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Journal articles on the topic 'Phenyl formate'

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Published: 9 March 2023

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1

Mark, Hugh, Tahira Baker, and Eric A. Noe. "Dynamic NMR studies of phenyl formate and 2,6-dimethylphenyl formate." Journal of the American Chemical Society 111, no. 17 (August 1989): 6551–53. http://dx.doi.org/10.1021/ja00199a011.

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2

Bagno, Alessandro, Willi Kantlehner, Ralf Kreß, and Giacomo Saielli. "Fries Rearrangement of Aryl Formates Promoted by BCl3. Mechanistic Evidence from 11B NMR Spectra and DFT Calculations." Zeitschrift für Naturforschung B 59, no. 4 (April 1, 2004): 386–97. http://dx.doi.org/10.1515/znb-2004-0406.

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AbstractThe Fries rearrangement of model aryl formate esters, promoted by boron trichloride, has been investigated by means of NMR spectroscopy (both experimental and computational) and by DFT calculations. Firstly, the 11B NMR chemical shifts of a series of model boron compounds have been predicted by GIAO-B3LYP/6-31G(d,p) calculations, in order to make predictions of the chemical shifts of transient reaction intermediates observable by 11B NMR. Such 11B spectra for the reaction of two esters (phenyl and 3-methyoxyphenyl formates) have been obtained, and are found to follow different patterns which can be rationalized on the basis of computed chemical shifts. Secondly, DFT calculations (B3LYP/6-31G(d,p) level) have been employed to investigate several mechanistic pathways of the rearrangement of phenyl formate. It is found that the pathways leading to the lowest activation energies are those in which formyl chloride is generated from a complex between phenyl formate and BCl3, which then acts as the formylating agent.

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3

Bredikhin, A. A., P. P. Chernov, V. V. Klochkov, and A. N. Vereshchagin. "Parameters of the conformational equilibrium in phenyl formate." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 37, no. 7 (July 1988): 1371–73. http://dx.doi.org/10.1007/bf00962742.

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4

Chang, Wenju, Jingfu Li, Wenlong Ren, and Yian Shi. "Pd-Catalyzed regioselective hydroesterification of 2-allylphenols to seven-membered lactones without external CO gas." Organic & Biomolecular Chemistry 14, no. 11 (2016): 3047–52. http://dx.doi.org/10.1039/c5ob02663f.

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5

Li, Jingfu, Wenju Chang, Wenlong Ren, Wei Liu, Haining Wang, and Yian Shi. "A palladium-catalyzed enantioselective hydroesterification of alkenylphenols with phenyl formate. A facile approach to optically active dihydrocoumarins." Organic & Biomolecular Chemistry 13, no. 41 (2015): 10341–47. http://dx.doi.org/10.1039/c5ob01431j.

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6

Yuan, Qing, Zhen-Bang Chen, Fang-Ling Zhang, and Yong-Ming Zhu. "Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source." Organic & Biomolecular Chemistry 15, no. 7 (2017): 1628–35. http://dx.doi.org/10.1039/c6ob02409b.

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7

Kopchuk, Dmitry S., Alexey P. Krinochkin, Мaria I. Valieva, Еkaterina S. Starnovskaya, Yaroslav K. Shtaitz, Svetlana S. Rybakova, Evgeny D. Ladin, Ekaterina A. Kudryashova, Elvira R. Sharafieva, and Оleg N. Chupakhin. "Improved method for the obtaining DTTA-appended 2,2’-bipyridine ligands for lanthanide cations." Chimica Techno Acta 9, no. 2 (May 30, 2022): 20229210. http://dx.doi.org/10.15826/chimtech.2022.9.2.10.

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The composition of the reaction mixture after DTTA tert-butyl ester alkylation with 6'-halomethyl-5-phenyl-2,2'-bipyridines was studied. In addition to the target product, DTTA-appended 2,2’-bipyridine, the corresponding 6'-hydroxymethyl-substituted 2,2’-bipyridine and (5'-phenyl-[2,2'-bipyridin]-6-yl)methyl formate were isolated as by-products in some cases. Finally, an improved procedure for the DTTA tert-butyl ester alkylation with 6'-halomethyl-5-phenyl-2,2'-bipyridines by using Finkelstein reaction was developed.

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8

Ren, Wenlong, Wenju Chang, Yang Wang, Jingfu Li, and Yian Shi. "Pd-Catalyzed Regiodivergent Hydroesterification of Aryl Olefins with Phenyl Formate." Organic Letters 17, no. 14 (July 2, 2015): 3544–47. http://dx.doi.org/10.1021/acs.orglett.5b01630.

