Iminium
Iminium ions and iminium cations are resonance-stabilized organic cations having a bond between a nitrogen atom and a carbon atom.
Reactions in which iminium ions are formed as intermediates ( selection)
- Beckmann rearrangement
- Duff reaction
- Fragmentation of ionized amines via an α - cleavage in the mass spectrometer
- Leuckart - Wallach reaction
- Mannich reaction
- Pinner reaction
- Pictet -Spengler reaction
- Ugi reaction
- Vilsmeier -Haack reaction
Production and reserves
Iminium ions formed as an intermediate, for example, in the dehydration of hemiaminals. Often also referred to as a " protonated imine ", when talking about an iminium ion. This name comes from the fact that imines leads to the formation iminium ion. The iminium ion undergoes resonance, which affects its reactivity. A mesomeric form is then a carbenium ion. Chloride salts of N-acylated iminium ions formed in the reaction of imines with carboxylic acid chlorides.
Examples
Since the iminium ion can have very different shapes, are here now Several examples are given to illustrate the variety of possibilities.
Iminium ion intermediate in the Pictet -Spengler reaction
Iminium ion intermediate in the Mannich reaction
Iminumchloridsalz, also called Pinner salt as formed in the Pinner reaction
See also
- Ammonium