Publication: Die Dienol-Benzol-Umlagerung von Propargylcyclohexadienolen: aromatische [1,2]-, [3,3]- und [3,4]-sigmatropische Umlagerungen
Die Dienol-Benzol-Umlagerung von Propargylcyclohexadienolen: aromatische [1,2]-, [3,3]- und [3,4]-sigmatropische Umlagerungen
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Heimgartner, H., Zsindely, J., Hansen, H.-J., & Schmid, H. (1972). Die Dienol-Benzol-Umlagerung von Propargylcyclohexadienolen: aromatische [1,2]-, [3,3]- und [3,4]-sigmatropische Umlagerungen. Helvetica Chimica Acta, 55, 1113–1141. https://doi.org/10.1002/hlca.19720550408
Abstract
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Abstract
The acid catalysed dienol-benzene rearrangement of methyl substituted o- and p-propargylcyclohexadienols (18-22, 34 and35) was investigated. In the first step water is eliminated to yield the corresponding methyl propargyl benzonium ions (cf. scheme 6, a), which undergo [1s,2s] sigmatropic rearrangements to give propargylbenzenes (28, 29, 30, 38) and [3s,4s] sigmatropic rearrangements to give allenylbenzenes (24-27, 40) (cf. schemes 2, 3, 5, 6). [3s, 3s] sigmatropic rearrangements occur only to a small extend. In the rearrangement of
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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. (1972). Die Dienol-Benzol-Umlagerung von Propargylcyclohexadienolen: aromatische [1,2]-, [3,3]- und [3,4]-sigmatropische Umlagerungen. Helvetica Chimica Acta, 55, 1113–1141. https://doi.org/10.1002/hlca.19720550408
