Date of Award
Master of Science (MS)
Robert L. Dressler
The principal objective of the present study involved an attempt to induce prototropic shifts in the 4,5- dibenzenesulfonimidoindan molecule, using acidic and basic catalysts. The prototropic rearrangement by which 4,5-dibenzenesulfonimidoindan would be converted to 4,5-dibenzenesulfonamidoindene has been largely unsuccessful. However, some possibility of proton rearrangement was observed when using perchloric acid as a catalyst. Reaction of 4,5-dibenzenesulfonimidoindan with hydrobromic acid gave a product containing bromine, indicating that addition of the reagent rather than rearrangement had occurred. Prototropic shifts of 4,5-dibenzenesulfonimidoindan in pyridine , initiated by abstraction of an allylic proton, also proved unsuccessful. Even though proton rearrangement was unsuccessful, ten new organic compounds were synthesized and most of the physical properties and spectra were reported.
Copyright 1977 Jong Ho Kim
Kim, Jong Ho, "The Attempted Prototropic Shifts of 4, 5-Dibenzenesulfonimidoindan." (1977). Master's Theses. 1668.