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Journal articles on the topic 'Diphenylphosphinyl radicals'

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Published: 4 June 2021
Last updated: 20 February 2023

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1

Foray, Gabriela S., Alicia B. Peñéñory, and Roberto A. Rossi. "Article." Canadian Journal of Chemistry 77, no. 5-6 (June 1, 1999): 676–80. http://dx.doi.org/10.1139/v99-037.

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The photostimulated reactions of N-cyclopropyl-N-ethyl p-toluensulfonamide (4) with diphenylphosphide ions (2) in liquid ammonia gave 1,3-bis(diphenylphosphinyl)-1-(N-ethyl)propylamine, isolated as the oxide 5, and 1,3-bis(diphenylphosphinyl)-1-propanol, isolated as the oxide 6, all of them corresponding to the aperture of the cyclopropylaminyl radical intermediate. The reaction of 4 with 2 in excess and longer reaction times gave only 5 (73% yield). The photostimulated reactions of N-(n-butyl)-N-cyclobutyl p-toluensulfonamide (13) with 2 in liquid ammonia gave, after oxidation, N-(n-butyl)-N-cyclobutyl diphenylphosphonamide (14) in 94% yield. All these reactions occur by the radical nucleophilic substitution in which aminyl radicals are intermediates. The order of the magnitude of the rate constant for the coupling reaction of a dialkylaminyl radical with 2 could be intermediate between those of the rearrangements of the cyclopropyl and cyclobutylaminyl radicals.Key words: aminyl radicals, SRN1 reactions, radical clocks, photochemistry.
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2

Busfield, WK, ID Grice, and ID Jenkins. "The Reaction of Organophosphorus Radicals With Vinyl Acetate and Acrylonitrile in the Presence of an Aminoxyl Radical Scavenger." Australian Journal of Chemistry 48, no. 3 (1995): 625. http://dx.doi.org/10.1071/ch9950625.

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The radical-trapping technique employing 1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxyl (1) as a radical scavenger has been used to study the reaction of diphenylphosphinoyl (2) and dimethoxyphosphinoyl (3) radicals with vinyl acetate and acrylonitrile. The phosphorus- centred radicals were generated by hydrogen abstraction from diphenylphosphine oxide and dimethyl phosphite respectively. Diphenylphosphine oxide was approximately three times as reactive as dimethyl phosphite towards hydrogen abstraction by t- butoxyl radicals and four times as reactive as tetrahydrofuran (towards abstraction of an α-hydrogen). Diphenylphosphinoyl radicals were found to be relatively nucleophilic and, in competition experiments, reacted about an order of magnitude faster with acrylonitrile than with vinyl acetate. Dimethoxyphosphinoyl radicals were rather less nucleophilic and reacted only twice as fast with acrylonitrile as they did with vinyl acetate. In the presence of excess aminoxyl (1), both diphenylphosphinoyl and dimethoxyphosphinoyl radicals were efficiently scavenged to produce stable phosphinic and phosphate esters respectively. The rate of scavenging was close to diffusion-controlled (c. 1.8×109 1. mol-1 s-1).
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3

Tran, Dat Phuc, Yuki Sato, Yuki Yamamoto, Shin-ichi Kawaguchi, Shintaro Kodama, Akihiro Nomoto, and Akiya Ogawa. "Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions." Beilstein Journal of Organic Chemistry 17 (April 20, 2021): 866–72. http://dx.doi.org/10.3762/bjoc.17.72.

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The homolytic cleavage of the PV(O)–PIII bond in tetraphenyldiphosphine monoxide simultaneously provides both pentavalent and trivalent phosphorus-centered radicals with different reactivities. The method using V-40 as an initiator is successfully investigated for the regio- and stereoselective phosphinylphosphination of terminal alkynes giving the corresponding trans-isomers of 1-diphenylphosphinyl-2-diphenylthiophosphinyl-1-alkenes in good yields. The protocol can be applied to a wide variety of terminal alkynes including both alkyl- and arylalkynes.
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4

Wang, Yingxia, Andreas Eichhöfer, Florian Weigend, Dieter Fenske, and Olaf Fuhr. "The coordination behavior of 2,3-bis(diphenylphosphino)maleic-N-phenylimide towards copper, silver, gold and palladium." Dalton Transactions 48, no. 20 (2019): 6863–71. http://dx.doi.org/10.1039/c8dt05003a.

