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Journal articles on the topic 'Benzylic derivatives'

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Published: 8 June 2024

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1

Loska, Rafał, Mieczysław Mąkosza, and Kacper Kisiel. "Synthesis of Aryloxiranes and Arylcyclopropanes via Deprotonation of Benzyl Chlorides." Synthesis 54, no. 09 (February 21, 2022): 2289–97. http://dx.doi.org/10.1055/s-0040-1719895.

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AbstractUpon the action of strong bases at low temperature, benzyl chloride and its ring-substituted derivatives undergo deprotonation at the benzylic position and the produced carbanions react with aldehydes, ketones and Michael acceptors to form aryl oxiranes and cyclopropanes.
2

Khan, Ajmir, Mohammed G. Sarwar, and Sher Ali. "Reactivity and Stability of (Hetero)Benzylic Alkenes via the Wittig Olefination Reaction." Molecules 29, no. 2 (January 19, 2024): 501. http://dx.doi.org/10.3390/molecules29020501.

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Wittig olefination at hetero-benzylic positions for electron-deficient and electron-rich heterocycles has been studied. The electronic effects of some commonly used protective groups associated with the N-heterocycles were also investigated for alkenes obtained in the context of the widely employed Wittig olefination reaction. It was observed that hetero-benzylic positions of the pyridine, thiophene and furan derivatives were stable after Wittig olefination. Similarly, electron-withdrawing groups (EWGs) attached to N-heterocycles (indole and pyrrole derivatives) directly enhanced the stability of the benzylic position during and after Wittig olefination, resulting in the formation of stable alkenes. Conversely, electron-donating group (EDG)-associated N-heterocycles boosted the reactivity of benzylic alkene, leading to lower yields or decomposition of the olefination products.
3

Bi, Xian-Jun, Luke T. Higham, Janet L. Scott, and Christopher R. Strauss. "Reactions of 2,6-Dibenzylidenecyclohexanone and its Derivatives in High-Temperature Water." Australian Journal of Chemistry 59, no. 12 (2006): 883. http://dx.doi.org/10.1071/ch06381.

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The reactivity of derivatives of 2,6-dibenzylidenecyclohexanone was investigated in water at 220–250°C under microwave conditions, without added catalyst. Retro-Claisen–Schmidt processes predominated. Hydrolytic attack at the benzylic position afforded a 2-benzylidenecyclohexanone derivative and liberated an aryl aldehyde. Dienones substituted with electron-withdrawing or -donating groups on the aryl rings were more susceptible to hydrolysis than was the parent 2,6-dibenzylidenecyclohexanone.
4

Kikuchi, Jun, Shota Kodama, and Masahiro Terada. "Radical addition reaction between chromenols and toluene derivatives initiated by Brønsted acid catalyst under light irradiation." Organic Chemistry Frontiers 8, no. 15 (2021): 4153–59. http://dx.doi.org/10.1039/d1qo00657f.

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A Brønsted acid-catalyzed radical addition reaction between chromenols and toluene derivatives was accomplished under light irradiation, affording benzylated chromene derivatives through benzylic C(sp3)–H functionalization of toluene derivatives.
5

Patil, Pravin, and Frederick Luzzio. "Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues." Synlett 28, no. 14 (July 24, 2017): 1729–32. http://dx.doi.org/10.1055/s-0036-1588510.

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A novel tert-butyl 2-(1-oxoisoindolin-2-yl)acetate derivative is selectively alkylated with propargyl bromide in the presence of lithium hexamethyldisilazide. After removal of the tert-butyl protecting group, the resulting N-isoindolinyl (ethynylalanine) derivative is reacted with a series of azides under ‘click conditions’. The click reactions afford an array of N-isoindolinyl- 1,2,3-triazolylalanine derivatives as the free carboxylic acids. Following esterification, the N-isoindolinone protecting group is then transformed into the more easily removable phthaloyl group by selective oxidation at the benzylic position.
6

Yi, Hong, Changliang Bian, Xia Hu, Linbin Niu, and Aiwen Lei. "Visible light mediated efficient oxidative benzylic sp3 C–H to ketone derivatives obtained under mild conditions using O2." Chemical Communications 51, no. 74 (2015): 14046–49. http://dx.doi.org/10.1039/c5cc06015j.

