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Trimethyl or triethyl phosphite in the Arbuzov reaction with 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-one or analogous 6-bromomethyl-3,4-dihydropyridin-2(1H)-one provided the respective 6-alkylphosphonates in excellent yields. The heterocyclic alkylphosphonates are useful synthons in the Horner–Wadsworth–Emmons reaction for introducing a styryl moiety. Bromination of 6-methyl-4-phenyl-3,4-dihydropyridin-2(1H)-one with NBS in methanol resulted in an unexpected compound, while bromination in chloroform with bromine yielded the expected 6-bromomethyl-3,4-dihydropyridin-2(1H)-one, which undergoes facile nucleophilic substitutions. The intermediates and products are validated by single crystal X-ray diffraction. [ABSTRACT FROM AUTHOR]

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.

Five- and six-membered cyclic nitroxide-based allylic phosphonate esters, α-ketophosphonate esters were obtained from the corresponding paramagnetic allyl bromides and acyl chlorides respectively via the Arbuzov reactions. The α-hydroxyphosphonate esters were accessed by Pudovik reactions from the corresponding paramagnetic ketones and aldehydes. The β-ketophosphonate esters were obtained from the appropriate 1-alkynylphosphonate esters via PdCl2-catalyzed hydration. The synthesis of an allylic phosphate ester and a paramagnetic geminal bisphosphonate was also reported. [ABSTRACT FROM AUTHOR]

A new method for C–N bond transformations into C–P bonds was developed using 1,2,3-triazoles as leaving groups in SNAr–Arbuzov reactions. A series of C6-phosphonated 2-triazolylpurine derivatives was synthesized for the first time, with the isolated yields reaching up to 82% in the C–P-bond-forming event. The SNAr–Arbuzov reaction of 2,6-bistriazolylpurines follows the general regioselectivity pattern of the C6-position being more reactive towards substitution, which was unambiguously proved by X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl)phosphonate.

Five- and six-membered cyclic nitroxides containing α-ketophosphonates were obtained from the corresponding paramagnetic acyl chlorides via the Arbuzov reaction, while those containing β-ketophosphonates were obtained from the appropriate 1-alkynylphosphonates via PdCl2-catalyzed hydration. These new paramagnetic phosphorus compounds proved to be useful reagents in C–C and C=C bond-forming reactions and in functional group transformation reactions, namely, reduction, phospha-Brook rearrangement, and Regitz diazo transfer reactions. The synthesis of a paramagnetic geminal bisphosphonate was also reported. [ABSTRACT FROM AUTHOR]

A convenient procedure for the preparation of (trimethylsilyl)dimethylphosphinite was developed. The synthetic potential of the latter was exemplified by the preparation of dimethylphosphinoyl-derived nitriles, amines, acetone, acetic and acetoacetic acids as valuable building blocks for medicinal and materials chemistry. [ABSTRACT FROM AUTHOR]

Chrysin is a widely distributed natural flavonoid with broad biological activities, but its poor bioavailability and insufficient efficacy limit its clinical applications. Based on prodrug and combination principles, we designed and synthesized sixteen new chrysin derivatives containing phosphonate, phosphoramidate and primary amine groups with different spaces at C‐7 position of chrysin in 66–93 % yields. The synthetic strategies involve the use of classic Arbuzov, Staudinger‐phosphite and Staudinger‐reduction reactions. The derivatives were herein prepared from easily available starting materials under mild conditions and fully characterized by 1H/13C/31P NMR, IR, MS, elemental analysis or HRMS. [ABSTRACT FROM AUTHOR]

A one‐pot sequential strategy to construct phosphonamidates has been developed by generating phosphonites in situ from arylmagnesium bromides and triethyl phosphite followed by treatment with iodine and amines. A variety of phosphonamidates were obtained with good to excellent yields at room temperature from easily available materials. [ABSTRACT FROM AUTHOR]

Active targeting with controlled delivery of anti-inflammatory drugs to the bone is not sufficiently explored. In this study, concise and novel synthesis of a hydroxy-bisphosphonic acid (HBPA) prodrug containing ibuprofen is described. The key step consisted of preparing the HBPA function from a carboxylic acid precursor, in mild conditions and using appropriate Arbuzov reactions with tris(trimethylsilyl)phosphite. This prodrug would be an excellent candidate for the treatment of bone inflammation diseases such as rheumatoid arthritis. [ABSTRACT FROM AUTHOR]

