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Thermisches Verhalten von Mesitylallenen; Beispiel einer aromatischen [1,5s]-sigmatropischen H-Verschiebung


Heimgartner, Heinz; Zsindely, Janos; Hansen, Hans-Jürgen; Schmid, Hans (1970). Thermisches Verhalten von Mesitylallenen; Beispiel einer aromatischen [1,5s]-sigmatropischen H-Verschiebung. Helvetica Chimica Acta, 53(5):1212-1215.

Abstract

Mesitylallene (6a), 1-mesityl-3-methyl-allene (6b) and 1-mesityl-3,3-dimethyl- allene (6c) were prepared via dienol-benzene-rearrangements. At 170° 6a isomerises to give 5,7-dimethyl-1,2-dihydronaphthalene (8). Under the same conditions 6b rearranges to give 2,5,7-trimethyl-1,2-dihydronaphthalene (10; 60%) and cis-1-mesitylbuta-1,3-diene (11; 40%) while 6c gives only cis-1-mesityl-3-methyl-buta-1,3-diene (13). The allenes undergo first an aromatic [1,5s]-sigmatropic H-shift to the o-xylylene derivatives 7, 9 and 12, which then exhibit disrotatory ring closure to the dihydronaphthalenes or aromatic [1,7a]-sigmatropic H-shift to the 1-mesitylbuta-1,3-dienes.

Abstract

Mesitylallene (6a), 1-mesityl-3-methyl-allene (6b) and 1-mesityl-3,3-dimethyl- allene (6c) were prepared via dienol-benzene-rearrangements. At 170° 6a isomerises to give 5,7-dimethyl-1,2-dihydronaphthalene (8). Under the same conditions 6b rearranges to give 2,5,7-trimethyl-1,2-dihydronaphthalene (10; 60%) and cis-1-mesitylbuta-1,3-diene (11; 40%) while 6c gives only cis-1-mesityl-3-methyl-buta-1,3-diene (13). The allenes undergo first an aromatic [1,5s]-sigmatropic H-shift to the o-xylylene derivatives 7, 9 and 12, which then exhibit disrotatory ring closure to the dihydronaphthalenes or aromatic [1,7a]-sigmatropic H-shift to the 1-mesitylbuta-1,3-dienes.

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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:1970
Deposited On:29 Dec 2014 15:06
Last Modified:21 Nov 2017 17:36
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds
Publisher DOI:https://doi.org/10.1002/hlca.19700530540

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