Publication: Aromatische [1,5s]-sigmatropische H-Verschiebungen in Arylallenen
Aromatische [1,5s]-sigmatropische H-Verschiebungen in Arylallenen
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Heimgartner, H., Zsindely, J., Hansen, H.-J., & Schmid, H. (1973). Aromatische [1,5s]-sigmatropische H-Verschiebungen in Arylallenen. Helvetica Chimica Acta, 56(8), 2924–2945. https://doi.org/10.1002/hlca.19730560833
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Abstract
1-Mesitylallene (1), 1-mesityl-3-methylallene (2) and 1-mesityl-3,3-dimethyl allene (3) rearrange thermally at 150-190° in decane via [1,5s]sigmatropic H-shifts to yield the o-quinodimethanes 4, which cyclise to give the 1,2-dihydronaphthalenes 5 and 6 and/or undergo [1,7a]sigmatropic H-shifts to give 1-mesityl-(Z)-buta-1,3-dienes (Z)-7 and (Z)-8, respectively (Schemes 1, 3, 4 and 5) in almost quantitative yields.The activation parameters of these isomerisations are given in Table1. 1-Mesityl-1-methylallenc (9) isomerises at 190° to g
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- Heimgartner, Heinz
- Zsindely, Janos
- Hansen, Hans-Jürgen
- Schmid, Hans
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Heimgartner, H., Zsindely, J., Hansen, H.-J., & Schmid, H. (1973). Aromatische [1,5s]-sigmatropische H-Verschiebungen in Arylallenen. Helvetica Chimica Acta, 56(8), 2924–2945. https://doi.org/10.1002/hlca.19730560833