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9

Wang, Shengyan, Jianing Xu, Yong Fan, Jia Jia, Lijuan Gao, Jing Sun, Liang Shan, Xiaodong Chen, Li Wang, and Hyo Jin Seo. "3D lanthanide metal–organic frameworks constructed from lanthanide formate skeletons and 3,5-bis(4′-carboxy-phenyl)-1,2,4-triazole connectors: synthesis, structure and luminescence." RSC Advances 5, no. 128 (2015): 106107–12. http://dx.doi.org/10.1039/c5ra21557a.

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10

Ning, Hongbo, Dapeng Liu, Junjun Wu, Liuhao Ma, Wei Ren, and Aamir Farooq. "A theoretical and shock tube kinetic study on hydrogen abstraction from phenyl formate." Physical Chemistry Chemical Physics 20, no. 33 (2018): 21280–85. http://dx.doi.org/10.1039/c8cp02075b.

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We performed ab initio calculations of the rate constants for H-abstraction reactions of phenyl formate (PF) by H/O/OH/HO₂ radicals and experimentally determined the rate constants for PF + OH reactions using shock tube/laser absorption methods.

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11

Yalfani, Mohammad S., Giulio Lolli, Aurel Wolf, Leslaw Mleczko, Thomas E. Müller, and Walter Leitner. "Methyl formate as a carbonylating agent for the catalytic conversion of phenol to methyl phenyl carbonate." Green Chemistry 15, no. 5 (2013): 1146. http://dx.doi.org/10.1039/c3gc36877g.

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12

Schaefer, Ted, and Glenn H. Penner. "The conformational properties of some phenyl esters. Molecular orbital and nuclear magnetic resonance studies." Canadian Journal of Chemistry 65, no. 9 (September 1, 1987): 2175–78. http://dx.doi.org/10.1139/v87-363.

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Extensive, geometry-optimized, STO-3G MO computations on phenyl formate imply a strongly nonplanar Z conformer (C=O bond cis to the phenyl group) at ambient temperatures. The internal barrier to rotation about the C(1)—O bond in this conformer is computed as V/kJ mol−1 = (−5.17 ± 0.27) sin2 θ − (2.42 ± 0.27) sin2 2θ, θ being zero for the planar conformer; the twofold is nearly twice as large as the fourfold component. The expectation value of θ is 58° at 300 K. The spin–spin coupling constants over six bonds between 13C and I9F nuclei in 4-fluorophenyl formate, acetate, propionate, and isobutyrate, as well as in the 2,6-dichloro-4-fluorophenyl acetate, are adduced as evidence for nonplanar conformers of these molecules. The magnitudes of these six-bond coupling constants are consistent with internal barriers to rotation about the C(1)—O bonds, which are similar in magnitude to those given by the computations on the Z conformer of phenyl formate. The energies of the planar and nonplanar E conformers, as well as the interconversion energies for [Formula: see text] isomerization, are computed. Small amounts of the nonplanar E conformer are predicted at ambient temperatures. The 13C chemical shifts and the one-bond 13C, 19F coupling constants are consistent, respectively, with only minor variations in the conformational behavior of the ester moieties caused by the fluorine substituent and by changes in the structures of these moieties themselves.

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13

Castanet, Yves, André Mortreux, and Francis Petit. "Palladium-catalyzed double and monocarbonylation of phenyl iodide by methyl formate." Journal of Molecular Catalysis 63, no. 3 (December 1990): 313–17. http://dx.doi.org/10.1016/0304-5102(90)85123-y.

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14

Song, Kun-Long, Bin Wu, Wan-Er Gan, Wan-Chun Yang, Xiao-Bing Chen, Jian Cao, and Li-Wen Xu. "Palladium-catalyzed gaseous CO-free carbonylative C–C bond activation of cyclobutanones." Organic Chemistry Frontiers 8, no. 13 (2021): 3398–403. http://dx.doi.org/10.1039/d1qo00467k.

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A palladium-catalyzed carbonylative C–C bond activation reaction of cyclobutanones is reported, and it affords a variety of indanones bearing ester or amide groups using phenyl formate and benzene-1,3,5-triyl triformate as CO surrogates.

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15

Bagno, Alessandro, Willi Kantlehner, and Giacomo Saielli. "Formylation of activated arenes by phenyl formate: implications for the mechanism of the Fries rearrangement of aryl formates." Journal of Physical Organic Chemistry 21, no. 7-8 (2008): 682–87. http://dx.doi.org/10.1002/poc.1356.

