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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. Mechanistic investigation and synthetic application were established in the 1960s…

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Overview

Mechanistic overview

Frontier molecular orbital theory

Stereospecificity

Diastereoselectivity

Regioselectivity

Synthetic applications

Biological applications

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1,3-Dipolar cycloaddition

Nodes203
Edges202
Triples91
Avg. degree1.99
Density0.009852
Components1

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1,3-Dipolar cycloaddition

Top relations

related to Frontier molecular orbital theory · 14
1,3-Dipolar cycloaddition → Dewar-Zimmerman, Dipolar, FMO, Hoffmann, HOMO, However, Huckel, II, III, In, LUMO, Such, The, Woodward
related to Diastereoselectivity · 11
1,3-Dipolar cycloaddition → Diels-Alder, Examples, First, In, Last, N-benzylide, Second, The, This, Unfortunately, When
has effect · 8
1,3-Dipolar cycloaddition → Dipolar, DMSO, For, Lack, N-cyclohexenyl, N-cyclopentenyl, On, The
related to Pericyclic mechanism · 8
1,3-Dipolar cycloaddition → Diels-Alder, Different, Huisgen, Solvent, Stereochemistry, Substituent, The, Thermodynamic
related to overview · 6
1,3-Dipolar cycloaddition → After, Firestone, However, Huckel, Originally, Rolf Huisgen
has application · 5
1,3-Dipolar cycloaddition → Additionally, Huisgen, Several, The, These
related to Nitrile oxides · 5
1,3-Dipolar cycloaddition → Both, Claisen-type, Cycloaddition, Miyakolide, Nitrile
related to With respect to dipole · 5
1,3-Dipolar cycloaddition → Diastereopure, Generally, However, If, These
related to Dipolarophile · 4
1,3-Dipolar cycloaddition → Heteroatom-containing, Other, Prato, The
is a · 2
1,3-Dipolar cycloaddition → chemical reaction between a 1, important route to the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives

Important terminology Word statistics

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Important terminology

cycloaddition reaction carbonyl 3-dipolar dipolarophile ylide dipolarophiles reactions homo dipole ylides metal lumo steric mechanism cycloadditions synthesis alkyne also methyl

Entity relationships Subject–Predicate–Object triples

SubjectPredicateObjectConfidenceSrc
1,3-Dipolar cycloadditionis achemical reaction between a 10.90text
1,3-Dipolar cycloadditionis aimportant route to the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives0.90text
sulfur or phosphorus are also knowninstance of3-Dipoles containing higher-row elements0.80text
but are utilized less routinely.Resonance structures can be drawn to delocalize both negativeinstance of3-Dipoles containing higher-row elements0.80text
positive charges onto any terminus of a 1instance of3-Dipoles containing higher-row elements0.80text
3-dipoleinstance of3-Dipoles containing higher-row elements0.80text
carbonylsinstance ofHeteroatom-containing dipolarophiles0.80text
imines can also undergo 1instance ofHeteroatom-containing dipolarophiles0.80text
3-dipolar cycloadditioninstance ofHeteroatom-containing dipolarophiles0.80text
the 1instance ofin which the diene LUMO combines with the dienophile HOMO.ReactivityConcerted processes0.80text
3-cycloaddition require a highly ordered transition stateinstance ofin which the diene LUMO combines with the dienophile HOMO.ReactivityConcerted processes0.80text
the 1instance ofReactivityConcerted processes0.80text

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