1,3-dipole
Appearance
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From top to bottom, azides, nitrones, and nitro compounds are examples of 1,3-dipoles. |
In
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.[3]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/f/f3/1%2C3-dipolar_compounds.png/402px-1%2C3-dipolar_compounds.png)
Known 1,3-dipoles are:
- Azides (RN3)
- Ozone (O3)
- Nitro compounds (RNO2)
- Diazo compounds (R2CN2)
- Some oxides
- Azoxide compounds (RN(O)NR)
- Nitrile oxides(RCN−O)
- Nitrous oxide (N2O)
- Nitrones (R2CN(R)O)
![](http://upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Carbonyl_oxide-resonance.svg/220px-Carbonyl_oxide-resonance.svg.png)
- Some imines:
- Azomethine imine
- Nitrilimines (RCN−NR, analogous to nitrile oxide)
- Carbonyl imines
- Some ylides
- Azomethine ylide
- Nitrile ylide (RCNCR'2)
- Carbonyl ylide
- Thiosulfines (R2CSS)
References
- ISBN 978-0-387-44897-8.
- ^ IUPAC Gold Book dipolar compounds
- ISBN 978-1906574161.
- ^ https://www.organic-chemistry.org/namedreactions/ozonolysis-criegee-mechanism.shtm Ozonolysis mechanism on Organic Chemistry Portal site