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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.7K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
21.7K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.9K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.9K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.0K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
5.0K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.8K
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 para...
3.8K

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Study of O-Allylation Using Triazine-Based Reagents.

Kohei Yamada1, Naoko Hayakawa, Hikaru Fujita

  • 1Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University.

Chemical & Pharmaceutical Bulletin
|January 5, 2017
PubMed
Summary
This summary is machine-generated.

New acid-catalyzed allylating reagents, 2,4,6-tris(allyloxy)-1,3,5-triazine (TriAT-allyl) derivatives, efficiently convert acid-labile alcohols into allyl ethers. This method offers a reliable route for synthesizing valuable allyl ether compounds.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Allyl ethers are versatile synthetic intermediates.
  • Developing efficient methods for their synthesis is crucial in organic chemistry.

Purpose of the Study:

  • To develop novel acid-catalyzed allylating reagents.
  • To synthesize allyl ethers from acid- and alkali-labile alcohols.

Main Methods:

  • Synthesis of 2,4,6-tris(allyloxy)-1,3,5-triazine (TriAT-allyl) and its derivatives.
  • Acid-catalyzed reaction of alcohols with TriAT-allyl using trifluoromethanesulfonic acid (TfOH).

Main Results:

  • TriAT-allyl reagents efficiently produced allyl ethers from various alcohols in good yields.
  • The reaction proceeded under mild acidic conditions.
  • Studies with regioisomeric allyl groups suggest a single allylic cation intermediate.

Conclusions:

  • TriAT-allyl reagents represent a new class of effective allylating agents.
  • This method provides a facile route to allyl ethers, particularly from sensitive alcohols.
  • The findings shed light on the reaction mechanism involving allylic cations.