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.
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)
