Carbon-13 NMR and IR Spectroscopic Studies on Some 7-Oxabicycloheptanes and -heptenes. n-? Interaction and Hydrogen Bonding

Article abstract of DOI:10.1246/bcsj.60.613

The 13C NMR spectra of diastereomeric pairs of the title compounds together with some tetrahydrofurans were examined and the chemical shifts were compared with those for the corresponding bicyclo<2.2.1>heptanes and -heptenes.The intramolecular interaction between the n-orbital of an oxygen atom and the ?-orbital of an olefinic bond was found in 2-methylene-7-oxabicyclo<2.2.1>heptane.Intramolecular hydrogen bonding between the 7-oxygen and the hydroxyl group occurs in exo-7-oxabicyclo<2.2.1>heptane-2-methanol.