umpolung
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In organic chemistry, umpolung () or polarity inversion is the chemical modification of a functional group with the aim of the reversal of polarity of that group. This modification allows secondary reactions of this functional group that would otherwise not be possible. The concept was introduced by D. Seebach (hence the German word for reversed polarity) and E.J. Corey. Polarity analysis during retrosynthetic analysis tells a chemist when umpolung tactics are required to synthesize a target molecule.
~9 min read
Article
12 sectionsContents
- Introduction
- Examples
- Cyanide-type umpolung
- N-heterocyclic carbenes
- Thiamine pyrophosphate
- 3-membered rings
- Carbonyl umpolung / anion relay chemistry
- Oxidative bond formation
- Amine umpolung
- Hydrazone umpolung
- References
- External links
In organic chemistry, umpolung () or polarity inversion is the chemical modification of a functional group with the aim of the reversal of polarity of that group. This modification allows secondary reactions of this functional group that would otherwise not be possible. The concept was introduced by D. Seebach (hence the German word for reversed polarity) and E.J. Corey. Polarity analysis during retrosynthetic analysis tells a chemist when umpolung tactics are required to synthesize a target molecule.
==Introduction== The vast majority of important organic molecules contain heteroatoms, which polarize carbon skeletons by virtue of their electronegativity. Therefore, in standard organic reactions, the majority of new bonds are formed between atoms of opposite polarity. This can be considered to be the "normal" mode of reactivity.