An efficient synthesis of a series of γ-ketoallylphosphonates through a direct conversion of both primary and secondary Morita–Baylis–Hillman (MBH) alcohols by trialkyl phosphites with or without DMAP, used as additive, and under solvent-free conditions, is described herein for the first time. Subsequently, a highly regioselective Luche reduction of the primary phosphonate 2a (R = H) gave the corresponding γ-hydroxyallylphosphonate 5 that further reacted with tosylamines in the presence of diiodine (15 mol %) as a catalyst, affording the corresponding SN2-type products 6a–d in 63 to 70% isolated yields. Alternatively, the alcohol 5 produced the corresponding acetate 7 which, mediated by Ce(III), was successfully converted into the corresponding γ-aminoallylphosphonates 8a–d.

A visible light‐induced formation of Aryl‐Phosphorous bonds starting from arylazo sulfones and triaryl (or trialkyl)phosphites in the absence of any photoredox catalyst and any additives was developed. This reaction showed a broad substrate scope and afforded (hetero)aryl phosphonates in good yields and in up to the gram scale. [ABSTRACT FROM AUTHOR]

Pyrrolidine-based phosphonates, analogues of the natural amino acid proline, possess a diverse set of biological activity. The goal of this short review is to summarize the major developments in the synthesis of phosphaproline derivatives reported since 2004 with special emphasis on the mechanisms and limitations of the methods presented. 1 Introduction 2 Phosphorylation of Pyrrolidine Derivatives 2.1 Syntheses via Pudovik Reaction 2.2 Syntheses via Arbuzov Reaction 2.3 Decarboxylative Phosphorylation of Proline 2.4 Direct C–H Bond Phosphorylation 2.5 Other Reactions 2.6 Overview of Phosphorylation Methods 3 Synthesis of 2-Phosphorylpyrrolidines from Acyclic Precursors 3.1 Cyclization of 4-Substituted Butylamine Derivatives 3.2 [3+2]-Dipolar Cycloaddition of α-Iminophosphonates 3.3 Cyclization of Aminoalkynes and 4-Aminocarbonyl Compounds 4 Conclusions [ABSTRACT FROM AUTHOR]

The synthesis of two bifunctional compounds bearing a terminal hydroxy-bisphosphonic function (HBP) was achieved following a linear and a convergent strategy. In the linear approach, the free hydroxy-bisphosphonic function was introduced in the last step of the synthesis, under neutral conditions using an Arbuzov reaction with tris(trimethylsilyl) phosphite and a carboxylic acid precursor activated in situ with catecholborane. In the convergent approach, Huisgen type cycloaddition was studied starting from an HBP-functionalized alkyne partner to obtain the targeted bifunctional molecule. These complementary approaches allow for the preparation of complex bone-targeting molecules as potential prodrug candidates. [ABSTRACT FROM AUTHOR]

Reactions of 2-and 3-furoyl chlorides having chloromethyl or butylthiomethyl group in the adjacent position of the furan ring as well as of analogous N-morpholinomethylfuroyl chloride hydrochlorides with triethyl phosphite have been studied. The synthesized chloromethylfuroyl phosphonates have given the corresponding products of nucleophilic substitution in the reactions with sodium azide and potassium thiocyanate in the case of 4-chloromethyl-3-furoyl phosphonate. In the reaction of 3-chloromethyl-2-furoyl phosphonate with sodium azide, cleavage of the P-C bond takes place simultaneously with nucleophilic substitution. Potassium thiocyanate forms 3-thiocyanatomethyl-2-furoyl phosphonate in the reaction with this substance. The synthesized stable furoyl phosphonates enter the Wittig reaction with resonance-stabilized phosphoranes to give phosphorylated furylalkenes. If these compounds carry a chloromethyl group in the furan ring, they react with sodium azide and potassium thiocyanate to give the corresponding products of nucleophilic substitution. Analogously, aminomethyl derivatives have been obtained in the reaction with morpholine at room temperature. [ABSTRACT FROM AUTHOR]

The possible combinations and connections of microwave (MW) and catalysts are discussed. MW-assisted reactions, such as the direct esterification or the alkylating esterification of phosphinic acids may be enhanced by an ionic liquid additive or a phase transfer catalyst (PTC), respectively. It is also possible that a catalytic transformation, like the Arbuzov reaction with aryl halides is promoted by MW irradiation. Moreover, it is also an option exemplified by the Kabachnik–Fields reaction, by the deoxygenation of phosphine oxides, or by the PTC alkylation of P = O functionalized active methylene containing substrates that MW irradiation substitutes the catalysts. Last but not least, as it is in the Hirao reaction, MWs may make possible the simplification of the catalyst system possible. [ABSTRACT FROM AUTHOR]

