Stieglitz rearrangement
Encyclopedia
The Stieglitz rearrangement is a rearrangement reaction
of a trityl hydroxylamine
Ar3CNHOH to a triaryl imine
. The reaction is related to the Beckmann rearrangement
as both reaction involve a carbon to nitrogen shift.
Rearrangement reaction
A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule...
of a trityl hydroxylamine
Hydroxylamine
Hydroxylamine is an inorganic compound with the formula NH2OH. The pure material is a white, unstable crystalline, hygroscopic compound. However, hydroxylamine is almost always provided and used as an aqueous solution. It is used to prepare oximes, an important functional group. It is also an...
Ar3CNHOH to a triaryl imine
Imine
An imine is a functional group or chemical compound containing a carbon–nitrogen double bond, with the nitrogen attached to a hydrogen atom or an organic group. If this group is not a hydrogen atom, then the compound is known as a Schiff base...
. The reaction is related to the Beckmann rearrangement
Beckmann rearrangement
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann , is an acid-catalyzed rearrangement of an oxime to an amide...
as both reaction involve a carbon to nitrogen shift.