42366-52-9Relevant academic research and scientific papers
Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds
Li, Chunya,Wang, Qi,Zhang, Jian-Qiu,Ye, Jingjing,Xie, Ju,Xu, Qing,Han, Li-Biao
supporting information, p. 2916 - 2922 (2019/06/18)
Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.
The reactivity of arylphosphine oxides under Bouveault-Blanc reaction conditions
Korzeniowska, Ewelina,Kozio?, Anna E.,?astawiecka, El?bieta,Flis, Anna,Stankevi?, Marek
, p. 5153 - 5162 (2017/07/28)
Treatment of tertiary arylphosphine oxides with alkali metal/alcohol reagent system lead to the corresponding cyclohexyl-substituted phosphine oxides. This transformation makes use of the inexpensive sodium as the electron donor and an alcohol as the proton source, and provides an attractive alternative to reactions mediated by expensive transition metals. Under optimized conditions numerous mono- and diaryl substituted phosphine oxides were transformed into the corresponding mono- and dicyclohexyl-substituted phosphine oxides in good yields. Furthermore, the formation of 1,2-bis(phosphinoyl)cyclohexanes or unknown 5,10-dialkyltetradecahydrophosphanthrene 5,10-dioxides as side products was observed, which are hardly accessible by other procedures.
