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

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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.
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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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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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1,3-Dipolar Cycloaddition with Diazo Groups: Noncovalent Interactions Overwhelm Strain.

Brian Gold1, Matthew R Aronoff1, Ronald T Raines1,2

  • 1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin, 53706, United States.

Organic Letters
|September 7, 2016
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Summary

Diazoacetamides and azides participate in 1,3-dipolar cycloadditions. Reactions with fluoro-substituted alkynes are significantly faster than with strained oxanorbornadienes due to favorable fluoro group interactions.

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Area of Science:

  • Organic Chemistry
  • Click Chemistry
  • Reaction Kinetics

Background:

  • 1,3-Dipolar cycloadditions are versatile reactions in organic synthesis.
  • Strain-accelerated cycloadditions, like those involving azides and cyclooctynes, are highly efficient.
  • Oxanorbornadienes (OND) are strained dipolarophiles used in cycloaddition reactions.

Purpose of the Study:

  • To investigate the reaction kinetics of diazoacetamides in 1,3-dipolar cycloadditions.
  • To compare the reactivity of diazoacetamides with strained oxanorbornadienes and unstrained fluoroalkynes.
  • To elucidate the role of fluoro groups in accelerating cycloaddition reactions.

Main Methods:

  • Studied the 1,3-dipolar cycloaddition of diazoacetamides with oxanorbornadienes.
  • Investigated the cycloaddition of diazoacetamides with ethyl 4,4,4-trifluoro-2-butynoate.
  • Determined the rate constant for the reaction in methanol.

Main Results:

  • Diazoacetamides undergo 1,3-dipolar cycloadditions with oxanorbornadienes, accelerated by strain relief.
  • The cycloaddition with ethyl 4,4,4-trifluoro-2-butynoate was 35-fold faster than with analogous OND.
  • Favorable interactions with fluoro groups significantly accelerated the reaction, with a rate constant of 0.53 M(-1) s(-1).

Conclusions:

  • Fluoro-substituted alkynes can be highly reactive partners in diazoacetamide cycloadditions.
  • The acceleration observed is attributed to favorable interactions with fluoro groups, not strain relief.
  • The reaction kinetics are comparable to strain-promoted azide-alkyne cycloadditions, highlighting its potential in click chemistry.