Beckmann rearrangement [SEP] named after
Beckmann rearrangement
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. The rearrangement has also been successful performed on haloimines and nitrones. Cyclic oximes and haloimines yield lactams.
The Beckmann rearrangement is often catalyzed by acid, however other reagents have been known to promote the rearrangement. These include tosyl chloride, thionyl chloride, phosphorus pentachloride, phosphorus pentoxide, triethylamine, sodium hydroxide, trimethylsilyl iodide among others. The Beckmann fragmentation is another
.
Reactions Named reactions involving iminium species.
- Aza-Cope rearrangement
- Beckmann rearrangement
- Duff reaction
- Mannich reaction
- Pictet-Spengler reaction
- Stephen reaction
- Stork enamine alkylation
- Vilsmeier-Haack reaction and Vilsmeier reagent
Iminylium ions.
Iminylium ions have the general structure RC=N. They form a subclass of nitrenium ions.
See also.
- Ammonium