Tandem [4+2]/[3+2] Cycloadditions

Ramil Y. Baiazitov, Scott E. Denmark

Research output: Chapter in Book/Report/Conference proceedingChapter


This chapter focuses on tandem cycloadditions that are initiated by a [4 + 2] cycloaddition step that generates a 1,3-dipole or a precursor to a 1,3-dipole, which then engages in a [3 + 2] cycloaddition. Compared to the cycloadditions of nitroalkenes, tandem cycloadditions of 1,3,4-oxadiazoles consist not of two, but of three elementary reactions. The major synthetic applications of the tandem cycloadditions of 1,3,4-oxadiazoles include construction of oligomeric ribbon-like or cavity molecules as well as syntheses of natural products. The chapter refines the definition of a tandem process and its three variants: cascade, consecutive, and sequential. The tandemcycloaddition of nitroalkenes is a very complex process consisting of a number of elementary reactions. The examples of the tandem cycloadditions of nitroalkenes reviewed here demonstrate a well-developed strategy that can and has been applied for syntheses of many natural and unnatural compounds.

Original languageEnglish (US)
Title of host publicationMethods and Applications of Cycloaddition Reactions in Organic Syntheses
Number of pages80
ISBN (Electronic)9781118778173
ISBN (Print)9781118299883
StatePublished - Feb 10 2014


  • Nitroalkenes
  • Oxadiazoles
  • Tandem cycloadditions
  • [3+2] cycloaddition
  • [4+2] cycloadditions

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering


Dive into the research topics of 'Tandem [4+2]/[3+2] Cycloadditions'. Together they form a unique fingerprint.

Cite this