The Effect of Proximal Functionality on the Allylic Azide Equilibrium

Mary H. Packard, James H. Cox, Victoria P. Suding, Joseph J. Topczewski

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11 Scopus citations


This report describes an investigation into the effect that proximal functionality has on the allylic azide equilibrium. We report 16 allylic azides with varied functionality from three subclasses. We observe a correlation of % branched azide to the pKa of the OR group. We also observe that RN–H azides have a higher % branched azide relative the corresponding RN–Bn compound. These two effects combine to describe the observed equilibrium for the known compound hydroxy-crotyl azide. DFT calculations support several stereoelectronic effects that contribute to the relative energetics.

Original languageEnglish (US)
Pages (from-to)6365-6368
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number43
StatePublished - Nov 24 2017

Bibliographical note

Funding Information:
We are grateful for helpful discussions with Grace Gast and Prof. Steve Kass. We gratefully acknowledge the University of Minnesota and the American Chemical Society's Petroleum Research Fund (PRF # 56505-DNI1) for financial support. The Minnesota Supercomputing Institute (MSI) at the University of Minnesota provided resources that contributed to the results reported within this paper.

Publisher Copyright:
© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim


  • Amines
  • Azides
  • Click chemistry


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