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  2. 1,3-Dipolar cycloaddition - Wikipedia

    en.wikipedia.org/wiki/1,3-Dipolar_cycloaddition

    The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles.

  3. Cycloaddition - Wikipedia

    en.wikipedia.org/wiki/Cycloaddition

    In this notation, a Diels-Alder reaction is a (4+2)cycloaddition and a 1,3-dipolar addition such as the first step in ozonolysis is a (3+2)cycloaddition. The IUPAC preferred notation however, with [i+j+...] takes electrons into account and not atoms. In this notation, the DA reaction and the dipolar reaction both become a [4+2]cycloaddition.

  4. Azide-alkyne Huisgen cycloaddition - Wikipedia

    en.wikipedia.org/wiki/Azide-alkyne_Huisgen_cyclo...

    [3] Thermal Huisgen 1,3-dipolar cycloaddition. In the reaction above [4] azide 2 reacts neatly with alkyne 1 to afford the product triazole as a mixture of 1,4-adduct (3a) and 1,5-adduct (3b) at 98 °C in 18 hours. The standard 1,3-cycloaddition between an azide 1,3-dipole and an alkene as dipolarophile has largely been ignored due to lack of ...

  5. Nitrone-olefin (3+2) cycloaddition - Wikipedia

    en.wikipedia.org/wiki/Nitrone-olefin_(3+2...

    The nitrone-olefin (3+2) cycloaddition reaction is the combination of a nitrone with an alkene or alkyne to generate an isoxazoline or isoxazolidine via a (3+2) cycloaddition process. [1] This reaction is a 1,3-dipolar cycloaddition, in which the nitrone acts as the 1,3-dipole, and the alkene or alkyne as the dipolarophile.

  6. 1,3-dipole - Wikipedia

    en.wikipedia.org/wiki/1,3-dipole

    They are reactants in 1,3-dipolar cycloadditions. [ 1 ] [ 2 ] The dipole has at least one resonance structure with positive and negative charges having a 1,3 relationship which can generally be denoted as + a−b−c − , where a may be a carbon , oxygen or nitrogen , b may be nitrogen or oxygen, and c may be a carbon, oxygen or nitrogen.

  7. Diazoalkane 1,3-dipolar cycloaddition - Wikipedia

    en.wikipedia.org/wiki/Diazoalkane_1,3-dipolar_cy...

    The Diazoalkane 1,3-dipolar cycloaddition is a 1,3-dipolar cycloaddition (an organic reaction) between a 1,3-dipole diazo compound (notably diazomethane) and a dipolarophile. When the dipolarphile is an alkene , the reaction product is a pyrazoline .

  8. Azomethine ylide - Wikipedia

    en.wikipedia.org/wiki/Azomethine_ylide

    Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered heterocycles, including pyrrolidines and pyrrolines. [1] [2] [3] These reactions are highly stereo-and regioselective, and have the potential to form four new contiguous ...

  9. Prato reaction - Wikipedia

    en.wikipedia.org/wiki/Prato_reaction

    The amino acid sarcosine reacts with paraformaldehyde when heated at reflux in toluene to an ylide which reacts with a double bond in a 6,6 ring position in a fullerene via a 1,3-dipolar cycloaddition to yield a N-methylpyrrolidine derivative or pyrrolidinofullerene or pyrrolidino[[3,4:1,2]] [60]fullerene in 82% yield based on C 60 conversion.

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