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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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.
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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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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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...
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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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Boryl azides in 1,3-dipolar cycloadditions.

Matthias Müller1, Cäcilia Maichle-Mössmer, Holger F Bettinger

  • 1Institut für Organische Chemie, Universität Tübingen , Auf der Morgenstelle 18, 72076 Tübingen, Germany.

The Journal of Organic Chemistry
|May 29, 2014
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Boron azides undergo 1,3-dipolar cycloaddition reactions with alkynes. Tricoordinate boron azides act as type II dipoles, while tetracoordinate boron azides are electron-rich type I dipoles.

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Area of Science:

  • Organic Chemistry
  • Organoboron Chemistry
  • Cycloaddition Reactions

Background:

  • 1,3-dipolar cycloaddition reactions are fundamental in organic synthesis.
  • Boron azides are versatile reagents with unique electronic properties.
  • Understanding the reactivity of boron azides with alkynes is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To investigate the 1,3-dipolar cycloaddition reaction between boron azides and alkynes.
  • To elucidate the influence of boron coordination number on the reaction mechanism and regioselectivity.
  • To characterize the resulting triazole products and their derivatives.

Main Methods:

  • Experimental studies involving the reaction of pinacolato boron azide (pinBN3) with cyclooctyne.
  • Alcoholysis of the resulting oligomeric boryl triazole.
  • X-ray crystallography for structural characterization of the cyclooctatriazole hydrate.
  • Computational analysis of reactions involving various tri- and tetracoordinate boron azides.

Main Results:

  • Pinacolato boron azide (pinBN3) reacts with cyclooctyne to form an oligomeric boryl triazole.
  • Alcoholysis yields 4,5,6,7,8,9-hexahydro-2H-cyclooctatriazole, characterized as a hydrate.
  • Tricoordinate boron azides function as type II 1,3-dipoles.
  • Tetracoordinate IMe·H2BN3 acts as an electron-rich type I 1,3-dipole, favoring reactions with electron-poor alkynes.

Conclusions:

  • The coordination number of boron significantly impacts the reactivity of boron azides in 1,3-dipolar cycloaddition reactions.
  • Tricoordinate boron azides exhibit different reactivity patterns compared to tetracoordinate boron azides.
  • This study provides insights into the mechanistic pathways and synthetic utility of boron azide cycloadditions.