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Die Dienol-Benzol-Umlagerung von Propargylcyclohexadienolen: aromatische [1,2]-, [3,3]- und [3,4]-sigmatropische Umlagerungen


Heimgartner, Heinz; Zsindely, Janos; Hansen, Hans-Jürgen; Schmid, Hans (1972). Die Dienol-Benzol-Umlagerung von Propargylcyclohexadienolen: aromatische [1,2]-, [3,3]- und [3,4]-sigmatropische Umlagerungen. Helvetica Chimica Acta, 55(4):1113-1141.

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 2-propargyl-2,4,6- trimethylcyclohexa-3,5-dien-1-ol (18) a [1s,2s] sigmatropic methyl shift is observed (4%).

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 2-propargyl-2,4,6- trimethylcyclohexa-3,5-dien-1-ol (18) a [1s,2s] sigmatropic methyl shift is observed (4%).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1972
Deposited On:29 Dec 2014 15:09
Last Modified:05 Apr 2016 18:39
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds
Publisher DOI:https://doi.org/10.1002/hlca.19720550408

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