✦ LIBER ✦

Die Thermolyse von 2,2,6,7-Tetramethyl-1,7 -epidioxybicyclo[4.3.0]non-8-en

✍ Scribed by Werner Skorianetz; Günther Ohloff

Publisher: John Wiley and Sons
Year: 1976
Tongue: German
Weight: 753 KB
Volume: 59
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19760590102

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✦ Synopsis

Thermolysis of 2,2,6,7‐Tetramethyl‐1,7‐epidioxybicyclo[4.3.0]non‐8‐ene.

Dye‐sensitized photooxygenation of the cyclopentadiene derivative 1 gives three products: the peroxide 2a and the monocyclic ketones 5 and 8. 5 and 8 are probably formed by rearrangement of the unstable peroxide 2b. Thermolysis of 2a gives, besides 5 and 8, the furylketone 9 and the cyclooctenone derivative 10. The structures of the new compounds have been established by means of spectroscopic methods and chemical transformations. A reaction mechanism for the formation of 5, 8, 9 and 10 from 2a is proposed. Irradiation of 10 leads to the two diastereoisomeric trans cyclooctenones 12a and 12b.

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