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A photooxygenation of benzylic sp3 C–H reaction has been demonstrated using O2 mediated by visible light. Various benzylic sp3 C–H bonds can be transformed into the desired ketone derivatives in moderate to good yields.
7

Ellwart, Mario, Georg Höfner, Aaron Gerwien, Klaus Wanner, and Paul Knochel. "Synthesis and Bioactivity of Novel N-Benzylic and N-Phenethylic Ephedrine Derivatives." Synthesis 49, no. 23 (August 23, 2017): 5159–66. http://dx.doi.org/10.1055/s-0036-1588523.

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A range of N-benzylic and N-phenethylic ephedrine derivatives were prepared in a one-pot procedure starting from the two enantiomers of ephedrine using the Potier reagent, and a polyfunctional aryl- or benzylic organozinc halide. The biological activity in indatraline MS Binding Assays addressing hDAT, hNET and hSERT was determined and discussed.
8

Egami, Hiromichi, Takafumi Ide, Yuji Kawato, and Yoshitaka Hamashima. "Benzylic C–H trifluoromethylation of phenol derivatives." Chemical Communications 51, no. 93 (2015): 16675–78. http://dx.doi.org/10.1039/c5cc07011b.

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Phenol derivatives were trifluoromethylated using copper/Togni reagent. Reaction in DMF selectively gave benzylic trifluoromethylation products, whereas aromatic trifluoromethylation products were obtained in t-BuOH.
9

Pereira, Raul, Lukas Pfeifer, Jean Fournier, Véronique Gouverneur, and Ján Cvengroš. "Twisting the ethano-Tröger's base: the bisamide." Organic & Biomolecular Chemistry 15, no. 3 (2017): 628–33. http://dx.doi.org/10.1039/c6ob02359b.

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10

Knochel, Paul, and Alicia Castelló-Micó. "Zincation and Magnesiation of Functionalized Silylated Cyano­hydrins Using TMP-Bases." Synthesis 50, no. 01 (August 24, 2017): 155–69. http://dx.doi.org/10.1055/s-0036-1590887.

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Polyfunctional silylated cyanohydrins are readily magnesiated or zincated with TMPMgCl·LiCl or TMP2Zn·2MgCl2·2LiCl leading to the corresponding metallated derivatives. These Mg- or Zn-derivatives react with various electrophiles such as benzylic bromides, allylic bromides, acid chlorides, aldehydes, NCCO2Et, or MeSO2SMe. Subsequently, TBAF-deprotection provides the corresponding keto or 1,2-diketo derivatives.
11

Hoang, G. L., S. Zhang, and J. M. Takacs. "Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides." Chemical Communications 54, no. 38 (2018): 4838–41. http://dx.doi.org/10.1039/c8cc01563e.

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12

Yoshida, Taira, and Keiji Mori. "Hf(OTf)4-Catalyzed highly diastereoselective synthesis of 1,3-disubstituted tetralin derivatives via benzylic C(sp3)–H bond functionalization." Chemical Communications 53, no. 31 (2017): 4319–22. http://dx.doi.org/10.1039/c7cc01717k.

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13

Croft, Anna K., and Christopher J. Easton. "Anchimeric Assistance in Hydrogen-Atom Transfer to Bromine." Australian Journal of Chemistry 57, no. 7 (2004): 651. http://dx.doi.org/10.1071/ch04058.

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The free-radical benzylic brominations of series of phenylalanine derivatives and O-phenylalkyl benzoates and N-phenylalkylamides with N-bromosuccinimide exhibit anchimeric assistance by neighbouring ester and amido groups. Rate enhancement occurs through electron donation to the electropositive carbon centre that develops in the transition state of the hydrogen-atom transfer to bromine. The extent of the effect depends on the electron demand at the benzylic position and the electron-donating ability of the neighbouring group.
14

Mani, Geeta Sai, Kavitha Donthiboina, Nagula Shankaraiah, and Ahmed Kamal. "Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds via sp3 C–H functionalization of azaarenes." New Journal of Chemistry 43, no. 40 (2019): 15999–6006. http://dx.doi.org/10.1039/c9nj03573g.

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15

Wang, Zhonglei, and Liansuo Zu. "Organocatalytic enantioselective direct alkylation of phloroglucinol derivatives: asymmetric total synthesis of (+)-aflatoxin B2." Chemical Communications 55, no. 35 (2019): 5171–74. http://dx.doi.org/10.1039/c9cc01833f.

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The organocatalytic enantioselective Friedel–Crafts alkylation of the phloroglucinol derivatives with enals is reported, providing general access to the benzylic chiral centers shown in a variety of phloroglucinol natural products.
16

Hug, Joachim J., Louise Kjaerulff, Ronald Garcia, and Rolf Müller. "New Deoxyenhygrolides from Plesiocystis pacifica Provide Insights into Butenolide Core Biosynthesis." Marine Drugs 20, no. 1 (January 14, 2022): 72. http://dx.doi.org/10.3390/md20010072.

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Marine myxobacteria present a virtually unexploited reservoir for the discovery of natural products with diverse biological functions and novel chemical scaffolds. We report here the isolation and structure elucidation of eight new deoxyenhygrolides (1–8) from the marine myxobacterium Plesiocystis pacifica DSM 14875T. The herein described deoxyenhygrolides C–J (1–8) feature a butenolide core with an ethyl residue at C-3 of the γ-lactone in contrast to the previously described derivatives, deoxyenhygrolides A and B, which feature an isobutyl residue at this position. The butenolide core is 2,4-substituted with a benzyl (1, 2 and 7), benzoyl (3 and 4) or benzyl alcohol (5, 6 and 8) moiety in the 2-position and a benzylidene (1–6) or benzylic hemiketal (7 and 8) in the 4-position. The description of these new deoxyenhygrolide derivatives, alongside genomic in silico investigation regarding putative biosynthetic genes, provides some new puzzle pieces on how this natural product class might be formed by marine myxobacteria.
17

Blangetti, Marco, Patricia Fleming, and Donal F. O'Shea. "Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes." Beilstein Journal of Organic Chemistry 7 (September 9, 2011): 1249–54. http://dx.doi.org/10.3762/bjoc.7.145.

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A new two-step general approach to [2.2]metacyclophane synthesis from substituted m-xylenes is described. The strategy employs a selective benzylic metalation and oxidative C–C bond formation for both synthetic operations. Regioselective benzylic metalation is achieved using the BuLi, KOt-Bu, TMP(H) (2,2,6,6-tetramethylpiperidine) combination (LiNK metalation conditions) and oxidative coupling with 1,2-dibromoethane. The synthetic ease of this approach compares favourably with previously reported methods and allows for ready access to potentially useful planar chiral derivatives.
18

Chen, Hongbiao, Litao Shen, and Yuanbin Lin. "Benzylic Bromination of Toluene Derivatives with Boron Tribromide." Synthetic Communications 40, no. 7 (March 4, 2010): 998–1003. http://dx.doi.org/10.1080/00397910903029917.

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19

Cámpora, Juan, Enrique Gutiérrez, Manuel L. Poveda, Caridad Ruíz, and Ernesto Carmona. "Binuclear σ- and η3-benzylic derivatives of nickel." J. Chem. Soc., Dalton Trans., no. 11 (1992): 1769–74. http://dx.doi.org/10.1039/dt9920001769.

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20

Chen, Long, Yun-Xiang Zou, Xin-Yue Fang, Jie Wu, and Xiao-Hua Sun. "Brønsted acid-catalysed regiodivergent phosphorylation of 2-indolylmethanols to synthesize benzylic site or C3-phosphorylated indole derivatives." Organic & Biomolecular Chemistry 16, no. 40 (2018): 7417–24. http://dx.doi.org/10.1039/c8ob02033g.

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A Brønsted acid catalyzed highly regiodivergent phosphorylation of 2-indolylmethanols with diarylphosphine oxides has been established, which provides an efficient protocol for accessing benzylic site or C3-phosphorylated indole derivatives with structural diversity.
21

Bettoni, Marta, Tiziana Del Giacco, Cesare Rol, and Giovanni V. Sebastiani. "“Dark” Adsorption Equilibrium Constants of Benzylic Derivatives on TiO2 and Their Implications in the Sensitised Heterogeneous Photooxidation." Journal of Chemical Research 2003, no. 7 (July 2003): 415–17. http://dx.doi.org/10.3184/030823403103174344.

