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. They are reactants in 1,3-dipolar cycloadditions.^[1] ^[2]

Known 1,3-dipoles are:

- Azoxide compounds
- Carbonyl oxides (Criegee zwitterions)^[3]^[4]
- Nitrile oxides
- Nitrous oxide
- Nitrones
Some imines:
- Azomethine imine
- Nitrilimines
- Carbonyl imines
Some ylides
- Azomethine ylide
- Nitrile ylide
- Carbonyl ylide

References

^ Francis A. Carey, Richard J. Sundberg (2007). "Part A: Structure and mechanisms". Advanced Organic Chemistry (5, illustrated ed.). Springer. p. 874. ISBN 9780387448978.
^ IUPAC Gold Book dipolar compounds
^ http://www.organic-chemistry.org/namedreactions/ozonolysis-criegee-mechanism.shtm Ozonolysis mechanism on Organic Chemistry Portal site
^ Li, Jie Jack: Criegee mechanism of ozonolysis Book: Name Reactions. 2006, 173-174, doi:10.1007/3-540-30031-7_77