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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. It describes the 1,2-rearrangement of trityl amine derivatives to triaryl imines. It is comparable to a Beckmann rearrangement which also involves a substitution at a nitrogen atom through a carbon to nitrogen shift. 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.

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  • Stieglitz-Umlagerung (de)
  • Stieglitz rearrangement (en)
  • 施蒂格利茨重排反应 (zh)
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  • Die Stieglitz-Umlagerung ist eine Namensreaktion in der Organischen Chemie und wurde im Jahre 1913 von den Chemikern Julius Stieglitz und beschrieben. Es handelt sich dabei eine Synthesemethode zur Herstellung von Imin-Derivaten. (de)
  • 施蒂格利茨重排反应（Stieglitz rearrangement）指三芳甲基羟胺（Ar3CNHOH）重排为三芳基亚胺。 (zh)
  • 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. It describes the 1,2-rearrangement of trityl amine derivatives to triaryl imines. It is comparable to a Beckmann rearrangement which also involves a substitution at a nitrogen atom through a carbon to nitrogen shift. 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. (en)
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  • Stieglitz rearrangement (en)
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  • http://commons.wikimedia.org/wiki/Special:FilePath/General_mechanism_Stieglitz_rearrangement.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Lycopodine_total_synthesis_final_step.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/StieglitzRearrangementhydroxylamines.svg
  • http://commons.wikimedia.org/wiki/Special:FilePath/Stieglitz_Tosylate_Bredt_rule.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Stieglitz_rearrangement_N-haloamines.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Stieglitz_rearrangement_PCl5.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Stieglitz_rearrangement_benzyloxy_substituted_amine.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Beckmann-rearrangement_mechanism.svg
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  • Rearrangement reaction (en)
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  • Die Stieglitz-Umlagerung ist eine Namensreaktion in der Organischen Chemie und wurde im Jahre 1913 von den Chemikern Julius Stieglitz und beschrieben. Es handelt sich dabei eine Synthesemethode zur Herstellung von Imin-Derivaten. (de)
  • 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. It describes the 1,2-rearrangement of trityl amine derivatives to triaryl imines. It is comparable to a Beckmann rearrangement which also involves a substitution at a nitrogen atom through a carbon to nitrogen shift. 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. In general, the term "Stieglitz rearrangement" is used to describe a wide variety of rearrangement reactions of amines to imines. 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, haloamines and azides as well as other activated amine derivatives. (en)
  • 施蒂格利茨重排反应（Stieglitz rearrangement）指三芳甲基羟胺（Ar3CNHOH）重排为三芳基亚胺。 (zh)
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