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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 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
4.2K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

11.5K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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α-Substituted vinyl azides: an emerging functionalized alkene.

Junkai Fu1, Giuseppe Zanoni, Edward A Anderson

  • 1Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Northeast Normal University, Changchun 130024, China. bixh507@nenu.edu.cn.

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Vinyl azides, particularly α-substituted variants, offer diverse reactivity for synthesizing nitrogen-containing compounds. This review covers their preparation and versatile applications in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Heterocyclic Chemistry

Background:

  • Vinyl azides are valuable building blocks in organic synthesis.
  • α-Substituted vinyl azides exhibit unique reactivity beyond typical azide behavior.
  • These compounds serve as precursors to diverse nitrogen-containing molecules.

Purpose of the Study:

  • To review synthetic methods for accessing vinyl azides.
  • To comprehensively cover the multifaceted reactivity of vinyl azides.
  • To highlight their potential in synthetic applications.

Main Methods:

  • Exploitation of vinyl azides in cycloadditions.
  • Application in C-H functionalization reactions.
  • Utilizing intermediates like iminodiazonium ions and nitrilium ions.

Main Results:

  • Demonstration of vinyl azides as radical acceptors, nucleophiles, and electrophiles.
  • Generation of various reactive intermediates (iminyl radicals, metal enaminyl radicals).
  • Successful application under transition metal/photoredox catalysis.

Conclusions:

  • Vinyl azides are versatile synthons for N-heterocycles and other functional groups.
  • Their unique reactivity enables access to a wide array of nitrogen-containing compounds.
  • This review underscores their broad potential in synthetic chemistry.