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16

Bhanage, Bhalchandra, Sujit Chavan, and Adithyaraj K. "In situ Generation and Utilization of CO: An Efficient Route towards N-Substituted Saccharin via Carbonylative Cyclization of 2-Iodosulfonamides." Synlett 28, no. 15 (May 18, 2017): 2000–2003. http://dx.doi.org/10.1055/s-0036-1588422.

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The present protocol demonstrates the synthesis of N-substituted saccharines via carbonylative cyclization of 2-iodosulfonamides using a Pd(OAc)2/Xantphos catalyst system and phenyl formate as a CO source. A variety of saccharin derivatives is synthesized under milder reaction conditions.

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17

Ferretti, Francesco, Manar Ahmed Fouad, and Fabio Ragaini. "Synthesis of Indoles by Palladium-Catalyzed Reductive Cyclization of β-Nitrostyrenes with Phenyl Formate as a CO Surrogate." Catalysts 12, no. 1 (January 17, 2022): 106. http://dx.doi.org/10.3390/catal12010106.

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The reductive cyclization of suitably substituted organic nitro compounds by carbon monoxide is a very appealing technique for the synthesis of heterocycles because of its atom efficiency and easiness of separation of the only stoichiometric byproduct CO2, but the need for pressurized CO has hampered its diffusion. We have recently reported on the synthesis of indoles by reductive cyclization of o-nitrostyrenes using phenyl formate as a CO surrogate, using a palladium/1,10-phenanthroline complex as catalyst. However, depending on the desired substituents on the structure, the use of β-nitrostyrenes as alternative reagents may be advantageous. We report here the results of our study on the possibility to use phenyl formate as a CO surrogate in the synthesis of indoles by reductive cyclization of β-nitrostyrenes, using PdCl2(CH3CN)2 + phenanthroline as the catalyst. It turned out that good results can be obtained when the starting nitrostyrene bears an aryl substituent in the alpha position. However, when no such substituent is present, only fair yield of indole can be obtained because the base required to decompose the formate also catalyzes an oligo-polymerization of the starting styrene. The reaction can be performed in a single glass pressure tube, a cheap and easily available piece of equipment.

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18

Schaefer, Ted, Rudy Sebastian, and Glenn H. Penner. "Long-range formyl proton coupling constants of 4-X-phenyl formats (X = H, F, CH3, NO2) and 2,6-dichlorophenyl formate. Conformations in solution." Canadian Journal of Chemistry 66, no. 8 (August 1, 1988): 1787–93. http://dx.doi.org/10.1139/v88-289.

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The signs and magnitudes of the long-range coupling constants between the formyl and ring protons over five, six, seven, and eight bonds in phenyl formate and its 4-fluoro, 4-methyl, and 4-nitro derivatives are reported. These numbers are combined with CNDO/2 and INDO MO FPT computations of their conformational dependence and with STO-3G MO populational distributions to provide a description of the conformational behaviour of these molecules. The Z conformers, predominantly nonplanar and having the carbonyl group pointing towards the ring, appear to account for more than 95% of the molecules in CS2 solution at 300 K. In polar solvents, significant populations of the E conformers are indicated by the long-range coupling constants. The long-range coupling constants for the formyl proton in 2,6-dichlorophenyl formate are consistent with geometry-optimized STO-3G MO computations, which imply that the Z conformation, with the aldehyde group lying near the plane perpendicular to the benzene plane, is again at least 95% abundant at 300 K. The proton chemical shifts are also consistent with these conclusions.

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19

Ruble, J. Craig, Christopher J. Maddocks, Sivakumar V. Aathimanikandan, and Jeffery Richardson. "Quinolin-8-yl Formate: A New Option for Small-Scale Carbonylation Reactions in Microwave Reactors." Synlett 31, no. 16 (July 17, 2020): 1608–12. http://dx.doi.org/10.1055/s-0040-1707187.

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A convenient procedure for conducting small-scale carbonylations of aryl or benzyl halides in a microwave reactor by using quinolin-8-yl formate is described. The resulting 8-acyloxyquinolines were shown to be more reactive than phenyl esters in acyl-transfer reactions, and their utility for the production of esters and amides was demonstrated.

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20

Ueda, Tsuyoshi, Hideyuki Konishi, and Kei Manabe. "Palladium-Catalyzed Carbonylation of Aryl, Alkenyl, and Allyl Halides with Phenyl Formate." Organic Letters 14, no. 12 (May 30, 2012): 3100–3103. http://dx.doi.org/10.1021/ol301192s.

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21

Ren, Wenlong, Wenju Chang, Yang Wang, Jingfu Li, and Yian Shi. "ChemInform Abstract: Pd-Catalyzed Regiodivergent Hydroesterification of Aryl Olefins with Phenyl Formate." ChemInform 46, no. 45 (October 22, 2015): no. http://dx.doi.org/10.1002/chin.201545084.

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22

Feng, Jian, Wei Xiong, Yun Jia, Jin Bo Wang, De Rong Liu, and Rui Xiang Qin. "Catalytic Transfer Hydrogenolysis of 2-Phenyl-2-Propanol with Pd/C and Formic Acid." Advanced Materials Research 287-290 (July 2011): 1749–52. http://dx.doi.org/10.4028/www.scientific.net/amr.287-290.1749.

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The catalytic transfer hydrogenolysis of 2-phenyl-2-propanol was studied over Pd/C catalyst, using formic acid and formate salts as hydrogen donors. The Pd/C catalyst was characterized by powder X-ray diffraction (XRD), inductively coupled plasma (ICP), N2 adsorption/desorption and transmission electron microscopy (TEM). The effects of hydrogen donor, molar ratio of formic acid to 2-phenyl-2-propanol and water content were evaluated. Under mild reaction conditions (80 °C, 2h), 2-phenyl-2-propanol can be hydrogenolyzed to isopropylbenzene with very high selectivity (96.5%) and high conversion (92.8%) in the presence of Pd/C and formic acid. From the viewpoint of environmental friendly principles, this study may open the way to a new approach for the production of propylene oxide.

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23

Yalfani, Mohammed S., Giulio Lolli, Aurel Wolf, Leslaw Mleczko, Thomas E. Mueller, and Walter Leitner. "ChemInform Abstract: Methyl Formate as a Carbonylating Agent for the Catalytic Conversion of Phenol to Methyl Phenyl Carbonate." ChemInform 44, no. 34 (August 1, 2013): no. http://dx.doi.org/10.1002/chin.201334070.

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24

Li, Jingfu, Wenju Chang, Wenlong Ren, Jie Dai, and Yian Shi. "Palladium-Catalyzed Highly Regio- and Enantioselective Hydroesterification of Aryl Olefins with Phenyl Formate." Organic Letters 18, no. 21 (October 25, 2016): 5456–59. http://dx.doi.org/10.1021/acs.orglett.6b02467.

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25

Yalfani, Mohammad S., Giulio Lolli, Thomas E. Müller, Aurel Wolf, and Leslaw Mleczko. "MethylN-Phenyl Carbamate Synthesis from Aniline and Methyl Formate: Carbon Recycling to Chemical Products." ChemSusChem 8, no. 3 (December 12, 2014): 443–47. http://dx.doi.org/10.1002/cssc.201402827.

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26

Ueda, Tsuyoshi, Hideyuki Konishi, and Kei Manabe. "ChemInform Abstract: Palladium-Catalyzed Carbonylation of Aryl, Alkenyl, and Allyl Halides with Phenyl Formate." ChemInform 43, no. 41 (September 13, 2012): no. http://dx.doi.org/10.1002/chin.201241080.

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27

Toda, Hideaki, Yuta Uetake, Yumi Yakiyama, Hironobu Nakazawa, Takashi Kajitani, Takanori Fukushima, and Hidehiro Sakurai. "Sumanene Hexaester: An Electron-Deficient Buckybowl." Synthesis 51, no. 24 (September 30, 2019): 4576–81. http://dx.doi.org/10.1055/s-0039-1690206.

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2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO2Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.

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28

Konishi, Hideyuki, Hiroki Nagase, and Kei Manabe. "Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source." Chemical Communications 51, no. 10 (2015): 1854–57. http://dx.doi.org/10.1039/c4cc09413a.

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29

Wang, Haining, Ben Dong, Yang Wang, Jingfu Li, and Yian Shi. "A Palladium-Catalyzed Regioselective Hydroesterification of Alkenylphenols to Lactones with Phenyl Formate as CO Source." Organic Letters 16, no. 1 (December 12, 2013): 186–89. http://dx.doi.org/10.1021/ol403171p.

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30

Ning, Hongbo, Junjun Wu, Liuhao Ma, and Wei Ren. "Exploring the pyrolysis chemistry of prototype aromatic ester phenyl formate: Reaction pathways, thermodynamics and kinetics." Combustion and Flame 211 (January 2020): 337–46. http://dx.doi.org/10.1016/j.combustflame.2019.10.002.

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31

Chavan, Sujit P., and Bhalchandra M. Bhanage. "Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source." European Journal of Organic Chemistry 2015, no. 11 (February 27, 2015): 2405–10. http://dx.doi.org/10.1002/ejoc.201500109.

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32

Ferres, Lynn, Halima Mouhib, Wolfgang Stahl, Martin Schwell, and Ha Vinh Lam Nguyen. "Molecular structure and ring tunneling of phenyl formate as observed by microwave spectroscopy and quantum chemistry." Journal of Molecular Spectroscopy 337 (July 2017): 59–64. http://dx.doi.org/10.1016/j.jms.2017.04.017.

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33

Urban, Jiří, Zdeněk Šedivý, Jiří Holubek, Emil Svátek, Miroslav Ryska, Ivan Koruna, Antonín Dlabač, et al. "Potential antidepressants: 1-(2-(Methoxy- and hydroxyphenylthio)phenyl)-2-propylamines." Collection of Czechoslovak Chemical Communications 55, no. 4 (1990): 1077–98. http://dx.doi.org/10.1135/cccc19901077.

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2-(Methoxyphenylthio)benzaldehydes Xa-Xd were reacted with nitroethane in boiling acetic acid to give the corresponding 1-aryl-2-nitropropenes XIIa-XIId; benzonitriles XIIIa and XIIIc and benzaldoximes XXIc and XXId were isolated as by-products. Chromatographed compounds XIIa-XIId were reduced with lithium aluminium hydride to the primary amines VIIa-VIId, and formylated by heating with ethyl formate to the formamides XIVa, XIVc, and XIVd. Reduction of the formamides with lithium aluminium hydride afforded the secondary amines VIIIa, VIIIc, and VIIId, and methylation of the primary amines with formic acid and formaldehyde gave the tertiary amines IXa, IXc, and IXd. Compound VIIIa was prepared also by an alternative route starting from the nitrile XIIIa and proceeding via XIXa and XIVa. Some of the methoxylated amines were demethylated either by heating with pyridine hydrochloride or by treatment with boron tribromide to the title compounds IVa, IVc, Vc, Vd, VIa, and VIc. The amines prepared were transformed to salts for characterization and for pharmacological testing. Compound VIIIa (hydrogen oxalate V⁄FB-15 475) showed clearly the character of a potential antidepressant.

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34

Konishi, Hideyuki, Hiroki Nagase, and Kei Manabe. "ChemInform Abstract: Concise Synthesis of Cyclic Carbonyl Compounds from Haloarenes Using Phenyl Formate as the Carbonyl Source." ChemInform 46, no. 25 (June 2015): no. http://dx.doi.org/10.1002/chin.201525060.

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35

Wang, Haining, Ben Dong, Yang Wang, Jingfu Li, and Yian Shi. "ChemInform Abstract: A Palladium-Catalyzed Regioselective Hydroesterification of Alkenylphenols to Lactones with Phenyl Formate as CO Source." ChemInform 45, no. 23 (May 22, 2014): no. http://dx.doi.org/10.1002/chin.201423125.

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36

Chavan, Sujit P., and Bhalchandra M. Bhanage. "ChemInform Abstract: Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source." ChemInform 46, no. 34 (August 2015): no. http://dx.doi.org/10.1002/chin.201534067.

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37

Oberson, J. M., S. Bénet, K. Redeuil, and E. Campos-Giménez. "Quantitative analysis of vitamin D and its main metabolites in human milk by supercritical fluid chromatography coupled to tandem mass spectrometry." Analytical and Bioanalytical Chemistry 412, no. 2 (December 12, 2019): 365–75. http://dx.doi.org/10.1007/s00216-019-02248-5.

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AbstractA novel method to quantitate vitamin D and its main metabolites (vitamin D3, vitamin D2, and their 25-hydroxy metabolites) in breast milk by supercritical fluid chromatography has been developed and fully validated. A small volume of sample (1 mL) is subjected to ethanolic protein precipitation and liquid-liquid extraction. Final extracts are derivatized with 4-phenyl-1,2,4-triazoline-3,5-dione and vitamin D derivatives analyzed by supercritical fluid chromatography hyphenated to tandem mass spectrometry with atmospheric pressure chemical ionization. Multiple reaction monitoring is used for quantitation. Separation conditions were optimized using a gradient of methanol-water-ammonium formate into carbon dioxide. Make-up solvent was methanol containing ammonium formate. The quantitation limit reached levels as low as 50 pmol/L, with intra- and inter-day relative standard deviations lower than 15% and 20% for all analytes. Accuracy was evaluated by spiking experiments and was well within acceptability ratios (± 15%). The method was then applied to a subset of commercially available human milk samples. The newly developed method provides opportunities to determine the nutritional status of mother-infant dyads from a non-invasive measure, or for interventional or observational studies building knowledge on the composition of human milk.

