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Journal articles on the topic 'Grignard compound'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Ravindra, Patil, and Dabade Sapna. "A Review on Grignard Reagent." International Journal of Pharmaceutical Sciences and Medicine 8, no. 4 (2023): 132–42. http://dx.doi.org/10.47760/ijpsm.2023.v08i04.010.

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Grignard reagents are highly reactive organomagnesium halides formed by the reaction of magnesium metal with alkyl or alkenyl halides. They are very strong bases and react with acidic hydrogens such as alcohols, water and carboxylic acids. They are generally produced by reacting an aryl halide or an alkyl halide with magnesium. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound R'−X' in the presence of a suitable catalyst, they typically yield R−R' and the magnesium halide Mg-XX' as a by

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2

Setiawati, Evy, and Khoerul Anwar. "SINTESIS FEROMON 3-METIL 4-OKTANOL SEBAGAI ZAT PEMBASMI HAMA KUMBANG KELAPA Rhynchoporus spp." Jurnal Riset Industri Hasil Hutan 3, no. 2 (2011): 27. http://dx.doi.org/10.24111/jrihh.v3i2.1191.

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The compound of 3-methyl-4-octanol had been synthesized by the formation of Grignard reagent sec-buthyl magnesium bromide. The choosing of reactant 2-bromo butane and n-pentanal were resulted from retrosynthesize analysize of 3-methyl-4octanol pheromone. The reaction of sec-buthyl magnesium bromide was done at temperature 400C for 30 minutes, while the reaction between this reagent with n-pentanal was done for two hours. The formed compound was hydrolized using saturated NH4Cl solution and then cooled. The compound was identified using Infra Red spectrophotometre (IR), Gas Chromatography (GC),

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3

Alesso, Elba N., Liliana M. Finkielsztein, Beatriz Lantaño, Daniel E. Bianchi, Graciela Y. Moltrasio Iglesias, and Jose M. Aguirre. "Synthesis of Diastereoisomeric 1,2,3-Triphenylindans." Australian Journal of Chemistry 50, no. 2 (1997): 149. http://dx.doi.org/10.1071/c95266.

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The stereoisomers of 1,2,3-triphenylindans were synthesized via 1,2,3-triphenylindan-1-ols. The configurational assignments of all the compounds were made by chemical and spectroscopic methods. An unexpected compound was isolated as a by-product of the Grignard reactions and was identified as r-2-hydroxy-2, t-3-diphenylindan-1-one.

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4

Dolliver, Debra D., David B. Delatte, Derek B. Linder, James E. Johnson, Diana C. Canesco, and Jeffrey E. Rowe. "Nucleophilic substitution reactions of N-alkoxyimidoyl fluorides by carbon nucleophiles." Canadian Journal of Chemistry 85, no. 11 (2007): 913–22. http://dx.doi.org/10.1139/v07-097.

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Nucleophilic substitutions of N-alkoxybenzoimidoyl fluorides [p-ClArC(F)=NOR; R = CH3, i-Pr] by enolate-type ions have been performed to produce compounds that can exist in two tautomeric forms: the imine form{p-ClArC(Y)=NOR [Y = CH(CN)2, CH(CN)(CO2Et), CH(CO2Et)2]}or the enamine form {p-ClArC(NHOR)=C(R1)(R2) [R1, R2 = CN, CO2Et]}. These compounds display varying ratios of imine–enamine tautomerizm in chloroform: the diester compound exists almost solely in the imine form, the dicyano compound exists solely in the enamine form, and the cyano-ester compound exists in both tautomeric forms. Comp

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5

Ngoc, Thuc Dinh, Wim Dehaen, Luc Van Meervelt, and Jan Balzarini. "Synthesis of Heterocyclic Triterpene Derivatives with Biological Activities via Click Reaction." Current Organic Chemistry 23, no. 26 (2020): 2969–74. http://dx.doi.org/10.2174/1385272823666191212110411.

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: Grignard reactions were applied to synthesize 2-ethynyl-2-hydroxylallobetulin 5 from 2-oxoallobetulin 4. The compound plays an important role as starting material to synthesize heterocyclic triterpenes using the click reaction. A series of new 1,2,3-triazole derivatives derived from 2-oxoallobetulin were successfully obtained. Under similar reaction conditions, only one compound 6 kept the hydroxyl functional group, while in the other compounds 7, 8 and 9, water was eliminated. The structures of obtained compounds were confirmed by 2D-NMR spectroscopy. The X-ray analysis of 5 indicated that

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6

Wang, Bing-Tao, Hua-Dong Yue, Shu-Ping Luo, Li-Ping Wang, and Dan-Qian Xu. "Diphenyl-5,6,7,7a-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (2007): o1108—o1109. http://dx.doi.org/10.1107/s1600536807004394.

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The title compound, C18H17NO2, synthesized from enantiomerically pure L-proline, methyl chloroformate and a Grignard reagent, crystallizes with two molecules in the asymmetric unit. A chair conformation is adopted by the two fused five-membered rings.

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7

Rajput, Santosh, Valerio Falasca, Mohan Bhadbhade, David StC Black, and Naresh Kumar. "Synthesis and Anticancer Activity of 3,4-Diaryl-1,2-dihydro- and 1,2,3,4-Tetrahydroquinolines." Molecules 29, no. 17 (2024): 4273. http://dx.doi.org/10.3390/molecules29174273.

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Tetrahydroquinolines are key structures in a variety of natural products with diverse pharmacological utilities and other applications. A series of 3,4-diaryl-5,7-dimethoxy-1,2,3,4-tetrahydroquinolines were synthesized in good yield by reacting 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones with different Grignard reagents followed by the dehydration of the intermediate phenolic compounds. Subsequent reduction and deprotection were carried out to achieve the desired tetrahydroquinolone moiety. The lead compound 3c showed low micromolar inhibition of various cancer cell lines. Demethylation un

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8

Kotha, Sambasivarao, Mohammad Saifuddin, Rashid Ali, and Gaddamedi Sreevani. "Spiro annulation of cage polycycles via Grignard reaction and ring-closing metathesis as key steps." Beilstein Journal of Organic Chemistry 11 (August 5, 2015): 1367–72. http://dx.doi.org/10.3762/bjoc.11.147.

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A simple synthetic strategy to C 2-symmetric bis-spiro-pyrano cage compound 7 involving ring-closing metathesis is reported. The hexacyclic dione 10 was prepared from simple and readily available starting materials such as 1,4-naphthoquinone and cyclopentadiene. The synthesis of an unprecedented octacyclic cage compound through intramolecular Diels–Alder (DA) reaction as a key step is described. The structures of three new cage compounds 7, 12 and 18 were confirmed by single crystal X-ray diffraction studies.

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9

Marković, Rade, and Eugen Holzschüh. "Synthesis of Novel n-Alkatrienyltrichlorosilane - Versatile Reagent and Precursor for Organic Monolayer Formation." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 423–26. http://dx.doi.org/10.1135/cccc19960423.

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Preparation of (Z,Z,Z)-9,12,15-octadecatrienyltrichlorosilane (2) by the reaction of the corresponding Grignard reagent with SiCl4 is described. The novel compound of the type RSiX3, useful for various organometallic applications and with the ability to form close-packed ordered monolayers chemically bonded to the surface, was thoroughly characterized by spectral analysis.

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10

Veselý, Zdeněk, Jiří Holubek, and Jan Trojánek. "Reactions in the series of substituted isoindolo[1,2-b][3]-benzazepin-5-ones." Collection of Czechoslovak Chemical Communications 52, no. 1 (1987): 233–41. http://dx.doi.org/10.1135/cccc19870233.

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In the reaction of 10,11-methylenedioxy-3,4,12-trimethoxy-7,8-dihydro-5H-isoindolo[1,2-b][3]-benzazepin-5-one (V) with benzyl alcohol and sodium benzyloxide nucleophilic substitution of the 4-methoxy group for benzyloxy group takes place under formation of 4-benzyloxy-3,12-dimethoxy-10,11-methylenedioxy-7,8-dihydro-5H-isoindolo[1,2-b][3]-benzazepin-5-one (VI). An analogous exchange converts compound V in the presence of corresponding alkoxides and alcohols to compounds VII-X. When reducing compound V with sodium dihydridobis(2-methoxyethoxy)aluminate the unstable base XI is formed which on rea

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11

Abdalrazaq, Sakar M., Afraa S. Shihab, and ,. Iyad S. Hamad. "PREPARATION, CHARACTERIZATION, AND STUDY OF THE BIOLOGICAL ACTIVITY OF 5-CHLORO-8-QUINOLINOL DERIVATIVES AND ITS COORDINATION WITH THE NICKEL (II) AND DIPHOSPHINES." Chemical Problems 22, no. 2 (2024): 157–67. http://dx.doi.org/10.32737/2221-8688-2024-2-157-167.

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Nickel complexes are effective catalysts for cross-coupling reactions between alkyl Grignard reagents and alkenyl–S and alkenyl–Se compounds. In this study, various organic compounds were prepared. Ethylnyl 2-((5-chloro-8-quinolinol)oxy) acetate compound (designated as A1) was synthesized by adding potassium carbonate to quinoline and ethyl chloroacetate. The second compound 2-((5-chloro-8- quinolinol)oxy) acetohydrazide (A2) were obtained by reacting A1with hydrazide. Complex compound A3 were obtained by reacting equimolar amounts of compound A2 with the nickel salt solution, using ethanol as

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12

Šindelář, Karel, Jiří Holubek, Jiří Schlanger, Antonín Dlabač, Martin Valchář, and Miroslav Protiva. "Synthesis of spiro(piperidine-4,6'-dibenz[b,e]-1,4-oxathiepin) and its 1-methyl derivative as potential antidepressant agents." Collection of Czechoslovak Chemical Communications 50, no. 2 (1985): 503–9. http://dx.doi.org/10.1135/cccc19850503.

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Starting from 2-chloronitrobenzene and 2-fluorothiophenol, the synthesis of 2-bromo-2'-fluorodiphenyl sulfide (X) was carried out in three steps. The product was converted to the Grignard reagent which reacted with 1-ethoxycarbonyl-4-piperidone and gave the alcohol XIII. Cyclization of this compound with sodium hydride in dimethylformamide afforded 1-ethoxycarbonylspiro(piperidine-4,6'-dibenz[b,e]-1,4-oxathiepin) (V) which was hydrolyzed to the title compound IV. Reduction of compound V with sodium dihydridobis(2-methoxyethoxy)aluminate afforded the 1-methyl derivative III which exhibited anti

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13

Abualhasan, Murad, Hussein Haider, Ahmad Odeh, and Amer Daraghmeh. "Bioactivity of Synthesized Trifluoromethyl Thioxanthone Analogues." Pharmaceuticals 18, no. 4 (2025): 561. https://doi.org/10.3390/ph18040561.

