• Source: 1,3-dipole

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. They are reactants in 1,3-dipolar cycloadditions.
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.

Known 1,3-dipoles are:

Azides (RN3)
Ozone (O3)
Nitro compounds (RNO2)
Diazo compounds (R2CN2)
Some oxides
Azoxide compounds (RN(O)NR)
Carbonyl oxides (Criegee zwitterions)
Nitrile oxides (RCN−O)
Nitrous oxide (N2O)
Nitrones (R2CN(R)O)

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

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• 1,3-dipole
• 1,3-Dipolar cycloaddition
• Aziridines
• Azide-alkyne Huisgen cycloaddition
• Azomethine ylide
• Nitrone
• Ylide
• Dipolar compound
• Montréalone
• Diazoalkane 1,3-dipolar cycloaddition