Phosphonic acids and esters. XIX. Synthesis of substituted phenyl- and arylphosphonates by the photoinitiated arylation of trialkyl phosphites

1968 ◽  
Vol 33 (2) ◽  
pp. 632-636 ◽  
Author(s):  
Richard Obrycki ◽  
Claibourne E. Griffin
Keyword(s):  
Phosphonic Acids ◽  
Trialkyl Phosphites

Synthesis of 1-Hydroxypyrrolidin-2,5-dione Derivatives of the Phosphonic - Hydroxamic Acid Antibiotic SF-2312

2006 ◽  
Vol 59 (4) ◽  
pp. 283 ◽  
Author(s):  
Wamuyu Owotoki ◽  
Detlef Geffken ◽  
Thomas Kurz
Keyword(s):  
Hydroxamic Acid ◽  
Phosphonic Acids ◽  
Trialkyl Phosphites ◽  
Derivatives Of ◽  
Substituted 1 ◽  
Ring Position

Analogues of the antibiotic SF-2312 with a 3-substituted 1-hydroxypyrrolidine moiety have been prepared from 1-benzyloxy-3-bromopyrrolidin-2,5-dione (1) through Michaelis–Arbusov reaction with various trialkyl phosphites and subsequent alkylation of ring position 3. Cleavage of phosphonic esters 3 by TMSBr afforded the corresponding phosphonic acids 7, which were treated with ethanolamine to give the monosalts 8. Finally, hydrogenolysis furnished 1-hydroxypyrrolidin-2,5-diones 9.

scholarly journals Microwaves as “Co-Catalysts” or as Substitute for Catalysts in Organophosphorus Chemistry

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1196
Author(s):  
György Keglevich
Keyword(s):  
Coupling Reaction ◽  
Diels Alder ◽  
Typical Case ◽  
Conventional Heating ◽  
Phosphine Oxides ◽  
Phosphonic Acids ◽  
Co Catalysts ◽  
Mw Irradiation ◽  
Organophosphorus Chemistry ◽  
Hydrolysis Of

The purpose of this review is to summarize the importance of microwave (MW) irradiation as a kind of catalyst in organophosphorus chemistry. Slow or reluctant reactions, such as the Diels-Alder cycloaddition or an inverse-Wittig type reaction, may be performed efficiently under MW irradiation. The direct esterification of phosphinic and phosphonic acids, which is practically impossible on conventional heating, may be realized under MW conditions. Ionic liquid additives may promote further esterifications. The opposite reaction, the hydrolysis of P-esters, has also relevance among the MW-assisted transformations. A typical case is when the catalysts are substituted by MWs, which is exemplified by the reduction of phosphine oxides, and by the Kabachnik–Fields condensation affording α-aminophosphonic derivatives. Finally, the Hirao P–C coupling reaction may serve as an example, when the catalyst may be simplified under MW conditions. All of the examples discussed fulfill the expectations of green chemistry.

scholarly journals A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

Organics ◽  
2021 ◽  
Vol 2 (2) ◽  
pp. 107-117
Author(s):  
Mattia Forchetta ◽  
Valeria Conte ◽  
Giulia Fiorani ◽  
Pierluca Galloni ◽  
Federica Sabuzi
Keyword(s):  
Metal Oxides ◽  
Phosphonic Acid ◽  
Organic Molecules ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Phosphonic Acids ◽  
Sustainable Improvement ◽  
Phosphonate Esters ◽  
First Time ◽  
Complex Organic

Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

scholarly journals α-(Imino)pyridyldifluoroethyl Phosphonates: Novel Promising Building Blocks in Synthesis of Biorelevant Aminophosphonic Acids Derivatives

Organics ◽  
2021 ◽  
Vol 2 (2) ◽  
pp. 72-83
Author(s):  
Oksana M. Shavrina ◽  
Lyudmyla V. Bezgubenko ◽  
Andrii V. Bezdudny ◽  
Petro P. Onys’ko ◽  
Yuliya V. Rassukana
Keyword(s):  
Carbon Atom ◽  
Building Blocks ◽  
Synthetic Approach ◽  
Phosphonic Acids ◽  
Aminophosphonic Acids ◽  
Convenient Synthetic Approach

A convenient synthetic approach to previously unknown NH-iminophosphonates bearing 2-, 3-, and 4-pyridyldifluoromethyl groups at the imine carbon atom was developed. The synthetic potential of these novel building blocks was demonstrated by their conversion into highly functionalized acyclic and heterocyclic aminophosphonates and phosphonic acids combining in their structure biorelevant aminophosphonic fragment, difluoromethyl group, and pyridyl, piperidyl, thiazolidin-4-one, or thiazidinan-4-one heterocyclic moieties in a single molecular platform.

scholarly journals Combined Experimental and Theoretical Insights into the Corrosion Inhibition Activity on Carbon Steel Iron of Phosphonic Acids

Molecules ◽  
2020 ◽  
Vol 26 (1) ◽  
pp. 135
Author(s):  
Aurelia Visa ◽  
Nicoleta Plesu ◽  
Bianca Maranescu ◽  
Gheorghe Ilia ◽  
Ana Borota ◽  
...  
Keyword(s):  
Carbon Steel ◽  
Corrosion Inhibition ◽  
Density Functional ◽  
Energy Gap ◽  
Electrochemical Impedance ◽  
Charge Transfer Resistance ◽  
Phosphonic Acids ◽  
Transfer Resistance ◽  
Potential Map ◽  
Chlorine Ions

The inhibition effect of N,N′-phosphonomethylglycine (PMG) and vinyl phosphonic acid (VPA) on the 3% NaCl acidic solution corrosion of carbon steel iron was studied at different immersion times by potentiodynamic polarization, electrochemical impedance spectroscopy, attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy, and computational methods. It is found from the polarization studies that PMG and VPA behave as mixed-type inhibitors in NaCl. Values of charge transfer resistance (Rct) and double layer capacitance (Cdl) in the absence and presence of inhibitors are determined. The PMG and VPA inhibitors were capable of inhibiting the corrosion process up to ≈91% and ≈85%, respectively. In the presence of PMG, the synergic effect of chlorine ions was observed. Density functional theory (DFT) was engaged to establish the adsorption site of PMG, VPA, and their deprotonated states. For studied compounds, the resulted values of ELUMO, EHOMO, energy gap (∆E), dipole moment (μ), electronic hardness (η), global softness (σ), electrophilic index (ω), and the electronic potential map are in concordance with the experimental data results regarding their corrosion inhibition behavior and adsorption on the metal surface.

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