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Background: The study aims to evaluate the potential of trifluoromethyl thioxanthene derivatives across various biological activities, including antioxidant properties, anti-amylase effects, pancreatic lipase inhibition, anticancer activity, and COX inhibition. This research offers insights into the therapeutic applications of these compounds for managing metabolic disorders and inflammation. Method: Tertiary alcohols were synthesized using Grignard reagents and subsequently combined with L-cysteine, with their structures confirmed via NMR and IR spectroscopy. Results: The results indicated co

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14

Silva, Pedro J., and Carlos E. P. Bernardo. "Unveiling the Reaction Mechanism of the Das/Chechik/Marek Synthesis of Stereodefined Quaternary Carbon Centers." Applied Sciences 11, no. 11 (2021): 5002. http://dx.doi.org/10.3390/app11115002.

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The reaction mechanism of the Cu+-catalyzed introduction of two all-carbon-substituted stereocenters in an ynamide system using a Grignard reagent, a zinc carbenoid, and an aldehyde, was investigated using density-functional theory. In contrast to the formation of an organocopper(I) compound and subsequent carbocupration reaction, previously postulated as the initial step, the reaction proved to instead proceed through an initial complexation of the substrate alkyne bond by the Cu+-catalyst, which primes this bond for reaction with the Grignard reagent. Subsequent addition of the zinc carbenoi

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15

Ertel, Teja Sebastian, Helmut Bertagnolli, Sabine Hückmann, Uwe Kolb, and Dietmar Peter. "XAFS Spectroscopy of Liquid and Amorphous Systems: Presentation and Verification of a Newly Developed Program Package." Applied Spectroscopy 46, no. 4 (1992): 690–98. http://dx.doi.org/10.1366/0003702924125069.

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A program package for XAFS data analysis, especially of liquid and amorphous samples, has been developed. For the first time a consequent error propagation is presented for all functions to be calculated in the course of the data analysis. The structural investigation of the Grignard compound CH3MgBr in diethyl ether is taken as an example for the various steps of the data analysis.

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16

Boyé, O., A. Brossi, H. J. C. Yeh, E. Hamel, B. Wegrzynski, and V. Toome. "Natural products. Antitubulin effect of congeners of N-acetylcolchinyl methyl ether: synthesis of optically active 5-acetamidodeaminocolchinyl methyl ether and of demethoxy analogues of deaminocolchinyl methyl ether." Canadian Journal of Chemistry 70, no. 5 (1992): 1237–49. http://dx.doi.org/10.1139/v92-160.

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Trimethoxy-substituted dihydrodibenzocycloheptenes 4–7, required for a structure–activity study measuring the inhibition of tubulin polymerization in vitro, were synthesized by four different routes: (1) Synthesis of 4 was achieved from 2,3-dimethoxybenzaldehyde via biphenyl aldehyde 17, chain lengthening to propionic acid 20, acid-catalyzed cyclization toward ketone 21, and removal of the carbonyl group. (2) Compound 5 was obtained by eliminating the sterically most hindered methoxy group in 25 or 26 by metal reduction in alcohol. (3) Compound 6 was prepared from biphenyl aldehyde 34 obtained

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17

Mulkapuri, Sateesh, Sathish Kumar Kurapati, and Samar K. Das. "Carbonate encapsulation from dissolved atmospheric CO2 into a polyoxovanadate capsule." Dalton Transactions 48, no. 24 (2019): 8773–81. http://dx.doi.org/10.1039/c9dt01103j.

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A fully reduced polyoxovanadate compound [Na<sub>6</sub>(H<sub>2</sub>O)<sub>24</sub>][H<sub>8</sub>VIV15O<sub>36</sub>(CO<sub>3</sub>)]·3N<sub>2</sub>H<sub>4</sub>·10H<sub>2</sub>O (1) with CO<sub>3</sub><sup>2−</sup> encapsulation in its internal cavity (from dissolved aerial CO<sub>2</sub> in the synthesis reaction mixture) is reported. Compound 1 crystals, on exposure of HCl vapor, excludes carbonate as a CO<sub>2</sub> gas that can be reacted with a Grignard reagent to produce triphenylcarbinol as a major product.

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18

Munguia, Teresita, Ioana S. Pavel, Ramesh N. Kapoor, Francisco Cervantes-Lee, László Párkányi, and Keith H. Pannell. "Lewis acidity of group 14 elements toward intramolecular sulfur in ortho-aryl-thioanisoles." Canadian Journal of Chemistry 81, no. 11 (2003): 1388–97. http://dx.doi.org/10.1139/v03-163.

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The series of compounds (o-CH3SC6H4)CH2EPh3 (E = Si (1), Ge (2), Sn (3), and Pb (4)) have been synthesized and characterized by NMR spectroscopy and by single crystal X-ray diffraction. Compounds 1 and 2 are isostructural with a triclinic crystal system and P-1 space group; however, morphotropic steps occur between Ge and Sn, and Sn and Pb. While the E-S distances in 1 and 2 are 3.985 and 3.974 Å, respectively, ~100% of the sum of the respective van der Waals (vdW) radii, there is a notable distortion from tetrahedral geometry about E. Compound 3 is also triclinic with P-1 symmetry, but has tw

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19

Reddy, B. Siva, and K. R. S. Prasad. "Design, Synthesis and Antibacterial Activity of N-(3-((4-(6-(2,2,2- Trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-yl)amide Derivatives." Asian Journal of Chemistry 33, no. 3 (2021): 577–82. http://dx.doi.org/10.14233/ajchem.2021.23039.

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A new series of N-(3-((4-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-1H-imidazol-2-yl)methyl)oxetan-3- yl)amide derivatives (10a-h)were synthesized by the reaction of 3-((4-(6-(2,2,2-trifluoroethoxy)pyridin- 3-yl)-1H-imidazol-2-yl)methyl)oxetan-3-amine (8) with various carboxylic acids in the presence of T3P catalyst. The reaction is usually furnished within 60 min with good isolated yields. Coupling of 6-(2,2,2-trifluoroethoxy) nicotinic acid (1) with Weinreb amine hydrochloride gave N-methoxy-Nmethyl- 6-(2,2,2-trifluoroethoxy) nicotinamide (2). Compound 3 was synthesized by the Grignard reaction

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20

Seidel, Rüdiger W., Chelladurai Ganesamoorthy, Sinah Loerke, Manuela V. Winter, Christian Gemel та Roland A. Fischer. "catena-Poly[[(tetrahydrofuran-κO)potassium]-μ-(η5:η5)-2,3,4,5-tetramethyl-1-n-pentylcyclopentadienyl]". Acta Crystallographica Section C Crystal Structure Communications 69, № 6 (2013): 573–76. http://dx.doi.org/10.1107/s0108270113011074.

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The title compound, [K(C14H23)(C4H8O)]n, comprises zigzag chains of alternating bridging 2,3,4,5-tetramethyl-1-n-pentylcyclopentadienyl ligands and potassium ions, with an ancillary tetrahydrofuran ligand in the coordination environment of potassium. The coordination polymer strands so formed extend by 21screw symmetry in theb-axis direction. The chemically modified cyclopentadienyl ligand, with a tetheredn-pentyl group, was synthesized from 2,3,4,5-tetramethylcyclopent-2-enone by a Grignard reaction.

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21

Chaitramallu, M1 Devaraju Kesagodu1 Dakshayini Chandrashekarachar2. "SYNTHESIS AND BIOLOGICAL SCREENING OF ANALOGS OF ARYL TETRALONE." INDO AMERICAN JOURNAL OF PHARMACEUTICAL RESEARCH 07, no. 01 (2017): 7392–98. https://doi.org/10.5281/zenodo.1006777.

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The aryl tetralone as potential antimitotic agents were synthesized in four step reactions using Grignard reagent. The first step is the synthesis of trimethoxy phenyl naphthol (2a-f) by the reaction of substituted tetralone with 3, 4, 5-trimethoxy 1-bromobenzene in magnesium metal using tetrahydrofuran as a solvent. The resulted phenyl naphthol was hydrogenated to give phenyl tetralin 3(a-f). The substituted phenyl tetralone were prepared by the oxidation of trimethoxy phenyl tetralin 4(a-f). The structures of the synthesized compounds were confirmed by spectral and elemental analysis data. T

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22

Marsch, Michael, Klaus Harms, Werner Massa та Gernot Boche. "Crystal Structure of theη1-Allyl-Grignard Compound Bis(allylmagnesium chloride-TMEDA)". Angewandte Chemie International Edition in English 26, № 7 (1987): 696–97. http://dx.doi.org/10.1002/anie.198706961.

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23

Yasser N. Mutter AL-Guraby, Ahmed A. S. Alwaaly, and Hassan T. Abdul sahib. "Methylene bis(p-chlorobezodithioate): Synthesis, characterization and its use as analytical reagent for Silver ion." Journal of Kufa for Chemical Sciences 2, no. 9 (2023): 38–55. http://dx.doi.org/10.36329/jkcm/2022/v2.i9.13324.

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The study included the preparation and diagnosis of disulfur ligands (Dithiols) and the preparation of their complex with monovalent (Silver), which included the the following steps: First: preparation of the sulfur compound through the reaction of Grignard reagent (ClPhMgX), with carbon disulfide (CS2), this step form [ClPhCS2]- , an acidic liquid sulfur compound which was converted into a dimer compound by second step :- reacting with (Benzene tetra methyl ammonium hydroxyl) which produce a negatively charged compound [ClPhCS2]-, which is a viscous, hydrated compound with a strong sulfur sme

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24

Micheletti, Mazzacurati, Telese, and Boga. "2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide." Molbank 2020, no. 1 (2020): M1109. http://dx.doi.org/10.3390/m1109.

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2,9-Dimethyl-11-(3-pentadecylphenoxy)dibenzo[c,f][1,2,5]dithiaphosphepine 11-oxide was synthesized (yield 50%) by a two-step procedure. The first step starts with a benzothiadiphosphole and bis-Grignard reagent, and the second step consists of adding the sodium salt of a derivative of cardanol. The structure of newly synthesized compound was elucidated based on 1H-NMR, 13C-NMR, 31P-NMR, IR, Electron Spray Ionization (ESI)–MS, Gas Chromatography-Mass Spectroscopy (GC–MS), and Electron Spray Ionization-High Resolution Mass Spectroscopy (ESI–HRMS).

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25

Metzler, Nils, Heinrich Nöth, Martin Schmidt, and Andreas Treitl. "Die Kristallstrukturen von Magnesiumdibromid-Diglym-Addukten / Crystal Structures of Magnesium Dibromide Diglyme Adducts." Zeitschrift für Naturforschung B 49, no. 10 (1994): 1448–52. http://dx.doi.org/10.1515/znb-1994-1024.

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Abstract(MgBr2·diglyme)2 (1) crystallized in low yield from an ether solution of the Grignard compound mesMgBr (mes = mesityl) on adding diglyme. It is more conveniently prepared from an ether solution of MgBr2 by addition of diglyme. The mixed solvate MgBr2·diglyme thf (2) crystallized from a diglyme/tetrahydrofuran solution of 1 after addition of ether. An X-ray structure determination of 1 reveals dimeric units containing hexacoordinated Mg atoms surrounded by three oxygen atoms and three bromide atoms, with each kind of atoms arranged in a meridional fashion. The two octahedral MgO3Br3 uni

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26

Manuaba, Ida Bagus Putra. "SYNTHESIS, IDENTIFICATION AND IN VITRO ANTITUMOUR PRESCREENING TEST OF TRIPHENYLTIN BENZOATE TOWARDS A HUMAN CERVICAL CARCINOMA CELL LINE, HeLa." Indonesian Journal of Chemistry 8, no. 3 (2010): 418–22. http://dx.doi.org/10.22146/ijc.21599.

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In this study, triphenyltin benzoate was synthesized first, and followed by antitumor prescreening test of the compound towards a human cervical carcinoma cell line, HeLa. Three reaction steps were employed to obtain the compound needed, i.e. 1) synthesizing of tetraphenyltin compound via insitu phenilmagnesiumbromide Grignard reaction to tin(IV)chloride, 2) synthesizing triphenyltin chloride via redistribution reaction of tetraphenyltin to tin(IV) chloride without any solvent, the reaction completed depends on the temperature, in this case a good results was achieved at temperature 220 °C for

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27

Dietzel, Pascal D. C., and Martin Jansen. "Synthesis and Crystal Structure of Tris- [3,5-bis(trifluoromethyl)phenyl]arsine." Zeitschrift für Naturforschung B 59, no. 3 (2004): 345–47. http://dx.doi.org/10.1515/znb-2004-0320.

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The title compound, As[C6H3(CF3)2]3, has been synthesised by Grignard reaction from arsenic trichloride and 3,5-bis(trifluoromethyl)phenylmagnesium bromide. It crystallises in the triclinic space group P1̅ with two formula units in the asymmetric unit. The most prominent feature of the crystal structure is the protrusion of a phenyl group of one molecule into the cavity at the base of the pyramid of a second molecule. The crystal structure is then built up by densely packing these units of interlocked molecules to form columns, which are arranged in parallel in a distorted hexagonal pattern

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28

Stevens, Matthew P., Emily Spray, Iñigo J. Vitorica-Yrezabal, et al. "Structural Investigation of Magnesium Complexes Supported by a Thiopyridyl Scorpionate Ligand." Molecules 27, no. 14 (2022): 4564. http://dx.doi.org/10.3390/molecules27144564.

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Herein, we report the synthesis of a series of heteroleptic magnesium complexes stabilized with the scorpionate ligand tris(2-pyridylthio)methanide (Tptm). The compounds of the general formula [Mg(Tptm)(X)] (1-X; X = Cl, Br, I) were obtained via protonolysis reaction between the proligand and selected Grignard reagents. Attempts to isolate the potassium derivative K(Tptm) lead to decomposition of Tptm and formation of the alkene (C5H4N-S)2C=C(C5H4N-S)2, and this degradation was also modelled using DFT methods. Compound 1-I was treated with K(CH2Ph), affording the degradation product [Mg(Bptm)2

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29

Shen, Kao-Hsien, Chun-Wei Kuo, and Ching-Fa Yao. "An efficient of Grignard-type procedure for the preparation of gem-diallylated compound." Tetrahedron Letters 48, no. 36 (2007): 6348–51. http://dx.doi.org/10.1016/j.tetlet.2007.07.008.

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30

Liu, Xu Ying, Yu Jiang, Wen Guang Wang, and Jia Ling Pu. "Odd-Carbon Alkyl-Substituent Effect on Liquid Crystalline Properties of Discotic Hexa-Peri-Hexabenzocoronene Molecule." Advanced Materials Research 239-242 (May 2011): 3358–61. http://dx.doi.org/10.4028/www.scientific.net/amr.239-242.3358.

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Hexa-peri-Hexabenzocoronene (HBC), as the smaller graphene fragment consisting of 13 fused benzene rings, possesses a strong tendency to stack together via π-electronic interaction. In this paper, the 1,2-(4-bromomethyl-1-yl) acetylene was alkylated by Grignard reagent to form corresponding 1,2-bis(p-pentadecanylphenyl)acetylene. Cobalt(0)-catalyzed cyclotrimerization was carried out to give hexaphenylbenzene analogue. This step was followed by intramolecular cyclodehydrogenation to yield the desired product HBC-C15. The identity and purity of the new compound was confirmed by UV-vis spectrome

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31

Yin, Guo-Jie, Gang-Bin Yang, and Shi-Min Wang. "9-Phenyl-4,5-diaza-9H-fluoren-9-ol monohydrate." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1817. http://dx.doi.org/10.1107/s1600536812021940.

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The title compound, C17H12N2O·H2O, was synthesized by the reaction of 4,5-diazafluoren-9-one with a Grignard reagent in ether (the reaction mixture being hydrolysed with saturated NH4Cl solution), and crystallizes with two organic molecules and two water molecules in the asymmetric unit. The 4,5-diazafluorene fragment is approximately planar, with r.m.s. deviations of 0.0448 and 0.0198 Å in the two molecules. The dihedral angles between the 4,5-diazafluorene planes and the phenyl ring are 80.49 (6) and 76.57 (7)°. The crystal packing features O—H...N and O—H...O hydrogen bonds involving the br

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32

HARDEO, N. SINGH, and PRASAD SINGH RAMAYAN. "A New Synthesis of a Naturally Occurring lsocoumarin. 3,4-Dimethyl-8-hydroxyisocoumarin (Oospolactone)." Journal of Indian Chemical Society Vol. 65, Oct 1988 (1988): 685–87. https://doi.org/10.5281/zenodo.6076346.

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Department of Chemistry, Bhagalpur University, Bhagalpur-812 007 <em>Manuscript received 13 May 1988, accepted 8 July 1988</em> 3,4-Dimethyl-8-methoxyisochroman (5a) on oxidation furnishes 3,4-dimethyl-8- methoxy-3,4-dihydroisocoumarin (6a), and demethylated with hydriodic acid to 3,4- dimethyl-8-hydroxy-3,4-dihydroisocoumarin (7a). Treatment of 6a with<em> N</em>-bromosuccinimide followed by refluxing with triethylamine furnishes 3 4-dimethyl-8-methoxyisocoumarin (8a) which on demethylation with hydriodic acid yields 3,4-dimethyl-8-hydroxyisocoumarin (oospolactone) (9a) Compound 5a and 3,4-dl

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33

Sivakrishna, Balija, Sehbanul Islam, Amarendra Panda, Maddi Saranya, Manas K. Santra, and Shantanu Pal. "Synthesis and Anticancer Properties of Novel Truncated Carbocyclic Nucleoside Analogues." Anti-Cancer Agents in Medicinal Chemistry 18, no. 10 (2019): 1425–31. http://dx.doi.org/10.2174/1871520618666180322120533.

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Background: Modified nucleosides established a prime role as therapeutic drugs. Objective: Design and synthesis of novel truncated carbocyclic nucleoside with modified nucleobases and evaluation of their anticancer properties. Methods: Novel truncated carbocyclic nucleoside analogues were synthesized from a versatile starting material D-ribose. The synthetic route includes stereoselective Grignard reaction, Wittig olefination, ring closing metathesis, double bond hydrogenation and Mitsunobu nucleobase condensation as the key steps. Cytotoxicity was measured using MTT assay in breast cancer cel

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34

Bélanger, Patrice C., and Claude Dufresne. "Preparation of exo-6-benzyl-exo-2-(m-hydroxyphenyl)-1-dimethylaminomethylbicyclo[2.2.2.]octane. A non-peptide mimic of enkephalins." Canadian Journal of Chemistry 64, no. 8 (1986): 1514–20. http://dx.doi.org/10.1139/v86-248.

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A model for the active conformation of methionine enkephalin was derived from computer modeling. From this model, a target was designed and synthesized using bicyclo[2.2.2]octane as a structural template. Thus, a key intermediate, exo-6-benzoyl-1-carboethoxybicyclo[2.2.2]-2-octene was prepared via a Diels–Alder reaction using ethyl dihydrobenzoate and phenylvinylketone. It was subsequently modified to exo-6-benzyl-1-dimethylaminobicyclo[2.2.2]-2-octene. This intermediate was hydroborated and oxidized to the ketone on which the second aromatic group was introduced using a Grignard reaction, eve

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35

Barbosa, Luiz Cláudio de A., Gelson J. A. Conceição, Antônio J. Demuner, Antônio A. Silva, John Mann, and Dorila Piló-Veloso. "A New Class of Herbicides that are Derivatives of 8-Oxabicyclo[3.2.1]oct-6-en-3-one." Australian Journal of Chemistry 52, no. 10 (1999): 929. http://dx.doi.org/10.1071/ch99044.

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Treatment of 8-oxabicyclo[3.2.1]oct-6-en-3-one with a catalytic amount of osmium tetraoxide and excess hydrogen peroxide resulted in the formation of the acetonide exo-6,exo-7-isopropylidenedioxy-8-oxabicyclo[3.2.1]oct-3-one (2), in 96% yield. This acetonide was converted into several aromatic alcohols (4a–k) through a Grignard reaction. The alcohols were treated with aqueous HCl in acetone, and the corresponding alkenes (5a–c,e–g, j,k) were obtained in 26–46% overall yield, from the ketone (2). The herbicidal activity of the alkenes was evaluated at a concentration of 6.6 µg g−1. All compound

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36

Lombardo, Marco, Sebastiano Licciulli, and C. Trombini. "3-Halopropenyl esters as precursors of a new class of oxygen-substituted allylic organometallic compounds: Applications in organic synthesis." Pure and Applied Chemistry 76, no. 3 (2004): 657–69. http://dx.doi.org/10.1351/pac200476030657.

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3-halopropenyl esters, readily prepared by the addition of acyl halides to acrolein, react with zinc, indium, and chromium(II), thus opening a route to a new class of oxygen-substituted allylic organometallic compounds. Indium and zinc reagents smoothly add to carbonyl compounds, affording alk-1-en-3,4-diol derivatives in a variety of synthetic procedures which include typical Grignard stepwise conditions as well as Barbier one-pot protocols. Using zinc and indium in water or aprotic solvents, simple diastereoselectivity was found to depend on the nature of the carbonyl compound; conjugated al

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37

Lindner, Ekkehard, and Christoph Scheytt. "Neuartige basische Liganden für die homogenkatalytische Homologisierung von Methanol zu Ethanol, IV [1] Synthese, Eigenschaften und NMR-spektroskopische Untersuchungen von mehrzähnigen Furfurylphosphanen / Novel Basic Ligands for the Homogeneous Catalytic Homologation of Methanol to Ethanol, IV [1] Synthesis, Properties and NMR Spectroscopic Investigations on Polydentate Furfurylphosphanes." Zeitschrift für Naturforschung B 41, no. 1 (1986): 10–17. http://dx.doi.org/10.1515/znb-1986-0104.

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The furfurylphosphonium salts [RP(CH2C4H2O3]Br (2a-c, e, f) [R = Ph (a). Mes (b). Me (c), t-Bu (e), CH7C4H3O (f)] and [Ph2P(CH2C4H3O)2]Br (6) are obtained by reaction of the silvlphosphanes RP(SiMe3)2 (1a-c, e). P(SiMe3), (3) and Ph2PSiMe3 (5) with BrCH2C4H3O (eq. (1). (2) and (5)). In THF 2a-c, e, f and 6 are degraded by LiAlH4 to give the tri- and bidentate alkyl and aryl furfurylphosphanes RP(CH2C4H3O)2 (4a-c, e, f) and Ph2PCH2C4H3O (7). respectively (eq. (3) and (5)). The formation of EtP(CH2C4H3O)2 (4d) succeeds via degradation of the phosphonium salt [EtP(CH2C4H3O)3]I (2d) which results

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38

Clemente, Francesca, Macarena Martínez-Bailén, Camilla Matassini та ін. "Synthesis of a New β-Galactosidase Inhibitor Displaying Pharmacological Chaperone Properties for GM1 Gangliosidosis". Molecules 27, № 13 (2022): 4008. http://dx.doi.org/10.3390/molecules27134008.

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GM1 gangliosidosis is a rare lysosomal disease caused by the deficiency of the enzyme β-galactosidase (β-Gal; GLB1; E.C. 3.2.1.23), responsible for the hydrolysis of terminal β-galactosyl residues from GM1 ganglioside, glycoproteins, and glycosaminoglycans, such as keratan-sulfate. With the aim of identifying new pharmacological chaperones for GM1 gangliosidosis, the synthesis of five new trihydroxypiperidine iminosugars is reported in this work. The target compounds feature a pentyl alkyl chain in different positions of the piperidine ring and different absolute configurations of the alkyl ch

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39

Wegner, Gerald L., Raphael J. F. Berger, Annette Schier, and Hubert Schmidbaur. "Generation of Bis[2,6-di(4-methoxy-phenyl)phenyl]plumbylene and its Insertion into n-Butyliodide to Give a Tetrahedral Triorganolead(IV) Iodide." Zeitschrift für Naturforschung B 55, no. 11 (2000): 995–99. http://dx.doi.org/10.1515/znb-2000-1101.

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1 -Iodo-2,6-bis(4-methoxy-phenyl)benzene (BipapI) was prepared in a Grignard reaction from 4-bromo-anisol and 2,6-dibrom o-1 -iodo-benzene in tetrahydrofuran (61% yield). Treatment of BipapI with Az-butyllithium in hexane/diethylether gave the corresponding terphenyl-lithium compound BipapLi which crystallized as the dietherate in 83% yield. The structure of BipapLi • (OE2)2 has been determined by single crystal X-ray methods. The molecule is a monomer in the lattice, and the lithium atom is three-coordinate. Preparation of BipapLi in the presence of PbCl2 in diethylether gave a green solution

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40

WALBORSKY, H. M. "ChemInform Abstract: How a Grignard Compound is Formed. The Signicant Influence of the Metal Surface." ChemInform 22, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199134305.

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41

Drandarov, Konstantin, and Willi Kantlehner. "Orthoamides and Iminium Salts, LXXX [1]. C-Glycosyl Alkynecarboxylic Acid Orthoamides. Versatile Intermediates in the Synthesis of New Types of Highly Substituted C-Nucleoside Analogs." Zeitschrift für Naturforschung B 67, no. 7 (2012): 699–716. http://dx.doi.org/10.5560/znb.2012-0108.

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The C-glycosyl alkynecarboxylic acid orthoamides 22 and 23 are proposed as versatile precursors for the synthesis of new types of C-nucleoside analogs. The new synthetic strategy includes alkynylation of protected aldoses 13 or ketoses by Grignard ethynylation or Barbier propargylation, O-protection of the resulting alkynols 14-16, and nucleophilic addition of the metalated protected terminal alkynes 20 and 21 to peralkylguanidinium salt 2 to afford the corresponding alkynecarboxylic acid orthoamides 22 and 23, which in reactions with mono or bis-nucleophiles could serve as building blocks for

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42

Hogenbirk, Marijke, Gerrit Schat, Otto S. Akkerman, Friedrich Bickelhaupt, Wilberth J. J. Smeets, and Anthony L. Spek. "The first x-ray structure of a 1,1-di-Grignard compound: bis(bromomagnesio)bis(trimethylsilyl)methane." Journal of the American Chemical Society 114, no. 18 (1992): 7302–3. http://dx.doi.org/10.1021/ja00044a056.

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43

Boeré, René T., and Jason D. Masuda. "2,6-Diisopropylphenylphosphane: A new, bulky primary phosphane and its mono- and disilylated Si(CH3)3 and Si(CH3)2-t-Bu derivatives A synthetic, crystallographic, and dynamic NMR investigation." Canadian Journal of Chemistry 80, no. 11 (2002): 1607–17. http://dx.doi.org/10.1139/v02-150.

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The bulky primary phosphane 2,6-diisopropylphenylphosphane, DipPH2, has been prepared from 1-bromo-2,6-diisopropylbenzene via the reaction of the Grignard reagent with PCl3. The resulting mixed phosphonous dihalides DipP(Cl,Br)2 are reduced with LiAlH4 to yield the title compound in reasonable yield and on a synthetically useful scale. DipPH2 is also used to prepare the monosilylated derivatives DipPHSi(CH3)3 and DipPH{Si(CH3)2-t-Bu} as well as the disilylated compounds DipP{Si(CH3)3}2 and DipP{Si(CH3)2-t-Bu}2. All products have been fully characterized by IR, mass, and NMR spectroscopy. The c

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44

Vollet, Jean, Jens R. Hartig, Katarzyna Baranowska, and Hansgeorg Schnöckel. "The Anion [Mg6Cl8Cp*5]-: A Final Intermediate on the Way to the Molecular Donor-Free Grignard Compound MgClCp*?" Organometallics 25, no. 8 (2006): 2101–3. http://dx.doi.org/10.1021/om051074s.

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45

HOGENBIRK, M., G. SCHAT, O. S. AKKERMAN, F. BICKELHAUPT, W. J. J. SMEETS, and A. L. SPEK. "ChemInform Abstract: The First X-Ray Structure of a 1,1-Di-Grignard Compound: Bis( bromomagnesio)bis(trimethylsilyl)methane." ChemInform 23, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199249050.

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46

Riedmiller, Frank, Alexander Jockisch, and Hubert Schmidbaur. "Synthesis and Molecular Structures of 2-Trimethylsilyl-, 2-Trimethylgermyl-, and 2-Trimethylstannyl-pyridines." Zeitschrift für Naturforschung B 54, no. 1 (1999): 13–17. http://dx.doi.org/10.1515/znb-1999-0105.

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5-Methyl-2-trimethylsilyl-pyridine (1) has recently been prepared via the “in situ” Grignard reaction of 1-bromo-5-methyl-pyridine with magnesium and trimethylchlorosilane in refluxing tetrahydrofuran (thf) and structurally characterized. 2-Trimethylgermyl- (2) and 2- trimethylstannyl-pyridine (3) were now obtained from 2-bromo-pyridine through metallation (with n-BuLi) and treatment of the intermediates with Me3GeBr and Me3SnCl, respectively, in diethylether/ thf at -70°C. The crystal and molecular structure of compound 2 has been determined by low temperature (in situ) single crystal X-ray d

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47

Hamdan, Azni Izwati, Dike Dandari Sukmana, and Norsyafikah Asyilla Nordin. "SYNTHESIS AND BIOLOGICAL ACTIVITIES OF ACETAMINOPHEN AND IBUPROFEN METAL COMPLEXES OR DERIVATIVES: A REVIEW." Malaysian Journal of Science 43, no. 1 (2024): 86–112. http://dx.doi.org/10.22452/mjs.vol43no1.8.

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We reviewed scientific literature on the synthesis of acetaminophen and ibuprofen, as well as their derivatives and biological properties. The synthesis of acetaminophen involves the acetylation of 4-aminophenol and acetic anhydride, while ibuprofen is synthesised by reacting isobutyl benzene and acetic anhydride in four continuous reaction stages, which are Friedel-Crafts acylation, carbonyl reduction, chloride substitution, and Grignard reaction. To obtain their derivatives, modifications have been made either by complexing the main structure of the drug compound with metal elements or addin

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48

Kruczyński, T., F. Henke, M. Neumaier, K. H. Bowen, and H. Schnöckel. "Many Mg–Mg bonds form the core of the Mg16Cp*8Br4K cluster anion: the key to a reassessment of the Grignard reagent (GR) formation process?" Chemical Science 7, no. 2 (2016): 1543–47. http://dx.doi.org/10.1039/c5sc03914b.

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It caused a sensation eight years ago, when the first room temperature stable molecular compound with a Mg–Mg bond (LMgMgL, L = chelating ligand) containing magnesium in the oxidation state +1 was prepared.

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49

Klein, Hans Friedrich, Herbert Koenig, Susanne Koppert, Klaus Ellrich, and Juergen Riede. "Cobalt diazenides of Main Group 1-3 metals: X-ray structure of a Grignard compound containing (dinitrogen)(trimethylphosphine)cobaltate anions." Organometallics 6, no. 6 (1987): 1341–45. http://dx.doi.org/10.1021/om00149a034.

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50

Mori, Toshifumi, and Shigeki Kato. "Grignard Reagents in Solution: Theoretical Study of the Equilibria and the Reaction with a Carbonyl Compound in Diethyl Ether Solvent." Journal of Physical Chemistry A 113, no. 21 (2009): 6158–65. http://dx.doi.org/10.1021/jp9009788.

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