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Related Concept Videos

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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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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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.
17.3K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

20.4K
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:
20.4K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.7K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Updated: Dec 1, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Tetrel and pnictogen functionalised propargylidynes.

Richard A Manzano1, Anthony F Hill, Rosemary L Georgelin

  • 1Research School of Chemistry, Australian National University, Canberra, Australian Capital Territory ACT 2601, Australia. a.hill@anu.edu.au.

Chemical Communications (Cambridge, England)
|November 6, 2020
PubMed
Summary

New tungsten complexes enable the installation of main group elements, such as silicon and tin, onto propargylidyne termini. These anhydrous reagents offer versatile synthetic pathways for organometallic chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • Tungsten complexes with propargylidyne ligands are valuable synthetic intermediates.
  • Developing efficient methods for functionalizing these ligands is crucial for expanding their utility.

Purpose of the Study:

  • To synthesize novel tungsten-based reagents for installing main group elements.
  • To explore new reaction pathways for functionalizing propargylidyne termini.

Main Methods:

  • Reaction of a tungsten-alkynylsilane complex with silver nitrate.
  • Deprotonation of a mercury-bis(alkynyl) complex with n-butyllithium.

Main Results:

  • Formation of a silver-containing tungsten complex {[W([triple bond, length as m-dash]CC[triple bond, length as m-dash]CAg)-(CO)2(Tp*)][AgNO3]}n.
  • Synthesis of a lithium-tethered tungsten complex [W([triple bond, length as m-dash]CC[triple bond, length as m-dash]CLi)(CO)2(Tp*)].
  • Demonstration of these reagents' ability to install main group elements (Si, Sn, Pb, P, As) as propargylidyne termini.

Conclusions:

  • The developed anhydrous tungsten reagents provide a versatile platform for introducing main group elements.
  • These methods expand the synthetic accessibility of functionalized propargylidyne ligands in organometallic chemistry.