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38

Ramadan, Doaa R., Francesco Ferretti, and Fabio Ragaini. "Catalytic reductive cyclization of 2-nitrobiphenyls using phenyl formate as CO surrogate: A robust synthesis of 9H-carbazoles." Journal of Catalysis 409 (May 2022): 41–47. http://dx.doi.org/10.1016/j.jcat.2022.03.024.

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39

Ragaini, Fabio, Francesco Ferretti, and Manar Ahmed Fouad. "Phenyl Formate as a CO Surrogate for the Reductive Cyclization of Organic Nitro Compounds to Yield Different N-Heterocycles: No Need for Autoclaves and Pressurized Carbon Monoxide." Catalysts 13, no. 2 (January 18, 2023): 224. http://dx.doi.org/10.3390/catal13020224.

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The reductive cyclization of different organic nitro compounds by carbon monoxide, catalyzed by transition metal complexes, is a very efficient and clean strategy for the synthesis of many N-heterocycles. However, its use requires the use of autoclaves and pressurized CO lines. In this perspective, the authors will present the results obtained in their laboratories on the use of phenyl formate as a convenient CO surrogate, able to liberate carbon monoxide under the reaction conditions and allowing the use of a cheap glass pressure tube as a reaction vessel. In most cases, yields were better than those previously reported by the use of pressurized CO, proving that the use of CO surrogates can be a viable alternative to the gaseous reagent.

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40

Li, Jingfu, Wenju Chang, Wenlong Ren, Wei Liu, Haining Wang, and Yian Shi. "ChemInform Abstract: A Palladium-Catalyzed Enantioselective Hydroesterification of Alkenylphenols with Phenyl Formate. A Facile Approach to Optically Active Dihydrocoumarins." ChemInform 47, no. 9 (February 2016): no. http://dx.doi.org/10.1002/chin.201609168.

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41

Westerhausen, Von Dorothée, Sabine Herrmann, Werner Hummel, and Eberhard Steckhan. "Formate-Driven, Non-Enzymatic NAD(P)H Regeneration for the Alcohol Dehydrogenase Catalyzed Stereoselective Reduction of 4-Phenyl-2-butanone." Angewandte Chemie International Edition in English 31, no. 11 (November 1992): 1529–31. http://dx.doi.org/10.1002/anie.199215291.

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42

Al-Zoubi, Raed M., Khaled T. Jaradat, Walid K. Al-Jammal, and Robert McDonald. "Mild, Efficient, and Highly Regioselective Synthesis of 2,6-Diiodobenzaldehyde Derivatives." Synlett 31, no. 10 (March 20, 2020): 953–58. http://dx.doi.org/10.1055/s-0040-1708004.

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An efficient and versatile synthesis of 2,6-diiodobenzaldehydes via highly regioselective metal–iodine exchange (MIE) of 5-substituted 1,2,3-triiodobenzenes is reported. The nature of substituents (R) on the phenyl has a large influence on the reactivity of reaction but not on the regioselectivity. The regioselectivity of the MIE can be controlled by the use of ethyl formate as a formylating agent providing only the internal benzaldehyde derivatives in excellent site-selectivity. The best reactivity and the highest isolated yields were furnished with products bearing electron-rich substituents. Several chemical transformations of the target compound as a valuable precursor in synthesis were also demonstrated providing the desired derivatives in good isolated yields. This report discloses a protocol for the synthesis of 2,6-diiodobenzaldehyde derivatives that is scalable, general in scope, and indeed difficult to be made by other means.

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43

Kratochvíl, Bohumil, Jiří Novotný, Svatava Smrčková, and Jiří Krechl. "Structure determination of N,N'-diphenylacetamidinium oxalate." Collection of Czechoslovak Chemical Communications 55, no. 2 (1990): 479–84. http://dx.doi.org/10.1135/cccc19900479.

