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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

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Volume 89, Issue 6


Mechanistic study of stereoselectivity in azoalkane denitrogenations

Manabu Abe
  • Corresponding author
  • Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
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/ Sayaka Hatano
  • Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan
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Published Online: 2017-02-28 | DOI: https://doi.org/10.1515/pac-2016-1215


Since 1965, the stereoselectivity in azoalkane denitrogenation has attracted much attention in both synthetic organic chemistry and physical organic chemistry. In this paper, a short review of the recent findings on the mechanism underlying the fascinating stereoselectivity in azoalkane denitrogenation is presented. The two types of singlet diradicals, i.e. the puckered and planar conformations, were found to play important roles in the stereoselectivity in the photochemical denitrogenation of cyclic azoalkanes. The presence of the puckered singlet diradical, which is the third isomer in homolysis, resolves the mechanistic puzzle reported so far for the stereoselectivity in azoalkane denitrogenations.

Keywords: azoalkanes; denitrogenation; ICPOC-23; singlet diradical; stereoselectivity

Article note:

A collection of invited papers based on presentations at the 23rd IUPAC Conference on Physical Organic Chemistry (ICPOC-23), Sydney, Australia, 3–8 July 2016.


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About the article

Published Online: 2017-02-28

Published in Print: 2017-06-27

Citation Information: Pure and Applied Chemistry, Volume 89, Issue 6, Pages 759–764, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2016-1215.

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