Mechanistic comparison of β-H elimination, β-OH elimination, and nucleophilic displacement reactions of β-hydroxy alkyl rhodium porphyrin complexes

Abstract

This article reports on kinetic studies for three alternate pathways, including β-hydrogen elimination, β-hydroxy elimination, and intramolecular nucleophilic displacement reactions, for rhodium porphyrin β-hydroxy alkyl reactions in water and DMSO to form ketone, alkene, and epoxide, respectively. Comparisons of activation parameters for these processes indicate that the β-hydroxy elimination process has the lowest activation enthalpy in water, but the intramolecular nucleophilic displacement pathway predominates in DMSO.