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The structure of N,N'-diphenylacetamidinium oxalate was solved by direct methods and refined anisotropically to R = 0.036 for 1 551 unique observed reflections. The compound (C16H16N2O4) crystallizes in the P21/c space group with the lattice parameters a = 17.672(2), b = 8.263(3), c = 10.771(2) Å, β = 104.64(1)°, Z = 4. Intra- and intermolecular hydrogen bonds between amidinium nitrogens and oxalate oxygens of the N-H···O and O-H···O types form infinite chains parallel to the [010] direction in the structure. Mutual interactions between the chains are mediated by the van der Waals forces. Planes of the phenyl rings bisect at the dihedral angle of 55.8(1)°. In contrast to similar model structures benzamidinium pyruvate, benzamidinium bromoacetate and p-methylbenzamidinium formate monohydrate, the structure of N,N'-diphenylacetamidinium oxalate does not exhibit the amidine-carboxyl interaction through two parallel intramolecular N-H···O bonds.

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Mondal, Koushik, and Rajakumar Balla. "Investigation of kinetics of phenyl radicals with ethyl formate in the gas phase using cavity ring-down spectroscopy and theoretical methodologies." Photochemical & Photobiological Sciences 20, no. 7 (July 2021): 859–73. http://dx.doi.org/10.1007/s43630-021-00053-7.

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Shu-Wen Sun, Li-Xin Meng, and Gao-Feng Wang. "Synthesis and Structural Characterization of a Cobalt Coordination Polymer with Formate and Bis(4-(1H-imidazol-1-yl)phenyl)methanone Ligands." Crystallography Reports 64, no. 7 (December 2019): 1071–74. http://dx.doi.org/10.1134/s1063774519070228.

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46

Kundel, P., and H. Berke. "Chemische Effekte der Nitrosylsubstitution in hexakoordinierten Carbonylwolfram-Verbindungen/ Chemical Effects of Nitrosyl Substitution in Hexacoordinated Carbonyl Tungsten Complexes." Zeitschrift für Naturforschung B 42, no. 8 (August 1, 1987): 993–99. http://dx.doi.org/10.1515/znb-1987-0811.

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AbstractThe reaction of mer-tricarbonyl-nitrosyl-bis(triisopropylphosphite)tungsten hexafluorophosphate (1a) with MeMgl or Bu4NI affords tricarbonyl-iodonitrosyl-(triisopropylphosphite)tungsten (2). Similarly, a carbonyl group of la can be replaced by a fluoride ion resulting in transdicarbonyl- fluoronitrosyl-bis(triisopropylphosphite)tungsten (3). Oxygen nucleophiles like OPh- , OCH3- or OH- either substitute or attack a carbonyl group in la and cause formation of dicarbonyl-nitrosyl-bis(triisopropylphosphite)tungsten phenoxide. methoxide or formate derivatives (4, 5 or 7). respectively. Nitrite ions react with la under CO substitution and bind as nitro ligands to the tungsten center. Addition of equivalent amounts of MeLi, PhLi and NaBH4 to la leads to the formation of tricarbonyl-nitrosyl-(triisopropylphosphite)tungsten methyl and hydrido compounds (8a, 11a) as well as to dicarbonylnitrosyl-bis(triisopropylphosphite)tungsten methyl, phenyl and hydrido complexes (8b, 10 and 11b ) . In the presence of an excess of MeLi., la is transformed to a β-diketonate derivative 9.

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47

Marchei, Emilia, Maria Alias Ferri, Marta Torrens, Magí Farré, Roberta Pacifici, Simona Pichini, and Manuela Pellegrini. "Ultra-High Performance Liquid Chromatography-High Resolution Mass Spectrometry and High-Sensitivity Gas Chromatography-Mass Spectrometry Screening of Classic Drugs and New Psychoactive Substances and Metabolites in Urine of Consumers." International Journal of Molecular Sciences 22, no. 8 (April 13, 2021): 4000. http://dx.doi.org/10.3390/ijms22084000.

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The use of the new psychoactive substances is continuously growing and the implementation of accurate and sensible analysis in biological matrices of users is relevant and fundamental for clinical and forensic purposes. Two different analytical technologies, high-sensitivity gas chromatography-mass spectrometry (GC-MS) and ultra-high-performance liquid chromatography-high-resolution mass spectrometry (UHPLC-HRMS) were used for a screening analysis of classic drugs and new psychoactive substances and their metabolites in urine of formed heroin addicts under methadone maintenance therapy. Sample preparation involved a liquid-liquid extraction. The UHPLC-HRMS method included Accucore™ phenyl Hexyl (100 × 2.1 mm, 2.6 μm, Thermo, USA) column with a gradient mobile phase consisting of mobile phase A (ammonium formate 2 mM in water, 0.1% formic acid) and mobile phase B (ammonium formate 2 mM in methanol/acetonitrile 50:50 (v/v), 0.1% formic acid) and a full-scan data-dependent MS2 (ddMS2) mode for substances identification (mass range 100–1000 m/z). The GC-MS method employed an ultra-Inert Intuvo GC column (HP-5MS UI, 30 m, 250 µm i.d, film thickness 0.25 µm; Agilent Technologies, Santa Clara, CA, USA) and electron-impact (EI) mass spectra were recorded in total ion monitoring mode (scan range 40–550 m/z). Urine samples from 296 patients with a history of opioid use disorder were examined. Around 80 different psychoactive substances and/or metabolites were identified, being methadone and metabolites the most prevalent ones. The possibility to screen for a huge number of psychotropic substances can be useful in suspected drug related fatalities or acute intoxication/exposure occurring in emergency departments and drug addiction services.

