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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 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

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Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
4.6K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
2.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
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,...
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The Azide-Wittig Reaction.

Kushik1, A Petrov1, D Ranieri2

  • 1Leibniz Institute for Catalysis (LIKAT), Albert-Einstein-Str. 29a, 18059, Rostock, Germany.

Angewandte Chemie (International Ed. in English)
|September 25, 2024
PubMed
Summary
This summary is machine-generated.

A new "Azide-Wittig" reaction enables versatile synthesis of triazabutadienes (TBDs). This method efficiently couples various organic azides and aldehydes, offering a valuable tool for tuning molecular properties.

Keywords:
AzidesOrganic SynthesisPhosphaalkenesTriazabutadienesWittig Reaction

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Heteroatom incorporation tunes organic molecule properties.
  • Triazabutadienes (TBDs) are interesting but lack general synthetic routes.

Purpose of the Study:

  • To develop a versatile synthetic protocol for triazabutadienes.
  • To explore the novel "Azide-Wittig" reaction pathway.

Main Methods:

  • Utilized a sterically hindered azide (Mes*N3) and phosphine (PMe3) with aromatic aldehydes.
  • Investigated reaction mechanisms using computational methods.

Main Results:

  • Developed the "Azide-Wittig" reaction, a versatile TBD synthesis.
  • Demonstrated tolerance for diverse aldehydes and organic azides.
  • Computational studies rationalized the shift from aza-Wittig to azide-Wittig reactivity.

Conclusions:

  • The "Azide-Wittig" reaction provides a new, adaptable method for TBD synthesis.
  • Kinetic control dictates reaction pathways, enabling selective azide-Wittig outcomes.