Reaction of nitrosylpentaammineruthenium(II) with aromatic aldehydes in aqueous base. An example of catalyzed metal ion hydrolysis

Abstract

Evidence is presented that the reaction of [RU(NH,)~NO]~+ with several aromatic aldehydes in 0.1 M NaOH forms tran~-Ru(NH~)~(0H)N0~+ as the exclusive product, with the aldehyde serving as a catalyst. Electronic spectral data suggest that the reaction takes place via nucleophilic attack of the amido ligand trans to the nitrosyl group at the carbonyl of the aldehyde to form an unstable imine intermediate which hydrolyzes at the metal-nitrogen bond to yield the hydroxo product and quantitatively regenerate the aldehyde.

Identification of Pharmaceutical Impurities in Formulated Dosage Forms

“…[70][71][72] The presence of trace metal ions may lead to various drug degradation pathways. One example is metformin degradation catalyzed by a metal ion (M n + ) to form a drug degradation product as shown in Figure 9.…”

Reaction of nitrosylpentaammineruthenium(II) ion with organic carbonyls containing an .alpha.-methylene group: facile oxidative cleavage of a carbon-carbon bond

“…Previous studies have demonstrated that aldehydes and ketones with no a hydrogens undergo an entirely different (and much slower) reaction involving the ammonia ligand trans to the nitrosyl group. 18 The most apparent synthetic potential of reactions 1 and 2 is for oxidative ring opening and bifunctionalization of cyclic ketones under very mild conditions, thus representing an excellent alternative to present oxidative cleavage methods such as Marshall's19 cleavage of -diketone monothioketals or the known oxidative cleavage of cyclic olefins20 for the synthesis of macrocyclic compounds or compounds containing linear chains with fixed stereochemistry.…”