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5

Zhang, Fuyi, Liming Wang, Cui Zhang, and Yufen Zhao. "Novel regio- and stereoselective phosphonyl radical addition to glycals promoted by Mn(ii)–air: syntheses of 1,2-dideoxy 2-C-diphenylphosphinylglycopyranosides." Chem. Commun. 50, no. 16 (2014): 2046–48. http://dx.doi.org/10.1039/c3cc48806c.

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The novel Mn(ii)–air promoted radical reaction of diphenylphosphine oxide with various glycals in excellent regio- and stereoselectivities generated 1,2-dideoxy-2-C-diphenylphosphinylglycopyranosides.
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6

Sueishi, Yoshimi, and Yuko Nishihara. "Spin trapping chemistry of the diphenylphosphinyl radical." Journal of Chemical Research 2001, no. 2 (February 1, 2001): 84–86. http://dx.doi.org/10.3184/030823401103169054.

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7

Alberti, Angelo, Andrew Hudson, Gian Franco Pedulli, W. Grant McGimpsey, and Jeffrey K. S. Wan. "Photochemical reactions of quinonoid compounds with phosphorus derivatives." Canadian Journal of Chemistry 63, no. 4 (April 1, 1985): 917–21. http://dx.doi.org/10.1139/v85-152.

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The photoreactions of tetraethylpyrophosphite, tetraphenylbiphosphine, diphenylphosphine oxide, and tetraethylbiphosphine disulphide with five quinones or quinonoid compounds have been studied by esr spectroscopy; [Formula: see text] and [Formula: see text] radicals add to both carbon–carbon and carbon–oxygen double bonds, whilst with [Formula: see text] and [Formula: see text] radicals only the species resulting from addition to a carbonyl group are observed. It is also reported that the photogenerated quinone triplets react with tetraethylpyrophosphite leading to the formation of diethoxyphosphonyl radicals, which in turn add to other ground state quinone molecules, the diethoxyphosphinyl adduct to a carbonyl group being also formed in the process.
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8

Parsons, Andrew, David Sharpe, and Philip Taylor. "Radical Addition Reactions of Diphenylphosphine Sulfide." Synlett 2005, no. 19 (November 4, 2005): 2981–83. http://dx.doi.org/10.1055/s-2005-921888.

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9

Wang, Yu, Wei Wang, Ruyun Tang, Zhenhua Liu, Weihua Tao, and Zhongxue Fang. "Iron(iii)-catalyzed radical α,β-aminophosphinoylation of styrenes with diphenylphosphine oxides and anilines." Organic & Biomolecular Chemistry 16, no. 42 (2018): 7782–86. http://dx.doi.org/10.1039/c8ob02151a.

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A Fe-catalyzed highly regioselective α,β-difunctionalization of vinylarenes with diphenylphosphine oxides and anilines is disclosed, in which α,β-aminophosphinoylation is efficiently and conveniently constructed with good functional compatibility and a broad substrate scope.
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10

Korth, H. G., J. Lusztyk, and K. U. Ingold. "(Diphenylphosphinoyl)oxyl: an extremely reactive oxygen-centered radical." Journal of Organic Chemistry 55, no. 2 (January 1990): 624–31. http://dx.doi.org/10.1021/jo00289a042.

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11

Ouvry, Gilles, Béatrice Quiclet-Sire, and Samir Z. Zard. "Substituted Allyl Diphenylphosphine Oxides as Radical Allylating Agents." Angewandte Chemie 118, no. 30 (July 24, 2006): 5124–28. http://dx.doi.org/10.1002/ange.200601556.

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12

Ouvry, Gilles, Béatrice Quiclet-Sire, and Samir Z. Zard. "Substituted Allyl Diphenylphosphine Oxides as Radical Allylating Agents." Angewandte Chemie International Edition 45, no. 30 (July 24, 2006): 5002–6. http://dx.doi.org/10.1002/anie.200601556.

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13

Liu, Qiang, Weibang Lu, Guanqun Xie, and Xiaoxia Wang. "Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K2S2O8." Beilstein Journal of Organic Chemistry 16 (August 12, 2020): 1974–82. http://dx.doi.org/10.3762/bjoc.16.164.

