UZH-Logo

Maintenance Infos

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.

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.

Citations

22 citations in Web of Science®
2 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

0 downloads since deposited on 29 Dec 2014
0 downloads since 12 months

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:05 Apr 2016 18:39
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds
Publisher DOI:https://doi.org/10.1002/hlca.19700530540
Permanent URL: https://doi.org/10.5167/uzh-102600

Download

[img]
Content: Published Version
Filetype: PDF - Registered users only
Size: 214kB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations