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Journal articles on the topic 'Phosphonate(benzofuryl-2 o,o-dialkyl)'

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Published: 4 June 2021

Last updated: 13 February 2022

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1

Mitova, V., N. Koseva, and K. Troev. "Study on the Atherton–Todd reaction mechanism." RSC Adv. 4, no. 110 (2014): 64733–36. http://dx.doi.org/10.1039/c4ra10228b.

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A new mechanism of the Atherton–Todd reaction is discussed. The first step of the reaction between diesters of H-phosphonic acid and carbon tetrachloride in the presence of a base is a salt formation between carbon tetrachloride and the base [amine·Cl]<sup>+</sup>CCl<sub>3</sub><sup>−</sup>. The trichloromethanide anion [CCl<sub>3</sub><sup>−</sup>] deprotonates dialkyl H-phosphonate to form chloroform and dialkyl phosphonate anion [(RO)<sub>2</sub>P(O)]<sup>−</sup>. The latter anion reacts with the chlorine cation to furnish dialkyl chlorophosphate.

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2

Rádai, Zita, Nóra Zsuzsa Kiss, Mátyás Czugler, Konstantin Karaghiosoff та György Keglevich. "The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates". Acta Crystallographica Section C Structural Chemistry 75, № 3 (2019): 283–93. http://dx.doi.org/10.1107/s2053229619001839.

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The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C9H13O4P, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, C11H17O6P, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, C10H15O4P, dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate, C10H14NO6P, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, C21H20NO6P, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, C21H20ClO4P, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate,

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3

Shankar, Ravi, Meenal Asija, Nisha Singla, Gabriele Kociok-Köhn, and Kieran C. Molloy. "Synthesis, characterization and hydrolytic stability of diorganotin(IV)bis(O-alkyl alkylphosphonate)s." Canadian Journal of Chemistry 92, no. 6 (2014): 549–55. http://dx.doi.org/10.1139/cjc-2013-0486.

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Diorganotinbis(O-alkyl alkylphosphonate)s, R2Sn(O2P(OR1)R1)2 [R1 = Me, R = Me (1), Et (2), n-Bu (3); R1 = Et, R = Me (4), Et (5), n-Bu (6)] have been synthesized from the reaction between dimethyl/diethyl/di-n-butyltin dichloride and dialkyl alkylphosphonates, (R1O)2P(O)R1, in a solvent-free medium (120 °C, 18 h). X-ray crystal structure of 1 reveals two independent molecules in the unit cell that form one-dimensional polymeric motifs by virtue of bridging bidentate phosphonate groups. The structural attribute of each polymeric chain represents an orderly infinite array of -[Sn-O-P-O-]2 8-memb

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4

Voronkov, M. G., V. A. Pestunovich, N. F. Chernov, et al. "Intramolecular O → Si donor-acceptor interaction in R2P(=O)CH2CH2SiF3 molecules: Synthesis of dialkyl [2-(trifluorosilyl)ethyl]phosphonate and bis[(chloromethyl)dimethylsilyl] styrylphosphonate." Russian Journal of General Chemistry 76, no. 10 (2006): 1554–61. http://dx.doi.org/10.1134/s1070363206100082.

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5

Głowacka, Iwona E., Anna Hartwich, Iwona Rozpara, and Dorota G. Piotrowska. "Synthesis of Functionalized Diethyl (pyrrolidin-2-yl)Phosphonate and Diethyl (5-oxopyrrolidin-2-yl)Phosphonate." Molecules 26, no. 11 (2021): 3160. http://dx.doi.org/10.3390/molecules26113160.

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Short and efficient syntheses of functionalized (pyrrolidin-2-yl)phosphonate and (5-oxopyrrolidin-2-yl)phosphonate have been developed. The synthetic strategy involved the diastereospecific 1,3-dipolar cycloaddition of N-benzyl-C-(diethoxyphosphoryl)nitrone to cis-1,4-dihydroxybut-2-ene and dimethyl maleate, respectively. O,O-Diethyl 3-carbamoyl-4-hydroxy(5-oxopyrrolidin-2-yl)phosphonate was obtained from O,O-diethyl 2-benzyl-4,5-dimethoxycarbonyl(isoxazolidin-3-yl)phosphonate by hydrogenation and subsequent treatment with ammonia, whereas transformation of O,O-diethyl 2-benzyl-4,5-dihydroxyme

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6

Selas, Asier, María Fuertes, Estela Melcón-Fernández, et al. "Hybrid Quinolinyl Phosphonates as Heterocyclic Carboxylate Isosteres: Synthesis and Biological Evaluation against Topoisomerase 1B (TOP1B)." Pharmaceuticals 14, no. 8 (2021): 784. http://dx.doi.org/10.3390/ph14080784.