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A variety of chroman-4-ones bearing phosphine oxide motifs were conveniently synthesized from readily available diphenylphosphine oxides and alkenyl aldehydes via a metal-free tandem phosphinoylation/cyclization protocol. The reaction utilizes K2S2O8 as oxidant and proceeds in DMSO/H2O at environmentally benign conditions with a broad substrate scope and afforded the title compounds in moderate yields.
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14

Mau, Alexandre, Guillaume Noirbent, Céline Dietlin, Bernadette Graff, Didier Gigmes, Frédéric Dumur, and Jacques Lalevée. "Panchromatic Copper Complexes for Visible Light Photopolymerization." Photochem 1, no. 2 (August 4, 2021): 167–89. http://dx.doi.org/10.3390/photochem1020010.

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In this work, eleven heteroleptic copper complexes were designed and studied as photoinitiators of polymerization in three-component photoinitiating systems in combination with an iodonium salt and an amine. Notably, ten of them exhibited panchromatic behavior and could be used for long wavelengths. Ferrocene-free copper complexes were capable of efficiently initiating both the radical and cationic polymerizations and exhibited similar performances to that of the benchmark G1 system. Formation of acrylate/epoxy IPNs was also successfully performed even upon irradiation at 455 nm or at 530 nm. Interestingly, all copper complexes containing the 1,1′-bis(diphenylphosphino)ferrocene ligand were not photoluminescent, evidencing that ferrocene could efficiently quench the photoluminescence properties of copper complexes. Besides, these ferrocene-based complexes were capable of efficiently initiating free radical polymerization processes. The ferrocene moiety introduced in the different copper complexes affected neither their panchromatic behaviors nor their abilities to initiate free radical polymerizations.
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15

Lim, Sang Chul, and Yong Hae Kim. "Evidence for formation of diphenylphosphinic peroxy radical intermediate: Spin trapping and chemical reactivity of the new phosphorus radical generated from diphenylphosphinic chloride and superoxide." Heteroatom Chemistry 1, no. 3 (May 1990): 261–65. http://dx.doi.org/10.1002/hc.520010312.

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16

Rey, Patrick, Jacques Taillades, Jean Christophe Rossi, and Georges Gros. "Et3B-induced radical addition of diphenylphosphine oxide to unsaturated compounds." Tetrahedron Letters 44, no. 32 (August 2003): 6169–71. http://dx.doi.org/10.1016/s0040-4039(03)01467-9.

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17

OkJang, Doo, Dae HyanCho, and Joonggon Kim. "Diphenylphosphine Oxide: An Alternative to Organotin Hydrides in the Radical Deoxygenation of Alcohols." Synthetic Communications 28, no. 19 (October 1998): 3559–65. http://dx.doi.org/10.1080/00397919808004902.

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18

Xue, Zhigang, Seok Kyun Noh, and Won Seok Lyoo. "2-[(Diphenylphosphino)methyl]pyridine as ligand for iron-based atom transfer radical polymerization." Journal of Polymer Science Part A: Polymer Chemistry 46, no. 9 (2008): 2922–35. http://dx.doi.org/10.1002/pola.22625.

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19

Saito, Takeshi, Robert E. Medsker, H. James Harwood, and Peter L. Rinaldi. "Characterization of Chain-End Structures in Diphenylphosphinyl-Radical-Initiated Polystyrene via 3D1H/13C/31P Correlation NMR." Journal of Magnetic Resonance, Series A 120, no. 1 (May 1996): 125–28. http://dx.doi.org/10.1006/jmra.1996.0108.

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20

Fischer, Paul J., Michelle C. Neary, Aaron P. Heerboth, and Kevin P. Sullivan. "Allylnickel(II) and Allylpalladium(II) Derivatives of [(2-(Diphenylphosphino)ethyl)cyclopentadienyl]tricarbonylmetalates: Reactions with Free Radicals." Organometallics 29, no. 20 (October 25, 2010): 4562–68. http://dx.doi.org/10.1021/om1006825.

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21

Varna, Despoina, Elena Geromichalou, Georgia Karlioti, Rigini Papi, Panagiotis Dalezis, Antonios G. Hatzidimitriou, George Psomas, Theodora Choli-Papadopoulou, Dimitrios T. Trafalis, and Panagiotis A. Angaridis. "Inhibition of Cancer Cell Proliferation and Bacterial Growth by Silver(I) Complexes Bearing a CH3-Substituted Thiadiazole-Based Thioamide." Molecules 28, no. 1 (January 1, 2023): 336. http://dx.doi.org/10.3390/molecules28010336.

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Ag(I) coordination compounds have recently attracted much attention as antiproliferative and antibacterial agents against a wide range of cancer cell lines and pathogens. The bioactivity potential of these complexes depends on their structural characteristics and the nature of their ligands. Herein, we present a series of four Ag(I) coordination compounds bearing as ligands the CH3-substituted thiadiazole-based thioamide 5-methyl-1,3,4-thiadiazole-2-thiol (mtdztH) and phosphines, i.e., [AgCl(mtdztH)(PPh3)2] (1), [Ag(mtdzt)(PPh3)3] (2), [AgCl(mtdztH)(xantphos)] (3), and [AgmtdztH)(dppe)(NO3)]n (4), where xantphos = 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and dppe = 1,2-bis(diphenylphosphino)ethane, and the assessment of their in vitro antibacterial and anti-cancer efficiency. Among them, diphosphine-containing compounds 3 and 4 were found to exhibit broad-spectrum antibacterial activity characteristics against both Gram-(+) and Gram-(–) bacterial strains, showing high in vitro bioactivity with IC50 values as low as 4.6 μΜ. In vitro cytotoxicity studies against human ovarian, pancreatic, lung, and prostate cancer cell lines revealed the strong cytotoxic potential of 2 and 4, with IC50 values in the range of 3.1–24.0 μΜ, while 3 and 4 maintained the normal fibroblast cells’ viability at relatively higher levels. Assessment of these results, in combination with those obtained for analogous Ag(I) complexes bearing similar heterocyclic thioamides, suggest the pivotal role of the substituent groups of the thioamide heterocyclic ring in the antibacterial and anti-cancer efficacy of the respective Ag(I) complexes. Compounds 1–4 exhibited moderate in vitro antioxidant capacity for free radicals scavenging, as well as reasonably strong ability to interact with calf-thymus DNA, suggesting the likely implication of these properties in their bioactivity mechanisms. Complementary insights into the possible mechanism of their anti-cancer activity were provided by molecular docking calculations, exploring their ability to bind to the overexpressed fibroblast growth factor receptor 1 (FGFR1), affecting cancer cells’ functionalities.
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22

Kajiwara, Atsushi, Yoshinari Konishi, Yotaro Morishima, Wolfram Schnabel, Keiji Kuwata, and Mikiharu Kamachi. "Time-resolved electron spin resonance study on radical polymerization with (2,4,6-trimethylbenzoyl)diphenylphosphine oxide. Direct estimation of rate constants for addition reactions of diphenylphosphonyl radicals to vinyl monomers." Macromolecules 26, no. 7 (March 1993): 1656–58. http://dx.doi.org/10.1021/ma00059a025.

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23

Pavlovskaya, Marina V., and Dmitry F. Grishin. "POLYMERIZATION OF METHYL METHACRYLATE IN PRESENCE OF INITIATING SYSTEMS BASED ON IRON COMPLEXES OF VARIOUS STRUCTURES." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 3 (March 8, 2020): 30–36. http://dx.doi.org/10.6060/ivkkt.20206303.6039.

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The features of the radical polymeriation of methyl methacrylate using initiating systems based on benzoyl peroxide and iron complexes with various ligand environments, including ferrocenes containing electron-donating and electron-withdrawing substituents in cyclopentadienyl rings, as well as cyclopentadienyl carbonyl-containing derivatives of iron, have been studied. The influence of the structure of iron complexes on the kinetics of the radical polymerization of methimethacrylate, as well as the molecular weight characteristics of the synthesized polymers, was estimated. It was established that, according to the effect on the methylmethacrylate polymerization rate in the presence of the initiating systems under study, the metal complexes are arranged in the series: 1,1'-dibromoferrocene, bromo (η5-cyclopentadienyl)dicarbonyl iron>1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino- ferrocene)>ferrocene>1-di-tert-butylphosphinoferrocene>1,1-bis-di-tert-butyl-phosphino-ferrocene> bis (η5-cyclopentadienyl) dicarbonyl iron>1–bromo-1′- diphenyl phosphino ferrocene>1-diphenylphosphino-1'-di-tert-butylphosphinoferrocene. Polymers based on polymethylmethacrylate synthesized in the presence of the studied cyclopentadienyl complexes of iron and benzoyl peroxide are capable of acting as macroinitiators in postpolymerization processes. In particular, it was found that polymethylmethacrylate synthesized with the participation of 1,1′-dibromoferrocene and bromo (η5-cyclopentadienyl) dicarbonyl iron in the presence of a peroxide initiator allows the synthesis of postpolymers. Using NMR spectroscopy, it was found that methyl methacrylate-based polymers synthesized both in the presence of the above iron complexes and its analogs obtained by traditional radical polymerization have an atactic structure. Using differential scanning calorimetry, it was shown that methyl methacrylate-based polymers obtained in the presence of cyclopentadienyl and carbonyl iron complexes have a higher glass transition temperature compared to similar polymers synthesized by radical polymerization involving only the peroxide initiator. The temperature of the onset of decomposition of these polymers remains almost unchanged.
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24

