1,3-dipole
| From top to bottom, azides, nitrones, and nitro compounds are examples of 1,3-dipoles. |
In organic chemistry, a 1,3-dipolar compound or 1,3-dipole is a dipolar compound with delocalized electrons and a separation of charge over three atoms, as follows: the dipole has at least one resonance structure with positive and negative charges having a 1,3 relationship which can generally be denoted as, where a may be a carbon, oxygen or nitrogen, b may be nitrogen or oxygen, and c may be a carbon, oxygen or nitrogen.
They are reactants in 1,3-dipolar cycloadditions.
Known 1,3-dipoles are:
- Azides
- Ozone
- Nitro compounds
- Diazo compounds
- Some oxides
- * Azoxide compounds
- * Carbonyl oxides
- * Nitrile oxides
- * Nitrous oxide
- * Nitrones
- Some imines:
- * Azomethine imine
- * Nitrilimines
- * Carbonyl imines
- Some ylides
- * Azomethine ylide
- * Nitrile ylide
- * Carbonyl ylide
- * Thiosulfines