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This work describes, for the first time, the synthesis of dialkyl (2-arylquinolin-8-yl)phosphonate derivatives. The preparation was carried out through a direct and simple process as a multicomponent Povarov reaction of aminophenylphosphonates, aldehydes, and styrenes and subsequent oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or, alternatively, by a cycloaddition reaction between phosphonate aldimines and acetylenes. Based on phosphonate group structural characteristics, considered as phosphorous isosteres of carboxylic heterocycles, they may present interesting biological p

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7

Alexander, Petr, Antonín Holý, and Milena Masojídková. "Preparation of 9-(2-Phosphonomethoxyethyl)adenine Esters as Potential Prodrugs." Collection of Czechoslovak Chemical Communications 59, no. 8 (1994): 1853–69. http://dx.doi.org/10.1135/cccc19941853.

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Esters of 9-(2-phosphonomethoxyethyl)adenine with substituted aliphatic alcohols were prepared as potential prodrugs. Activation of the phosphonate moiety with dimethylchloromethyleneammonium chloride, generated by reaction of thionyl chloride or triphosgene with dimethylformamide, proved to be the method of choice. The esters were also prepared by alkylation of the phosphonate group with dimethylformamide dialkyl acetals or a mixture of the appropriate alcohol with dimethylformamide dineopentylacetal.

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8

Rosenberg, Ivan, and Antonín Holý. "Phosphonylmethyl analogues of ribonucleoside 2',3'-cyclic phosphates and 2'(3')-nucleotide methyl esters: Synthesis and properties." Collection of Czechoslovak Chemical Communications 50, no. 7 (1985): 1507–13. http://dx.doi.org/10.1135/cccc19851507.

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2'(3')-O-Phosphonylmethylribonucleosides II, III were prepared by intramolecular cyclisation of ribonucleoside 2'(3')-chloromethanephosphonates I in alkali. Treatment of the phosphonylmethyl derivatives with dicyclohexylcarbodiimide afforded cyclic six-membered esters VI, VII which are stable in acid and easily hydrolyze in alkali. Ribonucleases A, T1, T2, U2 and spleen cPDase do not split the cyclic phosphonate ester linkage of these analogues of ribonucleoside 2',3'-cyclic phosphonates.

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9

Zajíček, Jaroslav, Ivan Rosenberg, Radek Liboska, et al. "Conformational Studies on Diribonucleoside Monophosphate Analogs Containing a Nonisosteric, Isopolar, Phosphonate-Based Internucleotide Linkage." Collection of Czechoslovak Chemical Communications 62, no. 1 (1997): 83–98. http://dx.doi.org/10.1135/cccc19970083.

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Two types of (2'-5') and (3'-5') isomers of phosphonate analogs of diribonucleotides derived from 2'-, 3'- or 5'-O-phosphonomethyl ribonucleosides, that differ in the position of methylene group in the phosphonate internucleotide linkage, have been studied in aqueous solution by NMR techniques in order to compare their basic structural features with those of the natural (3'-5') diribonucleotides. Despite the additional methylene group in the ribose-phosphate backbone, dinucleoside phosphonates are structurally and conformationally very similar to their natural counterparts.

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10

Sahu, Adarsh, Shweta Mishra, Asmita Gajbhiye, and Ram Kishore Agrawal. "Magnesium Perchlorate Catalyzed Phospha-Michael Addition of Dialkyl Phosphite to Chalcone." Current Organic Synthesis 15, no. 7 (2018): 1020–23. http://dx.doi.org/10.2174/2210315508666180103162452.

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Aim and Objective: Phosphonate possesses a broad range of applications ranging from agrochemistry to medicines. Because of the synthetic and biological importance of phosphonate, their chemistry has stimulated an increasing interest. Hence we developed an efficient and eco-friendly Mg(ClO4)2 catalyzed one pot, solvent free synthesis of phosphonate derivatives of chalcones. Materials and Methods: Magnesium perchlorate phosphonate derivatives of chalcones were synthesized. The reactions were executed at room temperature in the presence of Anhydrous Magnesium perchlorate Anhy. Mg(ClO4)2 under sol

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11

Muhammad, Mehwish Hussain, Xiao-Lan Chen, Bing Yu, Ling-Bo Qu, and Yu-Fen Zhao. "Applications of H-phosphonates for C element bond formation." Pure and Applied Chemistry 91, no. 1 (2019): 33–41. http://dx.doi.org/10.1515/pac-2018-0906.

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Abstract The readily accessible and inexpensive dialkyl H-phosphonates are important building blocks for organic synthesis. This review specifically covers our recent work on the application of H-phosphonates as reactants for C–P bond formation, and as promoters for quinoline N-oxides to synthesize 2-functionalized quinolines.

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12

Ouahrouch, Abdelaaziz, Moha Taourirte, Hassan Bihi Lazrek, Mohamed El Azhari, Joachim Engels та Jan Bats. "Synthesis and structural characterization of four related α-phosphonates". Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C1019. http://dx.doi.org/10.1107/s2053273314089803.

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α-Aminophosphonates are structural analogues of natural amino acids. They have been the subject of considerable attention due to their potential biological activities. They may be applied as enzyme inhibitors , antibacterial agents , antitumour agents or antiviral agents [4]. α -Aminophosphonates can be synthesized via the Kabachnik–Fields reaction [5] by the coupling of a carbonyl, an amine and a dialkyl phosphite unit. We report here the synthesis and crystal structures of four diethyl [(arylamino)(4-ethynylphenyl) methyl] phosphonate derivatives, namely diethyl [(4-bromoanilino) (4-ethynyl-

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13

Chen, Xin, Xu Li, Xiao-Lan Chen та ін. "A one-pot strategy to synthesize β-ketophosphonates: silver/copper catalyzed direct oxyphosphorylation of alkynes with H-phosphonates and oxygen in the air". Chemical Communications 51, № 18 (2015): 3846–49. http://dx.doi.org/10.1039/c4cc10312b.

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A highly efficient one-pot strategy has been developed for the synthesis of β-ketophosphonates directly from alkynes and dialkylH-phosphonates in the presence of widely available AgNO<sub>3</sub>/CuSO<sub>4</sub>and K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>at room temperature.

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14

Du, Zi-Yi, Yong-Rong Xie та He-Rui Wen. "Poly[aqua(μ2-4,4′-bipyridyl-κ2 N:N′)(μ2-3-phosphonatobenzenesulfonato-κ2 O:O′)copper(II)]". Acta Crystallographica Section E Structure Reports Online 63, № 11 (2007): m2766—m2767. http://dx.doi.org/10.1107/s1600536807050763.

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The title polymer, [Cu(C6H5O6PS)(C10H8N2)(H2O)] n , was synthesized by a hydrothermal method. The CuII ion is five-coordinated by one phosphonate O atom, one sulfonate O atom, two N atoms of the bipyridyl ligand and one water molecule. The coordination geometry around the metal centre can be described as slightly distorted square-pyramidal. The CuII ions are connected by bidentate bridging phosphonato-benzenesulfonate ligands, forming one-dimensional helical chains along [010], which are further bridged by bidentate 4,4′-bipyridyl ligands, generating a two-dimensional layered crystal structure

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15

Leslie, DR, та S. Pantelidis. "Intramolecular Catalysis of Dialkyl ω-Aminoalkylphosphonate Hydrolysis". Australian Journal of Chemistry 47, № 3 (1994): 545. http://dx.doi.org/10.1071/ch9940545.

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The influence that intramolecular catalysis of hydrolysis of O-alkyl S-[2-( dialkylamino )ethyl] alkylphosphonothioates by amino groups may have on the product distribution of the reaction is investigated by study of a series of model compounds. The hydrolysis of diethyl [ω-( ethylamino )alkyl] phosphonates and diethyl [ω-( diethylamino )alkyl] phosphonates has been investigated at 75°C over the pH range 8.21-11.45. Contributions to hydrolysis of the ethoxy groups by intramolecular catalysis by the amino groups have been identified for [2-(amino)ethyl]- and [3-(amino) propyl ]- phosphonates. S

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16

Ning, Lihong, Wei Wang, Yongju Liang, Hao Peng, Liwu Fu, and Hongwu He. "Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates." European Journal of Medicinal Chemistry 48 (February 2012): 379–84. http://dx.doi.org/10.1016/j.ejmech.2011.12.014.

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17

Jansa, Petr, Viktor Kolman, Alexandra Kostinová, Martin Dračínský, Helena Mertlíková-Kaiserová, and Zlatko Janeba. "Efficient synthesis and biological properties of the 2′-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates." Collection of Czechoslovak Chemical Communications 76, no. 10 (2011): 1187–98. http://dx.doi.org/10.1135/cccc2011105.

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Efficient and optimized procedure for the preparation of several acyclic nucleosides and acyclic nucleoside phosphonates substituted at the C-2′ position of the aliphatic part by the trifluoromethyl group is described. Trifluoromethyloxirane was found to be an excellent reagent for the introduction of the 1,1,1-trifluoropropan-2-ol moiety. Surprisingly, the next reaction of these 1,1,1-trifluoropropan-2-ols with the reagent for the introduction of the methylphosphonic residue afforded the desired phosphonates in very high yields and finally a novel simple and scalable procedure for the isolati

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18

Venkatramaiah, Nutalapati, Ricardo F. Mendes, Artur M. S. Silva, João P. C. Tomé, and Filipe A. Almeida Paz. "A ladder coordination polymer based on Ca2+and (4,5-dicyano-1,2-phenylene)bis(phosphonic acid): crystal structure and solution-state NMR study." Acta Crystallographica Section C Structural Chemistry 72, no. 9 (2016): 685–91. http://dx.doi.org/10.1107/s2053229616012328.

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The preparation of coordination polymers (CPs) based on either transition metal centres or rare-earth cations has grown considerably in recent decades. The different coordination chemistry of these metals allied to the use of a large variety of organic linkers has led to an amazing structural diversity. Most of these compounds are based on carboxylic acids or nitrogen-containing ligands. More recently, a wide range of molecules containing phosphonic acid groups have been reported. For the particular case of Ca2+-based CPs, some interesting functional materials have been reported. A novel one-d

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19

Roubaud, Valérie, Christel Bliek, Robert Lauricella, Francis Vila, Didier Siri, and Paul Tordo. "CONFORMATIONAL ANALYSIS OF DIALKYL (2,5-DIALKYL PYRROLIDIN-2-YL)PHOSPHONATES AND DIETHYL(2,5,5-TRIMETHYL PYRROLIDIN-2-YL)PHOSPHONATE BY X-RAY ANALYSIS, NMR AND FORCE FIELD CALCULATIONS." Phosphorus, Sulfur, and Silicon and the Related Elements 112, no. 1-4 (1996): 143–53. http://dx.doi.org/10.1080/10426509608046358.

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20

Koleva, Ana I., Nevena I. Petkova-Yankova, and Rositca D. Nikolova. "Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds." Molecules 24, no. 11 (2019): 2030. http://dx.doi.org/10.3390/molecules24112030.

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Coumarins are an important class of natural heterocyclic compounds that have attracted considerable synthetic and pharmacological interest due to their various biological activities. This review emphasizes on the synthetic methods for the preparation of dialkyl 2-oxo-2H-1-benzo- pyran-3-phosphonates and alkyl 1,2-benzoxaphosphorin-3-carboxylates. Their chemical properties as acceptors in conjugate addition reactions, [2+2] and [3+2] cycloaddition reactions are discussed.

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21

Janeba, Zlatko, Milena Masojídková, and Antonín Holý. "Alternative synthesis of 9-{3-[(diisopropoxyphosphoryl)methoxy]-2-hydroxypropyl}adenine and its free phosphonates substituted at the C-8 position of purine base." Collection of Czechoslovak Chemical Communications 75, no. 3 (2010): 371–81. http://dx.doi.org/10.1135/cccc2009569.

