Cycloallenes, 11. 1‐Phenyl‐1,2‐cyclononadiene: Preparation and Dimerisation

1-Phenyl-1,2-cyclononadiene (10) was prepared by addition of dibromocarbene to 1-phenylcyclooctene and treatment of the resulting 9,9-dibromobicyclo[6.1.0]nonane 7 with methyllithium. In addition to 10, the 9-bromo-9-methylbicyclononanes cis- and trans-8 as well as the bicyclopropylidene 9 were formed. The dimerisation of 10 proceeded slowly already at room temperature and gave rise to the 1,2-bismethylenecyclobutane derivatives cis- and trans-11. From the complex mixture that resulted on thermolysis at 200°C of cis- and trans-11 only their isomer 12 could be isolated. Heating of a benzene solution of tetracyanoethylene and cis- and trans-11 afforded the Diels-Alder adduct 13 of cis-11, which rearranged to the benzodicyclononene derivative 14 on thermolysis.

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