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Related Experiment Videos

The allylic azide rearrangement: achieving selectivity.

Alina K Feldman1, Benoît Colasson, K Barry Sharpless

  • 1Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.

Journal of the American Chemical Society
|September 30, 2005
PubMed
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Allylic azides rearrange to isomers, often yielding product mixtures. However, selective reactions like copper-catalyzed cycloadditions can yield single products by exploiting subtle reactivity differences.

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms

Background:

  • Allylic azides are known to undergo rapid [3.3]-sigmatropic rearrangements.
  • These rearrangements lead to a dynamic equilibrium of multiple isomers.
  • Consequently, reactions involving allylic azides typically produce complex mixtures of products.

Purpose of the Study:

  • To investigate methods for achieving selective reactions with allylic azides.
  • To demonstrate how small differences in isomer reactivity can be amplified for product control.

Main Methods:

  • Exploration of copper(I)-catalyzed cycloaddition reactions with alkynes.
  • Investigation of epoxidation reactions using meta-chloroperoxybenzoic acid (MCPBA).

Main Results:

Related Experiment Videos

  • Copper(I)-catalyzed cycloaddition selectively reacts with primary and secondary allylic azide isomers.
  • MCPBA epoxidation preferentially targets allylic azide isomers with electron-rich double bonds.
  • These selective reactions allow for the isolation of single products in high yields.

    • Conclusions:

    • Despite the inherent complexity of allylic azide rearrangements, selective synthetic strategies can overcome mixture formation.
    • Exploiting differential reactivity of azide isomers enables controlled synthesis of specific products.
    • This work provides valuable insights for designing selective transformations of allylic azides.