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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Related Experiment Video

Updated: Jun 2, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

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Dioxazaborocanes: old adducts, new tricks.

Hélène Bonin1, Thomas Delacroix, Emmanuel Gras

  • 1CNRS, Université Paul Sabatier, LSPCMIB, 118, route de Narbonne, F-31062 Toulouse Cedex 9. helene.bonin@yahoo.fr

Organic & Biomolecular Chemistry
|May 4, 2011
PubMed
Summary

Dioxazaborocanes, boronic adducts, are emerging as versatile reagents in chemical transformations. They offer a practical, fluoride-free alternative to organotrifluoroborate salts, indicating a significant area for future research and development.

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Area of Science:

  • Organic Chemistry
  • Organoboron Chemistry

Background:

  • Dioxazaborocanes are boronic adducts formed from diethanolamine derivatives and boronic compounds.
  • Historically, their use was limited to isolating and characterizing boronic acids or intermediates.
  • Recent studies highlight their direct application in chemical reactions.

Purpose of the Study:

  • To demonstrate the utility of dioxazaborocanes in chemical transformations.
  • To present dioxazaborocanes as a protected form of boronic acids.
  • To establish dioxazaborocanes as a fluoride-free alternative to organotrifluoroborate salts.

Main Methods:

  • Condensation reactions of diethanolamine derivatives with boronic compounds.
  • Utilizing dioxazaborocanes in direct chemical transformations.
  • Comparing the efficacy of dioxazaborocanes with their boronic acid counterparts.

Main Results:

  • Dioxazaborocanes have shown equivalence or superiority to boronic acids in certain reactions.
  • They serve effectively as protected boronic acids.
  • Their potential as a fluoride-free alternative to organotrifluoroborate salts is evident.

Conclusions:

  • Dioxazaborocanes are valuable reagents with expanding applications beyond simple isolation.
  • They represent a promising fluoride-free alternative in organoboron chemistry.
  • Further development in dioxazaborocane chemistry is anticipated.