Journal of Organic Chemistry p. 1326 - 1333 (1981)
Update date:2022-08-03
Topics:
Billups, W. E.
Reed, Larry E.
Casserly, Edward W.
Lin, L. P.
Derivatives of bicyclo<4.1.0>heptatriene have been generated in solution by the base-induced dehydrochlorination of gem-dichlorocyclopropanes.Reaction of 7,7-dichlorodibenzobicyclo<4.1.0>heptane 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-Chlorodibenzobicyclo<4.1.0>heptane failed to reactwith potassium tert-butoxide in tetrahydrofuran.Generation of benzobicyclo<4.1.0>heptatrienes was also accomplished via the base-induced dehydrochlorination of gem-dichlorocyclopropanes. 1-Methylbenzobicyclo<4.1.0>heptatriene 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.
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