Korth, H. G., J. Lusztyk, and K. U. Ingold. "(Diphenylphosphinoyl)oxyl: an extremely reactive oxygen-centered radical [Erratum to document cited in CA112(7):56112m]." Journal of Organic Chemistry 55, no. 12 (June 1990): 3966. http://dx.doi.org/10.1021/jo00299a055.

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25

Sluggett, Gregory W., Claudia Turro, Michael W. George, Igor V. Koptyug, and Nicholas J. Turro. "(2,4,6-Trimethylbenzoyl)diphenylphosphine Oxide Photochemistry. A Direct Time-Resolved Spectroscopic Study of Both Radical Fragments." Journal of the American Chemical Society 117, no. 18 (May 1995): 5148–53. http://dx.doi.org/10.1021/ja00123a018.

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26

Mitchell, Terence N., and Kerstin Heesche. "Preparation of vinylphosphines by means of free radical addition of diphenylphosphine to alkynes and allenes." Journal of Organometallic Chemistry 409, no. 1-2 (May 1991): 163–70. http://dx.doi.org/10.1016/0022-328x(91)86141-c.

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27

JANG, D. O., D. H. CHO, and J. KIM. "ChemInform Abstract: Diphenylphosphine Oxide: An Alternative to Organotin Hydrides in the Radical Deoxygenation of Alcohols." ChemInform 29, no. 49 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199849078.

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28

Zhu, San-E., Li-Li Wang, Hao Chen, Wei Yang, Anthony Yuen, Timothy Chen, Cheng Luo, et al. "Comparative Studies on Thermal, Mechanical, and Flame Retardant Properties of PBT Nanocomposites via Different Oxidation State Phosphorus-Containing Agents Modified Amino-CNTs." Nanomaterials 8, no. 2 (January 26, 2018): 70. http://dx.doi.org/10.3390/nano8020070.

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High-performance poly(1,4-butylene terephthalate) (PBT) nanocomposites have been developed via the consideration of phosphorus-containing agents and amino-carbon nanotube (A-CNT). One-pot functionalization method has been adopted to prepare functionalized CNTs via the reaction between A-CNT and different oxidation state phosphorus-containing agents, including chlorodiphenylphosphine (DPP-Cl), diphenylphosphinic chloride (DPP(O)-Cl), and diphenyl phosphoryl chloride (DPP(O3)-Cl). These functionalized CNTs, DPP(Ox)-A-CNTs (x = 0, 1, 3), were, respectively, mixed with PBT to obtain the CNT-based polymer nanocomposites through a melt blending method. Scanning electron microscope observations demonstrated that DPP(Ox)-A-CNT nanoadditives were homogeneously distributed within PBT matrix compared to A-CNT. The incorporation of DPP(Ox)-A-CNT improved the thermal stability of PBT. Moreover, PBT/DPP(O3)-A-CNT showed the highest crystallization temperature and tensile strength, due to the superior dispersion and interfacial interactions between DPP(O3)-A-CNT and PBT. PBT/DPP(O)-A-CNT exhibited the best flame retardancy resulting from the excellent carbonization effect. The radicals generated from decomposed polymer were effectively trapped by DPP(O)-A-CNT, leading to the reduction of heat release rate, smoke production rate, carbon dioxide and carbon monoxide release during cone calorimeter tests.
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29

Kulakova, Alena, Victor Khrustalev, Yan Zubavichus, Lidia Shul’pina, Elena Shubina, Mikhail Levitsky, Nikolay Ikonnikov, Alexey Bilyachenko, Yuriy Kozlov, and Georgiy Shul'pin. "Palanquin-Like Cu4Na4 Silsesquioxane Synthesis (via Oxidation of 1,1-bis(Diphenylphosphino)methane), Structure and Catalytic Activity in Alkane or Alcohol Oxidation with Peroxides." Catalysts 9, no. 2 (February 4, 2019): 154. http://dx.doi.org/10.3390/catal9020154.

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The self-assembly synthesis of copper-sodium phenylsilsesquioxane in the presence of 1,1-bis(diphenylphosphino)methane (dppm) results in an unprecedented cage-like product: [(PhSiO1,5)6]2[CuO]4[NaO0.5]4[dppmO2]2 1. The most intriguing feature of the complex 1 is the presence of two oxidized dppm species that act as additional O-ligands for sodium ions. Two cyclic phenylsiloxanolate (PhSiO1,5)6 ligands coordinate in a sandwich manner with the copper(II)-containing layer of the cage. The structure of 1 was established by X-ray diffraction analysis. Complex 1 was shown to be a very good catalyst in the oxidation of alkanes and alcohols with hydrogen peroxide or tert-butyl hydroperoxide in acetonitrile solution. Thus, cyclohexane (CyH), was transformed into cyclohexyl hydroperoxide (CyOOH), which could be easily reduced by PPh3 to afford stable cyclohexanol with a yield of 26% (turnover number (TON) = 240) based on the starting cyclohexane. 1-Phenylethanol was oxidized by tert-butyl hydroperoxide to give acetophenone in an almost quantitative yield. The selectivity parameters of the oxidation of normal and branched alkanes led to the conclusion that the peroxides H2O2 and tert-BuOOH, under the action of compound (1), decompose to generate the radicals HO• and tert-BuO• which attack the C-H bonds of the substrate.
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30

G. Reis, Samira, Miguel A. del Águila-Sánchez, Guilherme P. Guedes, Yolanda Navarro, Rafael A. Allão Cassaro, Glaucio B. Ferreiraa, Sergiu Calancea, Fernando López-Ortiz, and Maria G. F. Vaz. "Novel P,P-diphenylphosphinic amide-TEMPO radicals family: Synthesis, crystal structures, spectroscopic characterization, magnetic properties and DFT calculations." Polyhedron 144 (April 2018): 166–75. http://dx.doi.org/10.1016/j.poly.2018.01.011.

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31

Voronkov, M. G., N. M. Kudyakov, V. I. Rakhlin, A. L. Kuznetsov, M. V. Sigalov, and R. G. Mirskov. "Free-radical addition of phenyl- and diphenylphosphines to 2-vinyl-1,3-dioxa-6-aza-2-silacyclooctanes." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 11 (November 1985): 2423–24. http://dx.doi.org/10.1007/bf00956817.

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32

Duffy, Noel W., Ross R. Nelson, Michael G. Richmond, Anne L. Rieger, Philip H. Rieger, Brian H. Robinson, David R. Tyler, Jian Cheng Wang, and Kaiyuan Yang. "An EPR Study of 2,3-Bis(diphenylphosphino)maleic Anhydride (BMA) Complexes and the BMA Radical Anion." Inorganic Chemistry 37, no. 19 (September 1998): 4849–56. http://dx.doi.org/10.1021/ic980581h.

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33

Huang, Rong, Xiuyan Guo, Shiyue Ma, Jixing Xie, Jianzhong Xu, and Jing Ma. "Novel Phosphorus-Nitrogen-Containing Ionic Liquid Modified Metal-Organic Framework as an Effective Flame Retardant for Epoxy Resin." Polymers 12, no. 1 (January 5, 2020): 108. http://dx.doi.org/10.3390/polym12010108.

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Metal-organic frameworks (MOFs) have shown great potential in flame retardant applications; however, strategies for fully exploiting the advantages of MOFs in order to further enhance the flame retardant performance are still in high demand. Herein, a novel MOF composite was designed through the generated cooperative role of MOF (NH2-MIL-101(Al)) and a phosphorus-nitrogen-containing ionic liquid ([DPP-NC3bim][PMO]). The ionic liquid (IL) was composed of imidazole cation modified with diphenylphosphinic group (DPP) and phosphomolybdic acid (PMoA) anions, which can trap the degrading polymer radicals and reduce the smoke emission. The MOF acts as a porous host and can avoid the agglomeration of ionic liquid. Meanwhile, the -NH2 groups of NH2-MIL-101(Al) can increase the compatibility with epoxy resin (EP). The framework is expected to act as an efficient insulating barrier to suppress the flame spread. It was demonstrated that the MOF composite (IL@NH2-MIL-101(Al)) is able to effectively improve the fire safety of EP at low additions (3 wt. %). The LOI value of EP/IL@NH2-MIL-101(Al) increased to 29.8%. The cone calorimeter results showed a decreased heat release rate (51.2%), smoke production rate (37.8%), and CO release rate (44.8%) of EP/IL@NH2-MIL-101(Al) with respect to those of neat EP. This strategy can be extended to design other advanced materials for flame retardant.
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34

MITCHELL, T. N., and K. HEESCHE. "ChemInform Abstract: Preparation of Vinylphosphines by Means of Free Radical Addition of Diphenylphosphine to Alkynes and Allenes." ChemInform 22, no. 34 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199134201.