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For its high therapeutic effect, (S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine (HPMPA) is an important member of a class of acyclic nucleoside phosphonates (ANPs). Although its constitutional isomer, 9-[2-hydroxy-3-(phosphonomethoxy)propyl]adenine (iso-HPMPA), exhibits no antiviral activity, our general interest in C-8 substituted adenine ANPs led us to prepare certain iso-HPMPA derivatives modified at the C-8 position of adenine. Novel alkylating agent, diisopropyl {[2-(tetrahydro-2-pyranyl)oxy-3-tosyloxypropoxy]methyl}phosphonate (9), was prepared by procedure starting from allyl alcoh

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22

Arnold, Luboš, Martina Pressová, David Šaman, Martin Vogtherr, and Stefan Limmer. "Preparation of 1'-C Deuterated Synthons for RNA Synthesis by H-Phosphonate Method Aiming at Two-Dimensional NMR Secondary Structure Studies." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 389–403. http://dx.doi.org/10.1135/cccc19960389.

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1'-C Deuterated H-phosphonate synthons were prepared via a 12-step procedure starting from [1'-2H]ribose. The procedure included nucleosidation of 1'-O-acetyl-2',3',5'-O-tribenzoyl[1'-2H]ribose with appropriately protected nucleobases and preparation of nucleoside-H-phosphonates by slightly modified described procedures. The automated RNA synthesis of 5'-G*C*U*A*U*UUAU-3' and 3'-AC*G*A*U*A*AAGU-5' was performed on a Gene Assembler Plus DNA-synthesizer. These specifically deuterated oligoribonucleotides were subsequently compared with the corresponding non-deuterated sequences using 2D-NMR NOES

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23

Rajalakshmi, K., P. Santhana Gopala Krishnan, and S. K. Nayak. "Synthesis of dialkyl 2-(Methacryloyloxyethyl) phosphonates, their characterization and polymerization." Polymer Science Series B 57, no. 5 (2015): 408–16. http://dx.doi.org/10.1134/s1560090415050127.

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24

Tupychak, Mykola А., Nazariy T. Pokhodylo, and Mykola D. Obushak. "Dialkyl (2-oxopropyl)phosphonates in the synthesis of phosphorylated heterocycles." Chemistry of Heterocyclic Compounds 56, no. 9 (2020): 1125–29. http://dx.doi.org/10.1007/s10593-020-02786-2.

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25

Srivastava, Vivek. "Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction." Open Chemistry 16, no. 1 (2018): 605–13. http://dx.doi.org/10.1515/chem-2018-0065.

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AbstractWe successfully synthesized Pd@MMT clay using a cation exchange process. We characterized all the synthesized Pd@MMT clays using sophisticated analytical techniques before testing them as a heterogeneous catalyst for the Mizoroki - Heck reaction (mono and double). The highest yield of the Mizoroki-Heck reaction product was recovered using thermally stable and highly reactive Pd@ MMT-1 clay catalyst in the functionalized ionic liquid reaction medium. We successfully isolated 2-aryl-vinyl phosphonates (mono-Mizoroki-Heck reaction product) and 2,2-diaryl-vinylphosphonates (double-Mizoroki

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26

Ćurić, M., Lj Tušek-Božić та D. Vikic-Topić. "13C NMR studies of some dialkyl α-anilinobenzylphosphonates and dialkyl α-anilino-(2-hydroxybenzyl)phosphonates". Magnetic Resonance in Chemistry 33, № 1 (1995): 27–33. http://dx.doi.org/10.1002/mrc.1260330107.

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27

Li, Jing, Dapeng Dong, Yanyu Zhu, Zhengang Sun та Hui Chen. "catena-Poly[[[aquacopper(II)]-μ-2-(hydroxyphosphonato)acetato] dihydrate]". Acta Crystallographica Section E Structure Reports Online 63, № 11 (2007): m2646—m2647. http://dx.doi.org/10.1107/s1600536807047332.

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The title compound, [Cu{HO3PCH(OH)CO2}(H2O)]·2H2O, was prepared by a hydrothermal reaction. The distorted square-pyramidal coordination geometry of copper(II) is built up of one phosphonate O atom, one hydroxy O atom, two carboxylate O atoms and one water molecule. In the crystal structure, a number of O—H...O hydrogen bonds involving the hydroxy groups, carboxylate O atoms, phosphonate O atoms, and uncoordinated and coordinated water molecules are found.

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28

Asadullina, A. E., D. M. Egorov, Yu L. Piterskaya, and A. V. Dogadina. "Synthesis of dialkyl [(5-amino-1,3,4-thiadiazol-2-yl)methyl]phosphonates." Russian Journal of General Chemistry 86, no. 3 (2016): 729–30. http://dx.doi.org/10.1134/s1070363216030361.

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29

Tajti, Ádám, Nóra Tóth, Bettina Rávai, István Csontos, Pál Tamás Szabó, and Erika Bálint. "Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation." Molecules 25, no. 14 (2020): 3307. http://dx.doi.org/10.3390/molecules25143307.

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A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fi

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30

Xue, Jian-Fei, Shao-Fang Zhou, Ye-Ye Liu, Xiangqiang Pan, Jian-Ping Zou та Olayinka Taiwo Asekun. "Manganese(iii)-mediated alkenyl Csp2–P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites". Organic & Biomolecular Chemistry 13, № 17 (2015): 4896–902. http://dx.doi.org/10.1039/c5ob00404g.

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31

Pretula, Julia, Krzysztof Kaluzynski, Ryszard Szymanski, and Stanislaw Penczek. "Transesterification of oligomeric dialkyl phosphonates, leading to the high-molecular-weight poly-H-phosphonates." Journal of Polymer Science Part A: Polymer Chemistry 37, no. 9 (1999): 1365–81. http://dx.doi.org/10.1002/(sici)1099-0518(19990501)37:9<1365::aid-pola17>3.0.co;2-#.

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32

TROEV, K. "ChemInform Abstract: Dialkyl Hydrogen Phosphonates. Part 2. Substitution Reactions at Phosphorus Atom." ChemInform 25, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199448286.

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33

Ouahrouch, Abdelaaziz, Jamal Krim, Moha Taourirte, Hassan B. Lazrek, Joachim W. Engels, and Jan W. Bats. "Four related diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates." Acta Crystallographica Section C Crystal Structure Communications 69, no. 10 (2013): 1157–63. http://dx.doi.org/10.1107/s0108270113022981.

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Crystal structures are reported for four related diethyl [(arylamino)(4-ethynylphenyl)lmethyl]phosphonate derivatives, namely diethyl [(4-bromoanilino)(4-ethynylphenyl)methyl]phosphonate, C19H21BrNO3P, (I), diethyl ((4-chloro-2-methylanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C23H31ClNO3PSi, (II), diethyl ((4-fluoroanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C22H29FNO3PSi, (III), and diethyl [(4-ethynylphenyl)(naphthalen-2-ylamino)methyl]phosphonate, C23H24NO3P, (IV). The conformation of the anilinobenzyl group is very similar in all four compounds. T

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34

Holý, Antonín. "Syntheses of Enantiomeric N-(3-Hydroxy-2-phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine Bases." Collection of Czechoslovak Chemical Communications 58, no. 3 (1993): 649–74. http://dx.doi.org/10.1135/cccc19930649.

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Methods of preparation of N-(3-hydroxy-2-phosphonomethoxypropyl) (HPMP) derivatives of (2S)- and (2R)-configuration (compounds I and XXVII, respectively) are described. The general method starts from the corresponding N-(2,3-dihydroxypropyl) derivatives which were converted either into the (R)-enantiomers XIII by reaction of the base with (R)-glycidol butyrate (XII) in the presence of cesium carbonate and subsequent methanolysis, or into the (S)-enantiomers XI by alkylation of the base with (R)-2,2-dimethyl-4-tosyloxymethyl-1,3-dioxolane (V) in the presence of the same reagent. The amino group

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35

Błaziak, Damian, Piotr Guga, Agata Jagiełło, et al. "Stereoselective formation of a P–P bond in the reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates and H-thiophosphonates." Organic & Biomolecular Chemistry 8, no. 24 (2010): 5505. http://dx.doi.org/10.1039/c0ob00104j.

