The Reaction Activity of Aromatic Carbonyl Compounds with Diphenylphosphine Oxide Studied by ³¹P NMR

Abstract

A series of α-hydroxyphosphine oxides were prepared by the reactions of diphenylphosphine oxide and aromatic carbonyl compounds and characterized by ¹H NMR, ¹³C NMR, ³¹P NMR, FT-IR, ESI-MS, and HR-MS spectra. The reaction rates and experimental conditions of aromatic aldehydes and aromatic ketones were obviously different due to the activity of their carbonyls. The different substituents of the aromatic aldehydes affected the reaction rate too, and the quantitative reactivity of their substituent conformed to the Hammett equation. The results were confirmed by ³¹P NMR spectroscopy.

GRAPHICAL ABSTRACT

Keywords:

• Diphenylphosphine oxide
• aromatic aldehyde
• Hammett's plot
• ³¹P NMR tracking

Acknowledgments

The authors would like to thank the National Natural Science Foundation Committee of China for financial support to this work (No. 20732004).