The Stieglitz rearrangement is a rearrangement reaction in organic chemistry which is named after the American chemist Julius Stieglitz (1867–1937) and was first investigated by him and Paul Nicholas Leech in 1913.[1] It describes the 1,2-rearrangement of trityl amine derivatives to triaryl imines.[1][2] It is comparable to a Beckmann rearrangement which also involves a substitution at a nitrogen atom through a carbon to nitrogen shift.[3] As an example, triaryl hydroxylamines can undergo a Stieglitz rearrangement by dehydration and the shift of a phenyl group after activation with phosphorus pentachloride to yield the respective triaryl imine, a Schiff base.[4][5]
Stieglitz Rearrangement hydroxylamines
In general, the term "Stieglitz rearrangement" is used to describe a wide variety of rearrangement reactions of amines to imines.[4] Although, it is generally associated with the rearrangement of triaryl hydroxylamines, that are well-reported in the academic literature, Stieglitz rearrangements can also occur on alkylated amine derivatives,[6] haloamines[7][8] and azides[9][10] as well as other activated amine derivatives.[4]
^ abJulius Stieglitz, Paul Nicholas Leech (1914). "The molecular Rearrangement of Triarylmethyl-Hydroxylamines and the Beckmann Rearrangement of Ketoximes". Journal of the American Chemical Society. 36 (2): 272–301. doi:10.1021/ja02179a008.
^Bert Allen Stagner (1914). "The molecular Rearrangement of Triarylmethyl-Hydroxylamines". Journal of the American Chemical Society. 36 (2): 2069–2081. doi:10.1021/ja02267a018.
^Wang, Zerong (2010). Comprehensive organic name reactions and reagents. John Wiley & Sons, Inc. pp. 288–295. ISBN 9780471704508.
^ abcCite error: The named reference Wang-2010 was invoked but never defined (see the help page).
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "Schiff base". doi:10.1351/goldbook.S05498
^Cite error: The named reference Grieco-1998 was invoked but never defined (see the help page).
^Cite error: The named reference Vosburgh-1916 was invoked but never defined (see the help page).
^Cite error: The named reference Hilton-1950 was invoked but never defined (see the help page).
^Morgan, Agnes Fay (October 1916). "The Molecular Rearrangements of some Triaryl-Methylchloroamines". Journal of the American Chemical Society. 38 (10): 2095–2101. doi:10.1021/ja02267a020.
^Kuhn, James (December 1916). "The Molecular Rearrangement of Triarylmethylazides". Journal of the American Chemical Society. 38 (12): 2718–2726. doi:10.1021/ja02269a014.
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