5-Chloromethyl-2-furoyl chloride when treated with triethyl phosphite has given 5-chloromethyl-2-furoyl phosphonate. This compound has reacted with sodium azide in the presence of potassium iodide to give 5-azidomethyl-2-furoyl phosphonate. Treatment of 5-chloromethyl-2-furoyl phosphonate with secondary amines even under mild conditions has caused cleavage of P–C bond with liberation of diethyl hydrogen phosphite and formation of 5-chloromethyl-2-furancarboxamide. Butanthiol in the presence of potassium carbonate in acetonitrile has converted the chloromethyl group into the butylthiomethyl one and simultaneously split the P–C bond with the formation of the corresponding thioester. Under the action of S-methylthiuronium iodide and triethylamine, 5-chloromethyl-2-furoyl phosphonate has been unexpectedly reduced into the 5-methyl derivative. 5-Butylthiomethyl- and 4-(N-morpholinomethyl)-2-furoul chlorides have been phosphorylated with triethyl phosphite into the corresponding 5-functionalized 2-furoyl phosphonates. The prepared furoyl phosphonates have reacted with resonance-stabilized phosphoranes to give phosphorylated derivatives of 3-(furyl)acrylates and 4-(furyl)but-3-en-2-one with trans-location of phosphoryl and carbonyl groups with respect to the double bond. [ABSTRACT FROM AUTHOR]

The usual advantage of microwave (MW) assistance is making organic reactions faster and more efficient. In this article we present reaction types from organophosphorus chemistry, when MW-assisted transformations (e.g. the direct esterification and alkylating esterification of phosphinic acids) may be promoted by suitable catalysts, or vice versa, when a catalytic reaction is enhanced by MW irradiation (e.g. the Arbuzov reaction of aryl halides), and when catalysts may be omitted or simplified under MW irradiation as shown by the alkylation of active methylene containing P=O substrates/the Kabachnik–Fields reaction/deoxygenation of phosphine oxides, and the Hirao reaction, respectively. [ABSTRACT FROM AUTHOR]

Addition of diethyl- and diisopropyl hydrogen phosphites to isomeric (methoxycarbonyl)-2- and 3-furaldehydes in the presence of sodium ethylate or potassium fluoride led to the formation of the corresponding hydroxyphosphonates. When treated with DMSO-acetic anhydride mixture at room temperature these compounds were selectively oxidized to the corresponding furoyl phosphonates. 2-Methoxycarbonyl-3- furoyl phosphonate was synthesized via the Arbuzov reaction from 2-methoxycarbonyl-3-furoyl chloride and triethyl phosphite. The obtained isomeric (methoxycarbonyl)furoylphosphonates regardless of the structure of heterocyclic fragment react with ethoxycarbonylmethylenetriphenylphosphorane to give ethyl 3-(furyl)-3-(dialkoxyphosphoryl) acrylates with trans-location of phosphoryl and carbonyl groups against the double bond. [ABSTRACT FROM AUTHOR]

New synthetic approach to (E)-2-aryl/hetarylvinyl- 4-phenyl-quinoline-3-carboxylic acids was developed, featuring three different synthetic transformations, namely the Arbuzov reaction, in situ Horner-Emmons olefination and subsequent ester hydrolysis occurring as a one-pot procedure. The molecular structures of newly synthesized products were confirmed by spectral data and elemental analysis. [ABSTRACT FROM AUTHOR]

An efficient synthesis of a new series of organophosphorus compounds having a cyclic sulfamidates moiety is described. The cyclic sulfamidate precursors were prepared from α-amino acids after four steps (Reduction,N-Boc protection, cyclization and cleavage). The novel organophosphonates were synthesized within two steps starting from the cyclic sulfamidate (chloroacetylation following by phosphorylationviaArbuzov reaction). A particular compound7-a(diethyl phosphonate {2-[(4S)-4-benzyl-1,2,3-oxathiazolidin-3-yl-2,2-dioxyde]-2-oxoethyl}) was essayed for theirin vitrocytotoxic activities against a panel of four cell lines (Jurkat, K562, U266, and A431). For all of these cells, the synthesized compound showed low cytotoxicity, even at high concentration levels (4 mM). [ABSTRACT FROM PUBLISHER]

