Toward hydrogen bonds of predictable geometry

• Main Author: Hsu, Robert Shao-chih
• Format: Others
• Published: BYU ScholarsArchive 1972
• Subjects: Hydrogen bonding
• Online Access: https://scholarsarchive.byu.edu/etd/8233; https://scholarsarchive.byu.edu/cgi/viewcontent.cgi?article=9233&context=etd

A literature review on the geometry of hydrogen bonding showed that the geometry is often de-emphasized or even ignored, probably because of the inherent flexibility of many systems studied. Examination of molecular models suggested the geometrically constrained bicyclo [2, 2, 1] heptane system wherein hydrogen bond distances and angles might be more easily predicted. Dihydroboration-oxidation of norbornadiene was shown to yield exo, exo-2,5-norbornadiol, thus clarifying uncertainties in the literature. 2, 5-Norbornadiol was oxidized to the corresponding dione, heretofore inadequately characterized. Several derivatives of the dione were prepared, and spectral data were accumulated for the dione, its precursor, and its derivatives. The mono(ethylene ketal) of 2,5-norbornadione was prepared as a key intermediate in projected synthesis schemes. Preliminary work was initiated in converting it to compounds of interest. Although norbornadione was prepared by dihydroboration followed directly with oxidation, the yields were low under all conditions tried. Consequently, a two-step sequence was used.