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The “dark” adsorption equilibrium constants of different series of benzylic derivatives on TiO2 suspended in CH3CN were determined through a Langmuir-type adsorption isotherm. In particular, the similarity of the K values of differently ring substituted α-OH derivatives within the same series confirms the previously suggested preferential adsorption of the hydroxyl group (at the oxygen atom) with respect to the aromatic moiety.
22

Samzadeh-Kermani, A. "Synthesis of benzyl hydrazine derivatives via amination of benzylic C(sp3)–H bonds with dialkyl azodicarboxylates." New Journal of Chemistry 42, no. 6 (2018): 4766–72. http://dx.doi.org/10.1039/c7nj04880g.

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23

Ticconi, Barbara, Arianna Colcerasa, Stefano Di Stefano, Osvaldo Lanzalunga, Andrea Lapi, Marco Mazzonna, and Giorgio Olivo. "Oxidative functionalization of aliphatic and aromatic amino acid derivatives with H2O2 catalyzed by a nonheme imine based iron complex." RSC Advances 8, no. 34 (2018): 19144–51. http://dx.doi.org/10.1039/c8ra02879f.

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24

Kato, Terumasa, and Keiji Maruoka. "Selective functionalization of benzylic C–H bonds of two different benzylic ethers by bowl-shaped N-hydroxyimide derivatives as efficient organoradical catalysts." Chemical Communications 58, no. 7 (2022): 1021–24. http://dx.doi.org/10.1039/d1cc06425h.

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A highly efficient, site-selective benzylic C–H bond amination of two different benzylic ether substrates was described by using bowl-shaped N-hydroxyimide organoradical catalysts with diethyl azodicarboxylate.
25

Matolcsy, György, Ágota Tombor, and Antal Gimesi. "Dithiocarbamate Derivatives as Herbicide Safeners." Zeitschrift für Naturforschung C 46, no. 9-10 (October 1, 1991): 815–18. http://dx.doi.org/10.1515/znc-1991-9-1016.

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Abstract The growing environmental and toxicological concern about the dichloroacetamide type herbicide safeners prompted us to search for alternative safener types. Based on analogy con­siderations, a random screening of structurally unrelated bivalent sulphur compounds was performed, followed by successive structure optimization phases representing both speculative and empirical elements. Dithiocarbamate ester type compounds derived from 1,4-exaza-spiro[4.5]decane revealed highest protecting potency both agains thiolcarbamate and chlor-acetanilide herbicides in corn (Zea mays L.), with the benzylic and allylic esters being the most active.
26

Xiao, Jing, Jia Yang, Tieqiao Chen, and Li-Biao Han. "Nickel-catalyzed synthesis of (E)-olefins from benzylic alcohol derivatives and arylacetonitriles via C–O activation." Chemical Communications 52, no. 10 (2016): 2157–60. http://dx.doi.org/10.1039/c5cc10005d.

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An efficient Ni-catalyzed synthesis of (E)-olefins using the readily available benzylic alcohol derivatives and arylacetonitriles is described. This transformation should proceed via a tandem process involving nickel-catalyzed cross coupling via C–O activation and subsequent stereoselective E2 elimination.
27

Benischke, Andreas D., Irina Knoll, Alice Rérat, Corinne Gosmini, and Paul Knochel. "A practical cobalt-catalyzed cross-coupling of benzylic zinc reagents with aryl and heteroaryl bromides or chlorides." Chemical Communications 52, no. 15 (2016): 3171–74. http://dx.doi.org/10.1039/c5cc10272c.

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A catalytic system consisting of 5 mol% CoCl2 and 10 mol% isoquinoline allows a convenient cross-coupling of benzylic zinc reagents with various aryl and heteroaryl bromides or chlorides leading to polyfunctionalized diaryl- and aryl-heteroaryl-methane derivatives.
28

Antonini, Cosimo, Franca M. Cordero, and Fabrizio Machetti. "5-(Benzoyloxymethyl)isoxazole-3-carboxylic Acid Ethyl Ester." Molbank 2024, no. 1 (January 16, 2024): M1762. http://dx.doi.org/10.3390/m1762.

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We describe here the palladium hydrogenation of ethyl 5-(benzoyloxymethyl)isoxazole-3-carboxylate. The presence of two reducible sites in the molecule, namely the benzylic-like position and the isoxazole N–O bond, creates a possible competition. The results show that under the applied conditions, ethyl (Z)-2-amino-4-oxo-2-pentanoate is obtained as the only product. Accordingly, a domino process occurs, consisting of deoxygenation to the 5-methylisoxazole derivative followed by reductive opening of the isoxazole ring. The isoxazole substrate was prepared by NaOH-catalyzed cycloaddition-condensation of ethyl nitroacetate and propargyl benzoate in water. Complete characterizations of the isoxazole and Z-enaminone derivatives are reported.
29

Liégault, Benoît, Jean-Luc Renaud, and Christian Bruneau. "Activation and functionalization of benzylic derivatives by palladium catalysts." Chem. Soc. Rev. 37, no. 2 (2008): 290–99. http://dx.doi.org/10.1039/b704255h.