In the title salt solvate, C24H32O2P+·Br−·CHCl3, the P atom has a distorted tetrahedral geometry, and the planes of the phenyl rings form a dihedral angle of 71.86 (14)° with one another. The bromide anion is disordered and was modelled over three positions (occupancy ratio 0.50:0.35:0.15). The crystal also contains one disordered chloroform solvent molecule that was modeled over three positions (occupancy ratio 0.50:0.35:0.15). Weak intermolecular interactions (C—H...Br and C—H...O) exist between the complex cation and the bromide anion fragments. The resulting supramolecular structure is an oval-shaped arrangement of phosphonium salt molecules that surround the disordered bromide anion.

Reaction of ethyl 2-bromomethyl-5-(1,2,3-thiadiazol-4-yl)furan-3-carboxylate with nucleophiles of different nature was studied. It is shown that substitution of bromine with acetoxy group takes place under the action of sodium acetate in the acetic acid. Stronger bases, like phenolates, cause considerable decomposition of the labile furylthiadiazole fragment Decomposition can be avoided only when this reaction is carried out in the presence of a phase transfer catalyst under the conditions of the ion pair extraction,. In the reaction with sodium N, N-diethyl dithiocarbaminate the corresponding thioester is formed. Butanethiol and thiophenol are alkylated as potassium thiolates. In the last case S-alkylation proceeds exclusively. Reaction with excess 2-aminoethanol permits to prepare secondary amine, and the reactions with pyrrolidine, piperidine, and morpholine give the corresponding tertiary amines. Phosphorylation with triethyl phosphite under the conditions of Arbuzov reaction leads to the corresponding diethyl phosphonate. In all these transformations furylthiadiazole fragment is retained. [ABSTRACT FROM AUTHOR]

By the interaction of 2-bromomethyl-5-trifluoromethyfuran with triethyl phosphite under the Arbuzov reaction conditions diethyl (5-trifluoromethylfur-2-yl)methanephosphonate was prepared. Due to deactivation of the furan ring this substance does not enter chloromethylation even at 70°C. Because of CH-acidity of the diethoxyphosphorylmethyl fragment diethyl (5-trifluoromethylfur-2-yl)methanephosphonate in the presence of sodium foil enters the Claisen reaction with ethyl formate and diethyl oxalate. Respective derivatives of furylacetaldehyde and furylpyruvic acid and their sodium salts were isolated and characterized. Reactions of the compounds obtained with methyl iodide and diethyl chlorophosphate were studied. It was shown that trifluoromethyl derivative of phosphorylated furylacetaldehyde forms stable enol ethers and esters. The furylpyruvic acid derivative is alkylated with methyl iodide at the carbon atom adjacent to phosphorus and the compound formed undergoes cleavage to 1-(5-trifluoromethylfur-2-yl)ethanephosphonate. [ABSTRACT FROM AUTHOR]

The present study describes a convenient method for the synthesis of new N-acylsulfonamides containing phosphonate moiety. The N-acylsulfonamides were prepared starting from chlorosulfonyl isocyanate (CSI) in four steps (carbamoylation, sulfamoylation, deprotection, and acylation). Trimethylphosphite has been used to introduce the phosphonate moiety into N-acylsulfonamides via Arbuzov reaction. [ABSTRACT FROM AUTHOR]

Different aliphatic and aromatic acyl phosphonates were synthesized using Arbuzov reaction and subjected to Oxo-Diels-Alder (ODA) reaction with 2,3-dimethyl-1,3-butadiene at −78°C. AlCl3was found the best catalyst to obtain the desired ODA products from acyl phosphonates in only 30 min at low temperature, as compared to 100°C—previously reported. The same reaction was repeated at room temperature but, instead of ODA, Wittig-type product was obtained. All the products were characterized by NMR spectroscopy and mass spectrometry.1H,31P and13C,31P couplings were observed in the NMR spectra. [ABSTRACT FROM AUTHOR]

The present study a series of (E)-5-methoxy-2-styryl-4 H-pyran-4-ones 6a, 6b, 6c, 6d, 6e, 6f, 6g, 6h, 6i, 6j was synthesized and evaluated for growth inhibitory inhibition against carcinoma cells. The growth inhibition study of eight carcinoma cell lines was examined and demonstrated that SKHep cells exhibit significant in response to the tested compounds. Among them, 6f showed the most potent activity against SKHep, A549, AGS, and H460 cell lines with GI50 values of 0.17, 8.3, 3.6, 8.0 μM, respectively. [ABSTRACT FROM AUTHOR]

The synthesis of two new series of functionalized phosphonates is described. A new entry for the synthesis of 5-phosphonoalkyl cyclosulfamides and bis(phosphonoalkyl) sulfamides starting from dihalogeno bis(amino) sulfone has been developed. These compounds have been synthesized in good yields. Triethylphosphite has been used to introduce the phosphonate moiety into sulfamides and cyclosulfamides via Arbuzov reaction. [ABSTRACT FROM AUTHOR]

Baylis–Hillman adducts 3-hydroxyl-2-methylene alkanoates have been converted in one pot into the corresponding (Z)-allyl phosphonates by treatment with FeCl3 and trialkyl phosphites in toluene under reflux. The products are formed in excellent yields (88–98%) within 1–1.5 h. The process is highly convenient and efficient, cost-effective, and remarkably stereoselective. [ABSTRACT FROM AUTHOR]

A new series of modified α-amidophosphonates (or β-ketophosphonate) was synthesized by an efficient method, starting from aminoesters and chloroacetyl chloride. We have established that chloroacetyl chloride is a suitable reagent allowing the introduction a halogen moiety for the Arbuzov reaction. The α-amidophosphonates were prepared in two steps (acetylation, phosphorylation). Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

A new and efficient method for the synthesis of alkyl and aryl phosphorothioates in high yields via the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorin-2-yl)disulfanyl derivatives with trimethyl phosphite is described. [ABSTRACT FROM AUTHOR]

Abstract: An efficient method was developed for the nickel-catalyzed phosphonylation of aryl triflates with triethyl phosphite, in which KBr as an additive promoted the SN2 catalytic step. To the best of our knowledge, this is the first example of nickel-catalyzed Arbuzov reactions of aryl triflates. Most of the substrates showed good reactivity under this catalytic system. [Copyright &y& Elsevier]

The facile synthetic approaches to a wide range of potentially biologically active compounds bearing the cyclic 1,3,2-oxazaphosphinane moiety as a 'cell transport' and the residues of formic, acetic, and amino acids or 3,5-bis(benzylidene)piperidone framework have been developed. The methods are based on the Arbuzov reaction of preformed cyclic P(III) esters with chloroacetic or chloroformic acid esters, where the nature of the reactants influences the ratio of cyclic and linear products, cyclizations of susbstituted dichlorophosphoryl compounds with aminopropanols, or amination of P-isothiocyanates. [ABSTRACT FROM AUTHOR]

Abstract: A number of polyhalogenoalkyl-containing phosphonates with an enaminone core were synthesized from readily available β-alkoxyvinyl polyhalogenoalkyl ketones by successive bromination, amination, and Arbuzov reaction. The new phosphonates were used for the syntheses of five- and six-membered heterocycles bearing both trifluoromethyl and methylenephosphonate groups. [ABSTRACT FROM AUTHOR]

The article presents a study which showed the Arbuzov reactions of alkyl halides with phosphorus(III)resorcinarenes. Methods in obtaining the target compounds and reactions of octaphosphinanylresorcinarenes with methyl iodide are offered. Results showing the optimal conditions for reactions of octaphosphinanylresorcinarenes which provided formation of new derivatives bearing reactive haloalkyl fragments.

The synthesis and antiviral evaluation of new 3'-O-phosphonoethyl modified phosphonate nucleosides related to PMDTA and PMDTT is described. The reaction scheme starts from protected L-threose and the phosphonate group is introduced by the Arbuzov reaction. The 2'-OH as well as the 2'-deoxygenated nucleosides have been obtained. Unfortunately, none of these synthesized compounds shows activity against HIV and HCV. [ABSTRACT FROM AUTHOR]

Three solanesyl phosphonates were synthesized using standard Arbuzov reaction, and their structures were determined by ESI-MS, NMR, and IR. [ABSTRACT FROM AUTHOR]

Abstract: A convenient method has been developed to synthesize diaryl arylphosphonates from triaryl phosphites, triethyl phosphite, and aromatic halides. The new method relies on the triethyl phosphite assisted nickel catalyzed Arbuzov reaction and can be applied to synthesize certain diaryl alkylphosphonates without catalysts. [Copyright &y& Elsevier]

