75949-02-9Relevant academic research and scientific papers
Generation of Bicycloheptatrienes
Billups, W. E.,Reed, Larry E.,Casserly, Edward W.,Lin, L. P.
, p. 1326 - 1333 (2007/10/02)
Derivatives of bicycloheptatriene have been generated in solution by the base-induced dehydrochlorination of gem-dichlorocyclopropanes.Reaction of 7,7-dichlorodibenzobicycloheptane with potassium tert-butoxide in tetrahydrofuran at 0 deg C gives mainly products derived from solvent incorporation by carbene insertion.Evidence that the carbene results from rearrangement of the bicycloheptatriene derives from the successful interception of the bicycloheptatriene with nucleophile (MeS-). endo-7-Chlorodibenzobicycloheptane failed to reactwith potassium tert-butoxide in tetrahydrofuran.Generation of benzobicycloheptatrienes was also accomplished via the base-induced dehydrochlorination of gem-dichlorocyclopropanes. 1-Methylbenzobicycloheptatriene gives products derived from multiple carbene-carbene rearrangements.In contrast, nonannelated methylbicycloheptatrienes generated by the dehydrochlorination route give only carbene-derived products resulting from the initially produced bicycloheptatriene.
