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Excursion to the World of Heptacyclic Compounds Made of Azulenes and Acetylenedicarboxylates
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Titel: |
Excursion to the World of Heptacyclic Compounds Made of Azulenes and Acetylenedicarboxylates |
In: | Helvetica Chimica Acta, 98, 2015, 7, S. 913-937 |
veröffentlicht: |
Wiley
|
Umfang: | 913-937 |
ISSN: |
0018-019X 1522-2675 |
DOI: | 10.1002/hlca.201500082 |
Zusammenfassung: | <jats:title>Abstract</jats:title><jats:p>Azulenes and acetylenedicarboxylates react under acid catalysis (<jats:italic>Brønsted</jats:italic> or <jats:italic>Lewis</jats:italic>) and form (2a<jats:italic>RS</jats:italic>,8a<jats:italic>SR</jats:italic>)‐2a,8a‐dihydrocyclopenta[<jats:italic>cd</jats:italic>]azulene‐1,2‐dicarboxylates as intermediate products, which then dimerize by central bond‐formation between C(2a<jats:sup>1</jats:sup>) and C(2′a<jats:sup>1</jats:sup>) 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[<jats:italic>cd</jats:italic>]azulene parts of the heptacyclic structures were also found.</jats:p> |
Format: | E-Article |
Quelle: | Wiley (CrossRef) |
Sprache: | Englisch |