Preparation and characterization of 2-silanorbornanes

Article abstract of DOI:10.1021/jo00348a004

Four members of the new class of 2-silabicyclo<2.2.1>heptanes, or 2-silanorbornanes, were prepared: 2-silanorbornane (1), 2,2-dichloro-2-silanorbornane (2), 2-chloro-2-methyl-2-silanorbornane (3), and 2-methyl-2-silanorbornane (4); the ring-closure reaction involved a platinum-catalyzed, intramolecular hydrosilation.The silanes were chracterized by carbon and hydrogen elemental analyses and by 1H, 13C, and 29Si NMR, IR, and mass spectrometry.Isomer assigments for 3 and 4 were made on the basis of the NMR data.In the mass spectra, each compound gave an abundant molecular ion and a major mode of fragmentation peculiar to this bicyclic system.Some initial stereochemical studies of the reactions of 3 and 4 were performed, including fluoride-induced equilibration of the isomers of 4.