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30

Egami, Hiromichi, Takafumi Ide, Yuji Kawato, and Yoshitaka Hamashima. "ChemInform Abstract: Benzylic C-H Trifluoromethylation of Phenol Derivatives." ChemInform 47, no. 12 (March 2016): no. http://dx.doi.org/10.1002/chin.201612054.

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31

Tajima, Toshiki, Hideki Ishii, and Toshio Fuchigami. "Anodic benzylic fluorination of toluene, ethylbenzene, and cumene derivatives." Electrochemistry Communications 4, no. 7 (July 2002): 589–92. http://dx.doi.org/10.1016/s1388-2481(02)00381-8.

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32

Reissig, Hans-Ulrich, and Fei Yu. "One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives." Beilstein Journal of Organic Chemistry 19 (September 18, 2023): 1399–407. http://dx.doi.org/10.3762/bjoc.19.101.

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The nucleophilic substitution of benzylic bromides with sodium azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl substituents. Hence, the precursor compounds 1,2-, 1,3- or 1,4-bis(bromomethyl)benzene furnished geometrically differing bis(1,2,3-triazole) derivatives. The use of tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) as ligand for the click step turned out to be very advantageous. The compounds with 1,2-oxazinyl end groups can potentially serve as precursors of divalent carbohydrate mimetics, but the reductive cleavage of the 1,2-oxazine rings to aminopyran moieties did not proceed cleanly with these compounds.
33

Cermenati, Laura, Maurizio Fagnoni, and Angelo Albini. "TiO2-photocatalyzed reactions of some benzylic donors." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 560–66. http://dx.doi.org/10.1139/v03-048.

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TiO2-photocatalyzed oxidation of toluene (1a), benzyltrimethylsilane (1b), and 4-methoxybenzyltrimethylsilane (1c) has been carried out in acetonitrile under oxygen, under nitrogen, and in the presence of electrophilic alkenes under various conditions (using Ag2SO4 as electron acceptor, adding 2.5% H2O, changing solvent to CH2Cl2). Benzyl radicals, formed via electron transfer and fragmentation, are trapped. A good material balance is often obtained. The overall efficiency of the process depends on the donor Eox, on the rate of fragmentation of the radical cation, and on the acceptor present (Ag+ is an efficient oxidant, an electrophilic alkene a poor one, O2 is intermediate). With ring-unsubstituted benzyl derivatives 1a and 1b, oxidative fragmentation occurs mainly close to the catalyst surface. The benzyl radicals form at a high local concentration and give benzaldehyde under O2, bibenzyl under N2 and dibenzylated derivatives by attack on the alkenes (acrylonitrile, fumaronitrile, maleic acid). In this case, using CH2Cl2–O2 enhances the yield of benzaldehyde. With methoxylated 1c, however, the radical cation migrates into the solution before fragmentation and, therefore, the free benzyl radical is formed. This radical in part is oxidized to the cation, giving a considerable amount of benzylacetamide (or of the alcohol with water), and in part is trapped by the alkenes. The last reaction is less efficient in this case and yields monobenzyl derivatives.Key words: photocatalysis, oxidation, alkylation.
34

Amaya, Toru, Hiroyuki Sakane, Takuto Nakata, and Toshikazu Hirao. "A theoretical study of the bowl-to-bowl inversion of sumanene derivatives." Pure and Applied Chemistry 82, no. 4 (March 19, 2010): 969–78. http://dx.doi.org/10.1351/pac-con-09-10-13.

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A theoretical study was conducted on the bowl-to-bowl inversion of sumanene: its benzylic mono-, di-, and trianion species and its mono-, di-, and trinaphthosumanenes. The use of B3LYP/6-311+G(2d,p) for the B3LYP/6-31G(d,p)-optimized geometries approximately reproduced the experimental values for the bowl-to-bowl inversion of sumanene, and its benzylic mono- and dianion species. The value for the trianion was estimated to be around 21 kcal/mol using the above levels. The investigation of naphthosumanenes clearly indicated a noted increase in the inversion barrier with additional fused rings. The calculated inversion barrier for mononaphthosumanene also correctly reproduced the experimental value (32.2 kcal/mol) using the above levels (31.4 kcal/mol). The calculated barrier for trinaphthosumanene reached 63.8 kcal/mol, therefore, the bowl-to-bowl inversion is less likely to occur under realistic conditions.
35

Rojas, Juan J., and James A. Bull. "4-Membered Ring Carbocations: A Positive Development in the Synthesis of 3,3-Disubstituted Oxetanes and Azetidines." CHIMIA 77, no. 4 (April 26, 2023): 192. http://dx.doi.org/10.2533/chimia.2023.192.

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4-Membered heterocycles are low molecular weight polar scaffolds with intriguing potential for drug discovery. Despite their unquestionable value, methods to access such heterocycles remain scant. Here, we describe the generation of oxetane- and azetidine- benzylic carbocations as a general strategy to access valuable 3,3-disubstituted derivatives.
36

Sato, Io, Yasuhiro Yamashita, and Shū Kobayashi. "Alkylpotassium-Catalyzed Benzylic C–H Alkylation of Alkylarenes with Alkenes." Synthesis 51, no. 01 (November 26, 2018): 240–50. http://dx.doi.org/10.1055/s-0037-1610378.

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Catalytic benzylic C–H alkylation reactions of alkylarenes with alkenes such as β-substituted styrenes and vinylsilanes have been achieved by utilizing alkylpotassium as a catalyst. Various substituted toluene derivatives can be alkylated under mild reaction conditions to afford the desired functionalized hydrocarbons in moderate to high yields.
37

Senthilkumar, B., R. G. Gonnade, and C. V. Ramana. "Pd-catalyzed benzylic C–H oxidation of cyclotriveratrylene – product diversity." Organic & Biomolecular Chemistry 13, no. 8 (2015): 2323–29. http://dx.doi.org/10.1039/c4ob02469a.

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38

Janke, Julia, Alexander Villinger, Peter Ehlers, and Peter Langer. "Synthesis of Acridones by Palladium-Catalyzed Buchwald–Hartwig Amination." Synlett 30, no. 07 (March 25, 2019): 817–20. http://dx.doi.org/10.1055/s-0037-1612256.

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The Buchwald–Hartwig amination allows an efficient and convenient synthesis of biologically and pharmaceutically important acridones by formation of a six-membered ring. With the described method, a number of derivatives have been synthesized in up to 95% yield by using a variety of anilines as well as benzylic and aliphatic amines.
39

K. Bandaru, Sravan, and Matthew C. Risi. "Zn(OAc)2.2H2O-Catalyzed C3-alkylation and O-alkylation of 4-Hydroxycoumarin derivatives." Caribbean Journal of Science and Technology 10, no. 02 (2022): 10–16. http://dx.doi.org/10.55434/cbi.2022.20102.

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or the C3-alkylation and O-alkylation of 4-hydroxycoumarins with benzylic, allylic, and corresponding acetates, respectively, under neat conditions at 60 0C with high product yield, Zn(OAc)2.2H2O has been found to be an effective reusable solid superacid catalyst.
40

Amaya, Toru, and Toshikazu Hirao. "Bowl-to-bowl inversion of sumanene derivatives." Pure and Applied Chemistry 84, no. 4 (February 15, 2012): 1089–100. http://dx.doi.org/10.1351/pac-con-11-09-09.

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Bowl-to-bowl inversion is one of the characteristic behaviors for some flexible open-end molecular bowls consisting of polycyclic aromatic hydrocarbons with benzene rings fused by imbedded five-membered rings (π bowls). This intriguing dynamics was studied with sumanene, which is the smallest C3v symmetric fragment of fullerenes. In this article, our ongoing research on the bowl-to-bowl inversion of sumanene, its benzylic anion species, hexasubstituted derivatives, mononaphthosumanene, and [CpRu(η6-sumenene)]+ complex is summarized. Estimation based on density functional theory (DFT) calculation is also described.
41

Dong, Yu, Jian Yang, Shuai He, Zhi-Chuan Shi, Yu Wang, Xiao-Mei Zhang, and Ji-Yu Wang. "Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)–H bonds." RSC Advances 9, no. 47 (2019): 27588–92. http://dx.doi.org/10.1039/c9ra05678e.

