Abstract
Abstract1‐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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