Publication: Thermisches Verhalten von o-Dipropenylbenzol, Beispiel einer aromatischen [1,7]-sigmatropischen H-Verschiebung
Thermisches Verhalten von o-Dipropenylbenzol, Beispiel einer aromatischen [1,7]-sigmatropischen H-Verschiebung
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Heimgartner, H., Hansen, H.-J., & Schmid, H. (1970). Thermisches Verhalten von o-Dipropenylbenzol, Beispiel einer aromatischen [1,7]-sigmatropischen H-Verschiebung. Helvetica Chimica Acta, 53, 173–176. https://doi.org/10.1002/hlca.19700530124
Abstract
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Abstract
cis,cis-, cis,trans- and trans,trans-o-Dipropenylbenzene (cis,cis-, cis,trans- and trans,trans-1) were prepared. At 225° cis,cis-1 isomerises to give cis,trans-1 and vice versa. The isomerisation follows 1.order kinetics. At equilibrium 89% cis,trans- and 11% cis,cis-1 are present. It is shown by deuterium labelling that the isomerisation is due to aromatic [1,7a] sigmatropic H-shifts. trans,trans-1 rearranges at 225° to yield 2,3-dimethyl-1,2-dihydronaphthalene (3). This can be visualized by disrotatory ring closure of trans,trans-1
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- Heimgartner, Heinz
- Hansen, Hans-Jürgen
- Schmid, Hans
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Heimgartner, H., Hansen, H.-J., & Schmid, H. (1970). Thermisches Verhalten von o-Dipropenylbenzol, Beispiel einer aromatischen [1,7]-sigmatropischen H-Verschiebung. Helvetica Chimica Acta, 53, 173–176. https://doi.org/10.1002/hlca.19700530124