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A metal-free cross-dehydrogenative coupling of quinones with toluene derivatives has been established. A series of quinones were subjected to reaction with toluene derivatives in the presence of DTBP for direct synthesis of benzylquinones.
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Pohl, Martin, Wolf-Dieter Bloedorn, Clemens Mügge, and Jürgen Liebscher. "13C NMR Chemical Shift Assignments of Alkyl Chains of Histamine Analogous ω-Aminoalkylheterocycles and Bicyclic Derivatives." Collection of Czechoslovak Chemical Communications 59, no. 5 (1994): 1100–1104. http://dx.doi.org/10.1135/cccc19941100.

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ω-Aminoalkylheterocycles and aromatics as well as bicyclic azolodiazepine derivatives were investigated by means of CH-COSY and INADEQUATE experiments. The 13C NMR shifts of all carbon atoms of the aminopropyl and aminobutyl moieties could be assigned. The benzylic position of the ω-aminopropyl moieties appears most upfield rather than more downfield like erroneously reported in the literature.
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Tissaoui, Khalil, Noureddine Raouafi, and Khaled Boujlel. "Electrogenerated base-promoted synthesis ofN-benzylic rhodanine and carbamodithioate derivatives." Journal of Sulfur Chemistry 31, no. 1 (February 2010): 41–48. http://dx.doi.org/10.1080/17415990903191752.

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Sulpizio, Ada, Angelo Albini, Nicola D'Alessandro, Elisa Fasani, and Silvio Pietra. "Photochemical reaction between 1,4-naphthalenedicarbonitrile and .alpha.-substituted benzylic derivatives." Journal of the American Chemical Society 111, no. 15 (July 1989): 5773–77. http://dx.doi.org/10.1021/ja00197a041.

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45

Chen, Hongbiao, Litao Shen, and Yuanbin Lin. "ChemInform Abstract: Benzylic Bromination of Toluene Derivatives with Boron Tribromide." ChemInform 41, no. 40 (September 9, 2010): no. http://dx.doi.org/10.1002/chin.201040059.

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46

Drageset, Audun, Nils Åge Frøystein, Karl Wilhelm Törnroos, and Hans-René Bjørsvik. "A two-step telescoped continuous flow switchable process leading to nitriles, diaziridine or hydrazine derivatives." Reaction Chemistry & Engineering 4, no. 1 (2019): 41–51. http://dx.doi.org/10.1039/c8re00129d.

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Primary and benzylic alcohols were converted into nitriles on a continuous flow MJOD reactor platform or with a batch protocol. The two steps process involves TEMPO as the precatalyst with DIH and DCH as the terminal oxidants, respectively.
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Moeini, Seyed Sepehr, Simonetta Tuti, Chiara Battocchio, Igor Luisetto, and Daniela Tofani. "Solvent-Free Oxidation of Benzyl Alcohol Derivatives by In Situ Generated Redox Couple Pd(0)/PdOx Supported on Ceria Nanorods." Catalysts 13, no. 1 (December 21, 2022): 5. http://dx.doi.org/10.3390/catal13010005.

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Benzyl alcohol (BnOH) oxidation to benzaldehyde (PhCHO) is a pivotal industrial reaction. The aerobic oxidation of BnOH in solvent-free conditions is highly compatible with the necessity of low environmental impact. In this research work, palladium oxide (PdOx) supported on ceria nanorods (CeO2-NR), was synthesized, and utilized for aerobic solvent-free oxidation of BnOH derivatives to the corresponding aldehydes. The catalyst, PdOx/CeO2-NR, was characterized by X-ray diffraction (XRD), field-emission scanning electron microscopy/energy-dispersive spectroscopy (FE-SEM/EDS), N2 adsorption-desorption analysis, temperature-programmed reduction with hydrogen (H2-TPR), and X-ray Photoelectron Spectroscopy (XPS), proving that the PdOx (x > 1) particles were highly dispersed on CeO2-NR and have a strong interaction with the support. The PdOx/CeO2-NR catalyst permitted the aerobic oxidation of various benzyl alcohol derivatives with good conversion, and high selectivity towards the corresponding aldehydes. The presence of electron donating groups (EDG) on the benzylic ring enhanced the reactivity as opposed to the electron withdrawing groups (EWG) which were detrimental for the catalytic activity. During the reaction a partial reduction of the metal produced a Pd(0)/PdOx/CeO2-NR redox couple stable in the reaction condition, more reactive and recyclable. Some mechanistic hypotheses are presented.
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Jeremic, Marko, Jelena Dinic, Milica Pesic, Marija Stepanovic, Irena Novakovic, Dejan Segan, and Dusan Sladic. "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential." Journal of the Serbian Chemical Society 83, no. 11 (2018): 1193–207. http://dx.doi.org/10.2298/jsc180627062j.

