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The 18-electron electrocyclisation of vinylogous fidecene. an unusual sequence of pericyclic processes

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
23
Issue
24
Identifiers
DOI: 10.1016/s0040-4039(00)87360-8

Abstract

Abstract Upon thermal activation the vinylogous fidecene 1 is isomerised into the pentacyclic indenoid hydrocarbon 13 (benzene, t 1 2 (150°C) ca. 5 min), the formation of which is explained by an initial conrotatory (“symmetry-forbidden”) 18-electron electrocyclisation followed by two fast hydrogen migrations ([1.9], [1.5]) and 14π-electrocyclisation.

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