Abstract
The flow-vacuum pyrolyses of 5-methylene-5 H-dibenzo[ a, d]cycloheptene ( 11) were studied by GC/MS at 1.33 mbar and temperatures between 750 and 1050 °C. The major reaction products: anthracene, phenanthrene, 1-phenylnaptalene and 2-phenylnaphtalene were accompanied by small amounts of 9-methylanthracene, 9,10-dimethylanthracene and fluoranthene. This product distribution differs from that of related—partially hydrogenated—analogs of 11 (which are fully converted at about 850 °C). A reaction mechanism for pyrolysis of 11 is suggested, including more parallel routes and involving carbenic- and diradical transformations of the type recently observed during high-temperatures pyrolyses of related polycyclic aromatic hydrocarbons.
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