33455-12-8Relevant academic research and scientific papers
Catalyst- A nd Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides
Afonin, Andrei V.,Gusarova, Nina K.,Ivanova, Nina I.,Khrapova, Kseniya O.,Larina, Lyudmila I.,Pavlov, Dmitry V.,Telezhkin, Anton A.,Trofimov, Boris A.,Volkov, Pavel A.
, p. 2224 - 2232 (2020)
Tertiary α-hydroxyphosphine oxides have been synthesized via the catalyst- A nd solvent-free reaction between available secondary phosphine oxides and aliphatic, aromatic and heteroaromatic ketones at 20-62? °C in near to 96-98percent yield. The developed method meets the requirements of green chemistry and the PASE (pot, atom, step economy) paradigm. According to quantum-chemical calculations at the B3LYP/6-311++G(d,p) level, the synthesized hydroxyphosphine oxides feature a weak (≈3 kcal·mol -1) O-H···O=P intramolecular hydrogen bond.
The reaction activity of aromatic carbonyl compounds with diphenylphosphine oxide studied by 31P NMR
Zheng, Jinyun,Feng, Xiangming,Yu, Yujian,Zhen, Xiaomin,Zhao, Yufen
, p. 1080 - 1087 (2013/09/02)
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.
