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Excursion to the World of Heptacyclic Compounds Made of Azulenes and Acetylenedicarboxylates


Chen, Yi; Lehto, Erja; Uebelhart, Peter; Linden, Anthony; Hansen, Hans-Jürgen (2015). Excursion to the World of Heptacyclic Compounds Made of Azulenes and Acetylenedicarboxylates. Helvetica Chimica Acta, 98(7):913-937.

Abstract

Azulenes and acetylenedicarboxylates react under acid catalysis (Brønsted or Lewis) and form (2aRS,8aSR)-2a,8a-dihydrocyclopenta[cd]azulene-1,2-dicarboxylates as intermediate products, which then dimerize by central bond-formation between C(2a1) and C(2’a1) and various peripheral C,C’-atoms of the dihydroazulene fragments, depending on the substituents present. The reactions are often accompanied by the formation of side-products, such as 2-(azulen-1-yl)fumarates and -maleates and others caused by H-shifts of the primary intermediates. H-Shifts between the two tetrahydrocyclopenta[ cd]azulene parts of the heptacyclic structures were also found.

Abstract

Azulenes and acetylenedicarboxylates react under acid catalysis (Brønsted or Lewis) and form (2aRS,8aSR)-2a,8a-dihydrocyclopenta[cd]azulene-1,2-dicarboxylates as intermediate products, which then dimerize by central bond-formation between C(2a1) and C(2’a1) and various peripheral C,C’-atoms of the dihydroazulene fragments, depending on the substituents present. The reactions are often accompanied by the formation of side-products, such as 2-(azulen-1-yl)fumarates and -maleates and others caused by H-shifts of the primary intermediates. H-Shifts between the two tetrahydrocyclopenta[ cd]azulene parts of the heptacyclic structures were also found.

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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:English
Date:2015
Deposited On:12 Nov 2015 07:19
Last Modified:05 Apr 2016 19:30
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Swiss National Science Foundation
Publisher DOI:https://doi.org/10.1002/hlca.201500082

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