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Related Experiment Videos

"It's a (Kinetic) Trap!" - Selectively Differentiating Allylic Azide Isomers.

Joseph J Topczewski1, Matthew R Porter1

  • 1Department of Chemistry, University of Minnesota - Twin Cities, 207 Pleasant St. SE, Minneapolis MN 55455, USA.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
|December 4, 2018
PubMed
Summary

Allylic azides undergo the Winstein rearrangement, but controlling isomers is difficult. This study presents new methods for selectively trapping these reactive intermediates in synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Allylic azides are known to undergo the Winstein rearrangement, forming equilibrating isomer mixtures.
  • Despite being known for decades, the Winstein rearrangement of allylic azides has limited synthetic applications due to challenges in isomer differentiation.

Purpose of the Study:

  • To develop novel synthetic methodologies for selectively trapping allylic azide isomers.
  • To overcome the lack of selectivity in exploiting allylic azides in organic synthesis.

Main Methods:

  • Investigating the Winstein rearrangement of allylic azides.
  • Developing strategies for selective trapping of specific allylic azide isomers.

Main Results:

  • Demonstrated progress in leveraging the Winstein rearrangement into practical synthetic methods.
Keywords:
allylicazidescyclizationdynamic kinetic resolutionstereoselectivesynthesis

Related Experiment Videos

  • Achieved selective trapping of allylic azides, enabling differentiation of isomers.

    • Conclusions:

    • The developed methods offer new possibilities for utilizing allylic azides in complex molecule synthesis.
    • Advances in selectivity pave the way for broader synthetic applications of the Winstein rearrangement.