Arbuzov reaction of phenyl phosphorodichloridite with two equiv of alcohol, or mixture of one equiv of alcohol and one equiv of tert -butyl alcohol, led to the corresponding aryl H-phosphonate diesters. Following displacement of the H-phosphonate diesters with unprotected nucleosides chemoselectively produced nucleoside 5′-H-phosphonate diesters in good yields, respectively. [ABSTRACT FROM AUTHOR]

Arbuzov reactions of the fluorous primary iodides Rfn(CH2)mI [Rfn = CF3(CF2)n-1; n/m = 6/2, 8/2, 8/3, 10/2] and P(OEt)3 (excess, 160 °C) give the fluorous phosphonates Rfn(CH2)mP(O)(OEt)2 (56-59%), which are reduced with LiAlH4 to the title compounds Rfn(CH2)mPH2 (62-78%). Fluorophilicities (CF3C6F11/toluene partition coefficients) increase with the length of the Rfn moiety, decrease with the length of the (CH2)m moiety, and decrease in the functional group sequence Rfn(CH2)mNH2 > Rfn(CH2)mPH2 > Rfn(CH2)mP(O)(OEt)2. [ABSTRACT FROM AUTHOR]

A simple, efficient and general method has been developed for synthesis of 4-(phosphonomethyl)benzene derivatives through one-pot reaction of phosphoric acid, 4-substitute benzyl chlorides and hexamethyldisilazane under solvent-free conditions and the following hydrolysis in 2M NH4OH. [ABSTRACT FROM AUTHOR]

The synthesis and structure of new tetrahydroxythiacalix[4]arenes, existing in the cone conformation and possessing reactive bromide, chloromethyl or diorganylphosphoryl groups on the upper rim of the macrocycle are described. The molecular structure of tetrakis(diisopropoxyphosphorylmethyl)thiacalix[4]arene was examined by X-ray crystallography. [Copyright &y& Elsevier]

The synthesis of three novel phosphonobile acids from natural bile acids is reported. The CMC of phosphonodeoxycholic acid (PDCA) at pH 8.2 was found to be lower than that of the parent deoxycholic acid (DCA). PDCA micelles were also found to have higher microviscosity compared to DCA micelles, suggesting higher hydrophobicity and tighter packing in the interior of PDCA micelles. PDCA aggregated further to form an aqueous gel at pH 4. [Copyright &y& Elsevier]

An approach for the synthesis of moenomycin A12 C-glycoside partial structures is reported. [Copyright &y& Elsevier]

Phosphate functionalized graphene oxide (PGO) was successfully prepared by Arbuzov reaction and employed for adsorption of resorcinol from an aqueous phase. The phosphate functional groups were successfully incorporated onto the PGO surface by the formation of P–C bonds as identified by the analysis of FTIR and XPS spectra. The evaluation of adsorption capacity of resorcinol onto PGO exhibited significant improvement of resorcinol removal, achieving an adsorption capacity of 50.25 mg/g in the pH range of 4–7 which was 15 times higher than pristine graphene oxide. The addition of 2.4 M and 5 M NaCl in the adsorption system significantly increased the adsorption capacity towards resorcinol from 50.25 mg/g to 82.10 mg/g and 128.10 mg/g, respectively. Based on kinetics and adsorption isotherm studies, Pseudo-First-Order and Langmuir model are the best model to describe the adsorption process indicating that the adsorption is dominantly controlled by physisorption. The thermodynamic analysis suggested that the adsorption process was the favorable, spontaneous, and endothermic process. Besides, the interplay of hydrogen bonding and π-π interactions is proposed to be the governing physisorption mechanism. The outstanding reusability and better adsorption performance make PGO a promising adsorbent for environmental remediation of resorcinol. [Display omitted] • Phosphate functionalized graphene oxide (PGO) is synthesized via Arbuzov Reaction. • PGO performs 15 times higher than GO in the adsorption capacity of resorcinol. • PGO behaves an excellent reusability for the resorcinol adsorption. • The physical adsorption is identified to be the primary adsorption mechanism. • The interplay of hydrogen bonding and π-π interactions enhances adsorption behavior. [ABSTRACT FROM AUTHOR]

A letter to the editor in response to the article "Formation of phosphorus-carbon bond in the course of amidoalkylation of hydrophosphorylic compounds," that was published in a previous issue of the journal is presented.