Simple hydroboration of a cyclopropane ring is not a reaction that is easily carried out. Attempts to hydroborate the three membered ring of quadricyciane, however are encouraged by the high strain energy (96 kcal/mol) of this tetracyclic system. Observation of nortricyclanol product would be taken as a sign of a successful oxidative hydroboration of quadricyciane. Some minor successes in earlier hydroborations of quadricyciane with a Rh (I) reagent, Wilkinson's catalyst, encouraged us. Wilkinson's catalyst was however better at inducing isomerization to norbornadiene than hydroboration of quadricyciane. The main focus of our research is the hydroboration of quadricyciane using RhCl3 since this rhodium reagent was very effective in promoting hydroboration of alkenes. Using RhCl3 we carried out this reaction under various conditions and we were unable to produce nortricyclanol. We have studied the ability of RhCl3 to isomerize quadricyciane to norbornadiene and as expected, the ease of this reaction suggests a the reason why nortricyclanol is not produced.
Library of Congress Subject Headings
Hydroboration; Rhodium catalysts; Isomerization; Hydrocarbons
Department, Program, or Center
School of Chemistry and Materials Science (COS)
DiDonato, Dana, "The Effect of rhodium reagents upon the hydroboration and thermal isomerization of quadricyclane" (2001). Thesis. Rochester Institute of Technology. Accessed from
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