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1,3-Dipolar Cycloaddition Chemistry

24 May 1984-
TL;DR: The theory of 1-3-Dipolar Cycloadditions is discussed in this article. But it does not consider higher-order cycloaddings and higher order cycloreversions.
Abstract: Historical Note, General Principle and Mechanistic Criteria. Nitrile Ylides. Nitrile Oxides and Nitrile Imines. Diazoalkanes. Azides and Nitrous Oxide. Azomethine Ylides. Azomethine Imines. Mesoionic Ring Systems. Nitrones. Azimines, Azoxy Compounds and Nitro Compounds. Ozone and Carbonyl Oxides. Intramolecular Dipolar Cycloadditions. Theory of 1,3--Dipolar Cycloadditions. 1,3--Dipolar Cycloreversions. Higher Order Dipolar Cycloadditions.
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Journal ArticleDOI
TL;DR: The copper-(I)-catalyzed 1,2,3-triazole formation from azides and terminal acetylenes is a particularly powerful linking reaction, due to its high degree of dependability, complete specificity, and the bio-compatibility of the reactants.

2,882 citations

Journal ArticleDOI
TL;DR: The bioorthogonal chemical reactions developed to date are described and how they can be used to study biomolecules.
Abstract: The study of biomolecules in their native environments is a challenging task because of the vast complexity of cellular systems. Technologies developed in the last few years for the selective modification of biological species in living systems have yielded new insights into cellular processes. Key to these new techniques are bioorthogonal chemical reactions, whose components must react rapidly and selectively with each other under physiological conditions in the presence of the plethora of functionality necessary to sustain life. Herein we describe the bioorthogonal chemical reactions developed to date and how they can be used to study biomolecules.

2,537 citations


Cites background from "1,3-Dipolar Cycloaddition Chemistry..."

  • ...The product of an azide–alkene cycloaddition is a triazoline, which is relatively unstable compared to an aromatic triazole and is not advantageous for applications where a ligation product is desired.[167] Rutjes and co-workers circumvented this problem by using oxanorbornadienes containing electron-deficient olefins (21) as substrates....

    [...]

  • ...[165] Nevertheless, the potential of this transformation, especially the cycloaddition of azides and alkynes to form aromatic triazole products (ΔG° ≈ −61 kcalmol−1),[166] was too great for it to be overlooked.[167]...

    [...]

Journal ArticleDOI
TL;DR: The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties.
Abstract: The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand. The process has been employed to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties. The chelating ligand plays a crucial role in stabilizing the Cu(I) oxidation state and protecting the protein from Cu(triazole)-induced denaturation. Because the azide and alkyne groups themselves are unreactive with protein residues or other biomolecules, their ligation is of potential utility as a general bioconjugation method.

1,602 citations

Journal ArticleDOI
TL;DR: There are several methods for the dispersion of CNTs in the polymer matrix such as solution mixing, melt mixing, electrospinning, in-situ polymerization and chemical functionalization of the carbon nanotubes as discussed by the authors.

1,503 citations