1,3-dipole
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| 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:
- Azides
- Ozone
- Nitro compounds
- Diazo compounds
- Some oxides
- Azoxide compounds
- Carbonyl oxides (Criegee zwitterions)[3][4]
- Nitrile oxides
- Nitrous oxide
- Nitrones
Carbonyl oxide
- 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 978-0-387-44897-8.
- ↑ 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