¹³C Kinetic Isotope Effect of the Pudovik Reaction

Abstract

¹³C kinetic isotope effect (KIE) was determined by means of ¹³C NMR for the carbonyl atom in 2-nitrobenzaldehyde in its reaction with 2H-2-oxo-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane in acetonitrile at 25°C. The observed isotope effect k₁₂/k₁₃ = 1.0238 ± 0.0031 evidences that the formation of the P‒C bond in the Pudovik reaction catalyzed by triethylamine is less advanced than the π-bond breakage of the aldehyde carbonyl group.

GRAPHICAL ABSTRACT

Keywords:

• Pudovik reaction
• kinetic isotope effects
• reaction mechanism
• NMR spectroscopy

ACKNOWLEDGMENT

This work was supported by the Ministry of Science and Higher Education (Grant 3 T09A 115 28) and Lodz University of Technology (Grant DS/I18/2014).