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35

Konarev, Dmitri V., Sergey I. Troyanov, Akihiro Otsuka, Hideki Yamochi, Gunzi Saito, and Rimma N. Lyubovskaya. "Charge transfer complexes of fullerenes containing C60˙− and C70˙− radical anions with paramagnetic CoII(dppe)2Cl+ cations (dppe: 1,2-bis(diphenylphosphino)ethane)." Dalton Transactions 45, no. 15 (2016): 6548–54. http://dx.doi.org/10.1039/c5dt04627k.

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Novel complexes {Co(dppe)2Cl}(C60) (1) and {Co(dppe)2Cl}(C70)·0.5C6H4Cl2 (2) were obtained. Charge transfer provides the formation of CoII(dppe)2Cl+ and closely packed C60˙− or C70˙− radical anions.
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36

Li, Da-Peng, Xiang-Qiang Pan, Li-Tao An, Jian-Ping Zou, and Wei Zhang. "Manganese(III)-Mediated Selective Diphenylphosphinoyl Radical Reaction of 1,4-Diaryl-1-butynes for the Synthesis of 2-Phosphinoylated 3,4-Dihydronaphathalenes." Journal of Organic Chemistry 79, no. 4 (February 4, 2014): 1850–55. http://dx.doi.org/10.1021/jo402556a.

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37

Xu, Jian, Xiaoxia Yu, and Qiuling Song. "Silver-Catalyzed Radical-Involved Cascade Cyclization of Diphenylphosphine with Cinnamamides: Access to 2-Phosphinoyl-3H-pyrrolo[1,2-a]indoles." Organic Letters 19, no. 5 (February 16, 2017): 980–83. http://dx.doi.org/10.1021/acs.orglett.6b03713.

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38

Mochizuki, Takashi, Satoshi Hayakawa, and Koichi Narasaka. "Sulfonylation and Phosphinylation of Olefinic Compounds with Radical Species Generated by the Oxidation of Sodium Sulfinates and Diphenylphosphine Oxide." Bulletin of the Chemical Society of Japan 69, no. 8 (August 1996): 2317–25. http://dx.doi.org/10.1246/bcsj.69.2317.

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39

Li, Da-Peng, Xiang-Qiang Pan, Li-Tao An, Jian-Ping Zou, and Wei Zhang. "ChemInform Abstract: Manganese(III)-Mediated Selective Diphenylphosphinoyl Radical Reaction of 1,4-Diaryl-1-butynes for the Synthesis of 2-Phosphinoylated 3,4-Dihydronaphathalenes." ChemInform 45, no. 31 (July 17, 2014): no. http://dx.doi.org/10.1002/chin.201431190.

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40

Grapperhaus, Craig A., and Selma Poturovic. "Electrochemical Investigations of the [Tris(2-(diphenylphosphino)thiaphenolato)ruthenate(II)] Monoanion Reveal Metal- and Ligand-Centered Events: Radical, Reactivity, and Rate." Inorganic Chemistry 43, no. 10 (May 2004): 3292–98. http://dx.doi.org/10.1021/ic035085u.

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41

MOCHIZUKI, T., S. HAYAKAWA, and K. NARASAKA. "ChemInform Abstract: Sulfonylation and Phosphinylation of Olefinic Compounds with Radical Species Generated by the Oxidation of Sodium Sulfinates and Diphenylphosphine Oxide." ChemInform 27, no. 51 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199651033.

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42

Anifowose, Adebanjo Jacob, Kazuhiko Takeda, and Hiroshi Sakugawa. "Novel Fluorometric Method for the Determination of Production Rate and Steady-State Concentration of Photochemically Generated Superoxide Radical in Seawater Using 3′,6′-(Diphenylphosphinyl)fluorescein." Analytical Chemistry 87, no. 24 (November 24, 2015): 11998–2005. http://dx.doi.org/10.1021/acs.analchem.5b00917.

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43

Li, Chun-Xiao, De-Shuang Tu, Rui Yao, Hong Yan, and Chang-Sheng Lu. "Visible-Light-Induced Cascade Reaction of Isocyanides and N-Arylacrylamides with Diphenylphosphine Oxide via Radical C–P and C–C Bond Formation." Organic Letters 18, no. 19 (September 28, 2016): 4928–31. http://dx.doi.org/10.1021/acs.orglett.6b02413.

