TY - JOUR
T1 - Investigation of the [1,7] Sigmatropic Hydrogen Shift in a Parent Compound Z,Z‐1,3,5‐Heptatriene and Its Monodeuterium Analogue
AU - Gurskii, Mikhail E.
AU - Gridnev, Ilya D.
AU - Il'ichev, Yuri V.
AU - Ignalenko, Anatoly V.
AU - Bubnov, Yuri N.
PY - 1992/6
Y1 - 1992/6
N2 - 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.)
AB - 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.)
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U2 - 10.1002/anie.199207811
DO - 10.1002/anie.199207811
M3 - Article
AN - SCOPUS:33748243750
VL - 31
SP - 781
EP - 783
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 6
ER -