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36

Yang, G. S., L. Zhou, W. Du, et al. "HPLC ENANTIOMERIC SEPARATION OF o,o-DIALKYL-2-BENZYLOXYCARBONYL-AMINOARYLMETHYL-PHOSPHONATES ON CELLULOSE TRIS(3,5-DIMETHYLPHENYL CARBAMATE) AND N-(3,5-DINITROBENZOYL) LEUCINE CSPs." Journal of Liquid Chromatography & Related Technologies 24, no. 19 (2001): 3037–48. http://dx.doi.org/10.1081/jlc-100107355.

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37

Bastian, Matthias, Dong Chen, Fridrich Gregáň, Guogang Liang, and Helmut Sigel. "Ternary Complexes in Solution+ with Phosphonates as Ligands. Intramolecular Equilibria in the Mixed Ligand Cu2+ Complexes Formed by 2,2′-Bipyridyl or 1,10-Phenanthroline and the Dianion of Phosphonylmethoxyethane in Water-Dioxane Mixtures." Zeitschrift für Naturforschung B 48, no. 9 (1993): 1279–87. http://dx.doi.org/10.1515/znb-1993-0918.

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The stability constants of the mixed ligand complexes formed by Cu2+, 2,2′-bipyridyl or 1,10-phenanthroline (= Arm), and the dianion of phosphonylmethoxyethane (PME2-), ethyl phosphonate (EtP2-), methyl phosphonate (MeP2-), or D-ribose 5′-monophosphate (RibMP2-) (= R–PO32-) were determined by potentiometric pH titrations in water containing 30 or 50% (v/v) 1,4-dioxane (I = 0.1 M, NaNO3; 25°C). The corresponding results regarding water as solvent were taken from our earlier work. Previous measurements with simple phosphate monoesters, together with the present results for RibMP2-, were used to

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38

Chen, Xiao-Lan, Xu Li, Ling-Bo Qu, et al. "Peroxides as “Switches” of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates." Journal of Organic Chemistry 79, no. 17 (2014): 8407–16. http://dx.doi.org/10.1021/jo501791n.

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39

Luo, Jun, En-Jian Han, Qian Shen, et al. "Preparation of Dialkyl (2,2,2-Trifluoroethyl)phosphonates by Cu-Promoted Reactions of 1,1-Dichloro-2,2,2-trifluoroethane with HP(O)(OR)2." Organic Process Research & Development 20, no. 11 (2016): 1988–92. http://dx.doi.org/10.1021/acs.oprd.6b00312.

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40

Hamada, Yosiki, Michiharu Sugiura, Koosuke Asai, and Yoshiki Hamada. "Simple Synthetic Method of Dialkyl 1,2-Dihydro(iso)quinoline (1 or 2)-Phosphonates." HETEROCYCLES 43, no. 5 (1996): 953. http://dx.doi.org/10.3987/com-95-7319.

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41

Tang, Wu, and De-Qing Shi. "ChemInform Abstract: Synthesis and Herbicidal Activity of O,O-Dialkyl N-[2-(5,7-Dimethyl-[1,2,4]triazolo [1,5-a]pyrimidin-2-yloxy)benzoxyl]-1-amino-1-substitutedbenzyl Phosphonates." ChemInform 41, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.201024178.

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42

Li, Yan-Jun, and Hong-Wu He. "Dimethyl {1-[2-(2-fluorophenoxy)acetoxy]ethyl}phosphonate." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (2006): o1593—o1594. http://dx.doi.org/10.1107/s1600536806010737.

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43

Young, Joo Koh, та Yung Oh Dong. "A new synthesis of β-keto phosphonate from aryl epoxysulfones and dialkyl hydrogen phosphite". Tetrahedron Letters 34, № 13 (1993): 2147–48. http://dx.doi.org/10.1016/s0040-4039(00)60367-2.

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44

Vojtíšek, Pavel, Jan Rohovec, and Ivan Lukeš. "Complexes of Mercury(II) with Tetraethyl 2,2'-Bipyridyl-4,4'-diphosphonate." Collection of Czechoslovak Chemical Communications 62, no. 11 (1997): 1710–20. http://dx.doi.org/10.1135/cccc19971710.