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44

Konarev, Dmitri V., Alexey V. Kuzmin, Mikhail G. Andronov, Salavat S. Khasanov, Mikhail S. Batov, Akihiro Otsuka, Hideki Yamochi, Hiroshi Kitagawa, and Rimma N. Lyubovskaya. "Distortion and electronic structure of ordered C60•− radical anions in the salt with {CoI(dppe)2CO}+ cations (dppe: 1,2-bis(diphenylphosphino)ethane)." Inorganica Chimica Acta 483 (November 2018): 504–9. http://dx.doi.org/10.1016/j.ica.2018.08.046.

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45

Janssen, Rene A. J., Olav M. Aagaard, Marcoen J. T. F. Cabbolet, and Bas F. M. De Waal. "Radical cations of bis(diphenylphosphino) derivatives (Ph2P-R-PPh2): the formation of localized, cyclic, and dimeric configurations; an ESR and quantum chemical study." Journal of Physical Chemistry 95, no. 23 (November 1991): 9256–63. http://dx.doi.org/10.1021/j100176a042.

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46

JANSSEN, R. A. J., O. M. AAGAARD, M. J. T. F. CABBOLET, and B. F. M. DE WAAL. "ChemInform Abstract: Radical Cations of Bis(diphenylphosphino) Derivatives (Ph2P-R-PPh2): The Formation of Localized, Cyclic, and Dimeric Configurations. An ESR and Quantum Chemical Study." ChemInform 23, no. 8 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199208252.

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47

Mixa, Marlene M., Pamela A. Matsch, David C. Boyd, and Kent R. Mann. "Preparation, characterization, and oxidation chemistry of the dirhodium complex [Rh2(dimen)2(dppm)2](PF6)2 (dimen = 1,8-diisocyanomenthane; dppm = bis(diphenylphosphino)methane). Electrochemical generation of a stable d7-d8 radical." Inorganic Chemistry 25, no. 19 (September 1986): 3331–33. http://dx.doi.org/10.1021/ic00239a001.

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48

Parsons, Andrew F., David J. Sharpe, and Philip Taylor. "Radical Addition Reactions of Diphenylphosphine Sulfide." ChemInform 37, no. 16 (April 18, 2006). http://dx.doi.org/10.1002/chin.200616175.

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49

Takano, Hideaki, Hitomi Katsuyama, Hiroki Hayashi, Wataru Kanna, Yu Harabuchi, Satoshi Maeda, and Tsuyoshi Mita. "A theory-driven synthesis of symmetric and unsymmetric 1,2-bis(diphenylphosphino)ethane analogues via radical difunctionalization of ethylene." Nature Communications 13, no. 1 (November 21, 2022). http://dx.doi.org/10.1038/s41467-022-34546-5.

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Abstract1,2-Bis(diphenylphosphino)ethane (DPPE) and its synthetic analogues are important structural motifs in organic synthesis, particularly as diphosphine ligands with a C2-alkyl-linker chain. Since DPPE is known to bind to many metal centers in a bidentate fashion to stabilize the corresponding metal complex via the chelation effect originating from its entropic advantage over monodentate ligands, it is often used in transition-metal-catalyzed transformations. Symmetric DPPE derivatives (Ar12P−CH2−CH2−PAr12) are well-known and readily prepared, but electronically and sterically unsymmetric DPPE (Ar12P−CH2−CH2−PAr22; Ar1≠Ar2) ligands have been less explored, mostly due to the difficulties associated with their preparation. Here we report a synthetic method for both symmetric and unsymmetric DPPEs via radical difunctionalization of ethylene, a fundamental C2 unit, with two phosphine-centered radicals, which is guided by the computational analysis with the artificial force induced reaction (AFIR) method, a quantum chemical calculation-based automated reaction path search tool. The obtained unsymmetric DPPE ligands can coordinate to several transition-metal salts to form the corresponding complexes, one of which exhibits distinctly different characteristics than the corresponding symmetric DPPE–metal complex.
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50

Ouvry, Gilles, Beatrice Quiclet-Sire, and Samir Z. Zard. "Substituted Allyl Diphenylphosphine Oxides as Radical Allylating Agents." ChemInform 37, no. 48 (November 28, 2006). http://dx.doi.org/10.1002/chin.200648051.

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