Investigation of the [1,7] Sigmatropic Hydrogen Shift in a Parent Compound Z,Z‐1,3,5‐Heptatriene and Its Monodeuterium Analogue

Mikhail E. Gurskii, Ilya D. Gridnev, Yuri V. Il'ichev, Anatoly V. Ignalenko, Yuri N. Bubnov

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An experimental confirmation of theoretical predictions is provided by this study of the sigmatropic [1,7] hydrogen shift in 1. Kinetic measurements on the monodeuterium analogue yielded an activation energy of 87 ± 3 kJ mol−1 and a frequency factor of 1.6 × 108 s−1. A comparison of these values with those for (Z)‐l,3‐pentadiene (152 and 2.8 × 1011, respectively) confirms the prediction that [1,7] hydrogen shifts should have a smaller activation energy and a more negative activation entropy than [1,5] hydrogen shifts. (Figure Presented.)

Original languageEnglish
Pages (from-to)781-783
Number of pages3
JournalAngewandte Chemie International Edition in English
Volume31
Issue number6
DOIs
Publication statusPublished - 1992 Jun
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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