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Complexes [Hg(bipyP2)Br2] (2), [Hg(bipyP2)BrCl] (3), and [Hg(bipyP2)Cl2] (4), where bipyP2 is tetraethyl 2,2'-bipyridyl-4,4'-diphosphonate (1), were prepared and their crystal structures were determined. Coordination of the phosphonate group was only found in 4. In this compound, the coordination sphere of Hg(II) contains two Cl atoms, two N atoms from the bipyridine chelate and O atom from phosphonate group and thus, the coordination number is five. The presence of Br atoms in the coordination sphere of complexes 2 and 3 results in the formation of tetrahedral environment (coordination number

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45

Wessolowski, Holger, Gerd-Volker Röschenthaler, Rolf Winter та Gary L. Gard. "I(E)-l,2-Difluoro-2-(pentafluoro-λ6-sulfanyl)ethenyl]phosphonates". Zeitschrift für Naturforschung B 46, № 1 (1991): 126–28. http://dx.doi.org/10.1515/znb-1991-0123.

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For the first time SF5 containing organic phosphonates, SF5CF = CFP(O)(OR1)2 have been prepared from trimethylsilylphosphites, (R1O)2POSiMe3 (R1 = Et, R1 = SiMe3) and trifluorovinylsulfur pentafluoride, SF5CF = CF2 in an Arbuzov type reaction.

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46

Janikowska, Karolina, and Sławomir Makowiec. "Simple Method for the Preparation of Dialkyl (2,3-Dihydro-1,3-thiazol-2-YL)-phosphonates." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 1 (2010): 12–20. http://dx.doi.org/10.1080/10426501003767110.

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47

Doroshenko, Iaroslav, Michael Böhme, Axel Buchholz, Lucie Simonikova, Winfried Plass, and Jiri Pinkas. "Octanuclear nickel phosphonate core forming extended and molecular structures." CrystEngComm 22, no. 41 (2020): 6900–6910. http://dx.doi.org/10.1039/d0ce01055c.

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Three new nickel(ii) phosphonate complexes {[Na<sub>2</sub>Ni<sub>8</sub>(L)<sub>6</sub>]·nSolv}<sub>m</sub> (L = SAA<sup>3−</sup> (1), BSAA<sup>3−</sup> (2), NAA<sup>3−</sup> (3); Solv = H<sub>2</sub>O, MeOH; m = ∞ (1, 2), 1 (3)) possessing a new octanuclear {Ni<sub>8</sub>} phosphonate core were obtained and studied in detail.

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48

Chen, Xiao-Lan, and et al et al. "ChemInform Abstract: Peroxides as “Switches” of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates." ChemInform 46, no. 10 (2015): no. http://dx.doi.org/10.1002/chin.201510171.

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49

Liu, Xun-Gao, Song-Song Bao, Jian Huang, et al. "Homochiral metal phosphonate nanotubes." Chemical Communications 51, no. 82 (2015): 15141–44. http://dx.doi.org/10.1039/c5cc05647k.

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A new type of homochiral metal–organic nanotubular structures based on metal phosphonates are reported, namely, (R)- or (S)-[M(pemp)(H<sub>2</sub>O)<sub>2</sub>] [M = Co<sup>II</sup> (1), Ni<sup>II</sup> (2)] [pemp<sup>2−</sup> = (R)- or (S)-(1-phenylethylamino)methylphosphonate].

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50

Lönnberg, Tuomas, Šárka Králíková, Ivan Rosenberg, and Harri Lönnberg. "Kinetics and Mechanisms for the Isomerization of Internucleosidic 3'-O-P-CH2-5' and 3'-O-P-CH(OH)-5' Linkages to Their 2',5'-Counterparts." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 859–70. http://dx.doi.org/10.1135/cccc20060859.

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Isomerization of internucleosidic 3'-O-P-CH2-5' and 3'-O-P-CH(OH)-5' phosphonate linkages to their 2',5'-counterparts has been studied over a wide pH-range. The model compounds employed are phosphonate analogs of adenylyl-(3',5')-adenosine and adenylyl-(2',5')-adenosine having either adenosine ((R,S)-1, (R,S)-2) or 5'-deoxyadenosine (3, 4) bonded to the phosphorus atom through the C5'-atom. For comparative purposes, the hydrolytic stability of C5'-hydroxyphosphonate analogs derived from 2'-deoxyadenosine ((R,S)-5) has also been studied. In addition to the expected acid-catalyzed (pH < 3) an

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