Beckmann Rearrangements and Fragmentations in Organic Synthesis

Trinh A.D. Holth, Oliver E. Hutt, Gunda I. Georg

Research output: Chapter in Book/Report/Conference proceedingChapter

6 Scopus citations


This chapter covers the different transformations, provides some important historical examples of the utility of Beckmann reactions in the total synthesis of natural products. It examines novel strategic applications and their synthetic utility with a focus on those examples from the past decade until February 2014. Incorporation of the Beckmann reaction during retrosynthetic analysis can be a powerful method for planning carbon-nitrogen bond installation or ring expansion. The chapter presents examples that show the versatility of the Beckmann reaction in the formation of novel structures by exploring the ent-kaurene skeleton of stevioside. Another aspect of the Beckmann reaction is its ability to form different scaffolds through an intramolecular nucleophile-trapping mechanism. Using the Beckmann reactions can generate diverse nitrogen-containing heterocycles and a number of different functional groups that are useful for other chemical transformations.

Original languageEnglish (US)
Title of host publicationMolecular Rearrangements in Organic Synthesis
Number of pages39
ISBN (Electronic)9781118939901
ISBN (Print)9781118347966
StatePublished - Oct 12 2015

Bibliographical note

Publisher Copyright:
© 2015 John Wiley & Sons, Inc.


  • Beckmann fragmentations
  • Beckmann rearrangements
  • Functional groups
  • Heterocyclic scaffolds
  • Natural products
  • Organic synthesis
  • Ring expansion


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