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In this paper, the synthesis of fourteen alkylamino and arylamino derivatives of sesquiterpene quinone avarone and its model compound tert-butylquinone is described. Branched, cyclic, allylic and benzylic alkylamino/arylamino groups were introduced into the quinone moiety. For all the obtained derivatives, their biological activity and redox properties were studied. The cytotoxic activity of the synthesized derivatives towards multidrug resistant (MDR) human non-small cell lung carcinoma NCI-H460/R cells, their sensitive counterpart NCI-H460 and human normal keratinocytes (HaCaT) was investigated. The antimicrobial activity towards Gram-positive and Gram-negative bacteria, and fungal cultures was determined. Some of the synthesized derivatives showed selectivity for cancer cells, including MDR cells. Regarding their cell death induction potential, the most promising compounds were allylamino derivatives, preferentially triggering apoptosis, with high selectivity for cancer cells, including MDR cells. Several compounds showed promising antimicrobial activity, comparable to those of commercial antibiotic and antimycotic agents.
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Chatwichien, Jaruwan, Buntarika Prachavna, Rinrada Suntivich, and Sarawut Kumphune. "NSCLC Structure-activity Relationship (SAR) Study of Diisothiocyanates for Antiproliferative Activity on A549 Human Non-small Cell Lung Carcinoma (NSCLC)." Letters in Organic Chemistry 16, no. 7 (May 30, 2019): 569–74. http://dx.doi.org/10.2174/1570178615666181011145219.

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Isothiocyanate functional group (-N=C=S) is widely accepted as an important moiety for anti- cancer effects of naturally occurring isothiocyanate compounds (ITCs). Herein, a series of diisothiocyanate (diITCs) derivatives were synthesized and evaluated in antiproliferative assays on A549 human non-small cell lung cancer and IMR90 human foetal lung cell lines for structure-activity relationship (SAR) and cancer cell selectivity studies. Results showed that aliphatic and benzylic diITCs were more cytotoxic to A549 cells than natural ITCs; benzyl isothiocyanate (BITC) and phenyl isothiocyanate (PITC), and a currently available anticancer drug; etoposide. Aromatic diITCs were not as active. Notably, most of the diITCs reported in this work were significantly more selective than etoposide to inhibit proliferation of the cancer cells (A549) over the normal cells (IMR90). This study demonstrated a guideline to modify chemical structures of diITCs for anti-NSCLC agents.
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Holland, Herbert L., Eleanor J. Bergen, P. Chinna Chenchaiah, Shaheer H. Khan, Benito Munoz, Ronald W. Ninniss, and Denise Richards. "Side chain hydroxylation of aromatic compounds by fungi.: 1. Products and stereochemistry." Canadian Journal of Chemistry 65, no. 3 (March 1, 1987): 502–7. http://dx.doi.org/10.1139/v87-087.

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The fungus Mortierellaisabellina can convert ethylbenzene and a number of para-substituted derivatives to the corresponding optically active 1-phenylethanols with enantiomeric excesses between 5 and 40% and chemical yields up to 45%. 2-Ethylnaphthalene, 2-ethylthiophene, and n-propylbenzene were similarly converted, as were the bicyclic compounds indane and tetralin. In most cases, the R absolute configuration of product predominated. The fungi Cunninghamellaechinulata var. elegans and Helminthosporium species are also capable of performing some of these transformations. M. isabellina and C. elegans also produce 2-phenylethanols as products in some cases. The highest enantiomeric excesses during benzylic hydroxylation were obtained with Helminthosporium and are attributable, at least in part, to further stereoselective oxidation of the alcohol. Cross induction experiments with M. isabellina indicate that the same enzyme may be responsible for the benzylic hydroxylation of ethylbenzene, 2-ethylthiophene, and 2-ethylnaphthalene.
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