Ionic Hydrogenation of Pyridinium and Azetidinium Cations

Research described herein seeks to study the reactivity of CpRu(P-P)H with pyridinium and azetidinium cations. For the former, we wish to determine if a previously established methodology for the regioselective reduction of a particular pyridinium cation may be extended to other pyridinium cations and if the methodology may be improved with the introduction of a pendant amine in the diphosphine. Our studies have shown that this methodology could not be extended to pyridinium cations having substituents on the pyridinium ring. For the latter, we seek to establish the reactivity of CpRu(P-P)H with azetidinium cations and compare these results to what the Norton Group has previously established in studies concerning aziridinium cations. Our studies have shown that opening of azetidinium is about six orders of magnitude slower compared to the opening of aziridinium.