrated the utility of products in synthesizing complex molecules and ligands.

Conclusions:

  • The developed method offers a novel pathway for acetylene utilization.
  • Provides access to valuable chemical building blocks with excellent control.
  • Expands the synthetic toolbox for organic chemists.