Organophosphorus Compounds. II. Preparation of Phosphonic Acid Esters using the Dicyclohexylcarbodiimide Reagent

1963 ◽  
Vol 16 (4) ◽  
pp. 609 ◽  
Author(s):  
JA Maynard ◽  
JM Swan
Keyword(s):  
Phosphonic Acid ◽  
Organophosphorus Compounds ◽  
Phosphonic Acids ◽  
Pyridine Solution ◽  
Acid Esters

Mono- and diesters of phosphonic acids are conveniently prepared by reaction of a phosphonic acid with appropriate quantities of NN'-dicyclohexylcarbodiimide and an alcohol or phenol in pyridine solution.

Reaktionen polyhalogenierter Cyclobutene mit Trimethylphosphit /Reactions of Polyhalogenated Cyclobutenes with Trimethylphosphite

1979 ◽  
Vol 34 (9) ◽  
pp. 1252-1259 ◽  
Author(s):  
Gert Bauer ◽  
Gerhard Hagele
Keyword(s):  
Phosphonic Acid ◽  
Organophosphorus Compounds ◽  
Trimethyl Phosphite ◽  
Substitution Reactions ◽  
Acid Esters

Abstract Structure and reactive behaviour of polyhalogenated cyclobutenes towards trimethyl phosphite are studied in detail. Stable phosphoranes RP(F)(OCH3)3 as intermediates of Arbuzov-type reactions are obtained. Controlled decomposition of phosphoranes leads to highly reactive cyclobutenyl substituted phosphonic acid esters RP(O)(OCH3)2. Substitution reactions at aliphatic and vinylic positions of RP(O)(OCH3)2 are observed. Biphosphonic acid esters R[P(O)(OCH3)2]2 are synthesized. Some routes to perhalogenated cyclobutenes are described. NMR and MS data for the hitherto unknown cyclobutenyl-substituted organophosphorus compounds are given.

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 Straightforward Immobilization of Phosphonic Acids and Phosphoric Acid Esters on Mesoporous Silica and Their Application in an Asymmetric Aldol Reaction

Nanomaterials ◽  
2019 ◽  
Vol 9 (2) ◽  
pp. 249 ◽  
Author(s):  
Christian Weinberger ◽  
Tatjana Heckel ◽  
Patrick Schnippering ◽  
Markus Schmitz ◽  
Anpeng Guo ◽  
...  
Keyword(s):  
Mesoporous Silica ◽  
Phosphoric Acid ◽  
Surface Area ◽  
Aldol Reaction ◽  
Synthesis Method ◽  
Mesoporous Silicas ◽  
Phosphonic Acids ◽  
Asymmetric Aldol ◽  
Asymmetric Aldol Reaction ◽  
Acid Esters

The combined benefits of moisture-stable phosphonic acids and mesoporous silica materials (SBA-15 and MCM-41) as large-surface-area solid supports offer new opportunities for several applications, such as catalysis or drug delivery. We present a comprehensive study of a straightforward synthesis method via direct immobilization of several phosphonic acids and phosphoric acid esters on various mesoporous silicas in a Dean–Stark apparatus with toluene as the solvent. Due to the utilization of azeotropic distillation, there was no need to dry phosphonic acids, phosphoric acid esters, solvents, or silicas prior to synthesis. In addition to modeling phosphonic acids, immobilization of the important biomolecule adenosine monophosphate (AMP) on the porous supports was also investigated. Due to the high surface area of the mesoporous silicas, a possible catalytic application based on immobilization of an organocatalyst for an asymmetric aldol reaction is discussed.

PHOSPHONIC ACID MONOLAYERS FOR CORROSION PROTECTION OF COPPER: EQCM AND EIS INVESTIGATIONS

2019 ◽  
Vol 27 (06) ◽  
pp. 1950166
Author(s):  
AYSEL YURT ◽  
ESRA SOLMAZ
Keyword(s):  
Molecular Structure ◽  
Corrosion Protection ◽  
Phosphonic Acid ◽  
Quantum Chemical ◽  
Electrochemical Impedance ◽  
Film Formation ◽  
Copper Surface ◽  
Chemical Mechanism ◽  
Frequency Change ◽  
Phosphonic Acids

Preparation, characterization and application of protective phosphonic acid monolayers formed by 1-Aminohexyl phosphonic acid (AHP), 1,4-butanediphosphonic acid (BDPA), 1-amino-1,3-dimethylbutyl phosphonic acid (ADBP) on copper surface as anticorrosive self-assembled molecular monolayers (SAMs) have been investigated by atomic force microscopy (AFM) analysis, electrochemical impedance spectroscopy (EIS) and in situ electrochemical quartz crystal microbalance (EQCM) techniques. Film formation and growth were monitored by EQCM and the step-by-step construction of monolayer was investigated through measurement of the frequency change, which corresponds to mass change due to the adsorption of molecules. Observed increase in electrode mass suggests that SAMs formed on copper surface by the adsorption of phosphonic acids. Results clearly demonstrate that adsorbed amounts of phosphonic acids were strongly influenced by immersion time and molecular structure. Quantum chemical calculations were performed by semi-empirical PM6 method, in order to explain the relationship between molecular structure and adsorption mechanism. Quantum chemical parameters of phosphonic acids propound that adsorption of molecules on copper surface has a chemical mechanism. Corrosion protection ability of SAMs against the acidic corrosion of copper has been evaluated in 0.1[Formula: see text]M H2SO4 solution. It was found that phosphonic acid SAMs act as protective barrier and the protection efficiencies increased in the following order: [Formula: see text].

scholarly journals Protolysis and Complex Formation of Organophosphorus Compounds—Characterization by NMR-Controlled Titrations

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3238 ◽  
Author(s):  
Hägele
Keyword(s):  
Dissociation Constants ◽  
Organophosphorus Compounds ◽  
Chemical Shifts ◽  
2D Nmr ◽  
Coupling Constants ◽  
Phosphonic Acids ◽  
Specific Chemical ◽  
Hyphenated Technique ◽  
Aminophosphonic Acids ◽  
2D Nmr Spectra

Phosphonic acids, aminophosphonic acids, and phosphonocarboxylic acids are characterized by an advanced hyphenated technique, combining potentiometric titration with NMR spectroscopy. Automated measurements involving 13C, 19F and 31P nuclei lead to “pseudo 2D NMR” spectra, where chemical shifts or coupling constants are correlated with analytical parameters. Dissociation constants, stability constants, dynamic and specific chemical shifts are determined. Macroscopic and microscopic dissociation equilibria are discussed.

Novel Fluorescent Phosphonic Acid Esters for Discrimination of Lipases and Esterases

ChemBioChem ◽  
2005 ◽  
Vol 6 (10) ◽  
pp. 1776-1781 ◽  
Author(s):  
Hannes Schmidinger ◽  
Ruth Birner-Gruenberger ◽  
Gernot Riesenhuber ◽  
Robert Saf ◽  
Heidrun Susani-Etzerodt ◽  
...  
Keyword(s):  
Phosphonic Acid ◽  
Acid Esters
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