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Jaramillo, Rubén D., Beatriz C. Barraza, Alma Polo, Martín Sará, Martha Contreras, and J. Edgardo Escamilla. "The aerobic electron transport system ofEikenella corrodens." Canadian Journal of Microbiology 48, no. 10 (October 1, 2002): 895–902. http://dx.doi.org/10.1139/w02-084.

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The respiratory system of the fastidious β-proteobacterium Eikenella corrodens grown with limited oxygen was studied. Membranes showed the highest oxidase activity with ascorbate plus N,N,N',N'-tetramethyl-p-phenyl enediamine (TMPD) or succinate and the lowest activity with NADH and formate. The presence of a bc1-type complex was suggested by the inhibition exerted by 2-heptyl-4-hydroxyquinoline-N-oxide (HOQNO), myxothiazol, and antimycin A on respiration with succinate and by the effect of the latter two inhibitors on the succinate-reduced difference spectra. Respiration with succinate or ascorbateTMPD was abolished by low KCN concentrations, suggesting the presence of a KCN-sensitive terminal oxidase. Cytochromes b and c were spectroscopically detected after reduction with physiological or artificial electron donors, whereas type a and d cytochromes were not detected. The CO difference spectrum of membranes reduced by dithionite and its photodissociation spectrum (77 K) suggested the presence of a single CO compound that had the spectral features of a cytochrome o-like pigment. High-pressure liquid chromatography analysis of membrane haems confirmed the presence of haem B; in contrast, haems A and O were not detected. Peroxidase staining of membrane type c cytochromes using SDSPAGE revealed the presence of five bands with apparent molecular masses of 44, 33, 30, 26, and 14 kDa. Based on our results, a tentative scheme of the respiratory chain in E. corrodens, comprising (i) dehydrogenases for succinate, NADH, and formate, (ii) a ubiquinone, (iii) a cytochrome bc1, and (iv) a type-cbb' cytochrome c oxidase, is proposed. Key words: Eikenella corrodens, respiratory chain, bc1complex, oxidase cbb'.

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Wani, Dattatraya V., and Santosh N. Mokale. "A Validated Stability-Indicating Liquid Chromatographic Method for the Determination of Lorcaserin and Related Impurities in DRUG Substance Supported by Quality by Design." Journal of Chromatographic Science 58, no. 7 (July 9, 2020): 661–71. http://dx.doi.org/10.1093/chromsci/bmaa034.

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Abstract Lorcaserin (LOR) is selective and potent antiobesity drug that targets the activation of the serotonin 5HT2C receptor. Here a novel, specific, sensitive stability indicating method was developed and validated for the quantitative determination of LOR and its process-related impurities using quality by design principles. By applying experimental design, the authors examine the multifactorial effect of parameters on the critical resolution pair and generated design space representing the robust design. LOR was subjected to stress condition and found stable at all condition, only found significant degradation at oxidative stress condition. The chromatographic separation of degradation product and its process-related impurities were achieved on a Phenomenox Luna phenyl-hexyl column (150 × 4.6 mm × 5 μm), with mobile phase consisting of 10 mM ammonium formate containing 0.1% ammonia solution; pH adjusted to 2.8 with trifluoroacetic acid as solvent A and methanol/acetonitrile (5/95) as solvent B delivered with gradient program at a flow rate of 1.0 mL/min, column temperature was maintained at 25°C and analytes were monitored at 220 nm. The injection volume was 5 μL. The developed RP-LC method was validated and found linear, accurate, specific, selective, precise and robust. The structure of impurities was confirmed by direct mass analysis.

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EL-Atawy, Mohamed A., Dario Formenti, Francesco Ferretti, and Fabio Ragaini. "Synthesis of 3,6-Dihydro-2H-[1, 2]-Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate." ChemCatChem 10, no. 20 (September 13, 2018): 4707–17. http://dx.doi.org/10.1002/cctc.201801223.

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