Benzonorbomadiene oxide

Another modified metal hydride, lithium triethylborohydride, the so-called superhydride , has been introduced as a powerful reducing agent especially suitable for trisubstituted, tetrasubstituted and bicy-clic epoxides (Table 3). With trisubstituted epoxides the regiochemistry is completely controlled to give only tertiary alcohols. No skeletal rearrangement is observed for benzonorbomadiene oxide. 

To overcome these obstacles, we turned our attention to novel approaches to benzazepine 6 that did not involve benzonorbomadiene and obviated the problems presented by cyclopentadiene generation and oxidative cleavage chemistry (Figure 3.8). Both the Mazzocchi and discovery syntheses generated 1,3-indane dicarbonyl intermediates that were converted to the bicyclic aryl piperidine nucleus. We therefore focused on alternative indane syntheses to access this functionality, targeting readily available synthetic precursors. 

Norbomene has also been utilized in a one-step construction of C2-symmetrical pallada(IV)spirocycle complexes featuring one palladium(IV)-Csp bond and one palladium(IV)-0 bond in each palladacyclic ring (Scheme 14) [24]. Oxidative cyclization of norbomene or benzonorbomadiene with chloranil and Pd2(dba)3 (dba = dibenzylideneacetone) afforded new palladium(IV) complexes bearing various Lewis basic ligands (L = pyridine, THF, and diethyl ether). Selected complexes were characterized by X-ray crystallography. Notably, these palladium (IV) complexes proved to be stable for prolonged periods of time at room temperature, both in the solid state and in solution. The complexes decomposed upon... 

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