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Journal articles on the topic 'Benzoyl Migration'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Delogu, Giovanna Lucia, and Michela Begala. "Unexpected Migration of Benzoyl Group in the Synthesis of 3-Benzoyl-2-Phenylbenzofurans under Wittig Conditions." Proceedings 9, no. 1 (2018): 38. http://dx.doi.org/10.3390/ecsoc-22-05656.

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In the present work, we report the unexpected formation of isomeric 3-benzoyl-2-phenylbenzo[b]furans using triphenylphosphonium salt and benzoyl chlorides under Wittig conditions. In particular, we found that the o-[(benzoyloxy)benzyl]-triphenyl-phosphoranes constitute the key intermediate that reasonably undergoes benzoyl group migration.

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2

Kononov, Leonid O., Elena V. Stepanova, Alexander I. Zinin, Polina I. Abronina, and Alexander O. Chizhov. "Azidation of Partially Protected Carbohydrate Derivatives: Efficient Suppression of Acyl Migration." Synlett 31, no. 15 (2020): 1491–96. http://dx.doi.org/10.1055/s-0040-1707137.

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Although azidation by nucleophilic substitution is widely used in organic chemistry, it has a limitation for partially protected carbohydrate derivatives under typical reaction conditions used for azidation (heating with NaN3, phase-transfer catalyst (optional), DMF or DMSO) as it can cause substantial migration (70%) of O-acyl protective groups. Several approaches, including the use of a temporary protective group for the unprotected hydroxyl group, to avoid acyl migration have been compared. Addition of excess of ethyl trifluroacetate effectively suppressed benzoyl migration but inhibited su

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3

Tamboli, Majid I., Vir Bahadur, Rajesh G. Gonnade, and Mysore S. Shashidhar. "Correlation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4′-bipyridine cocrystal with their crystal structures." Acta Crystallographica Section C Structural Chemistry 70, no. 11 (2014): 1040–45. http://dx.doi.org/10.1107/s2053229614021834.

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Racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate, C21H18O8,(1), shows a very efficient intermolecular benzoyl-group migration reaction in its crystals. However, the presence of 4,4′-bipyridine molecules in its cocrystal, C21H18O8·C10H8N2,(1)·BP, inhibits the intermolecular benzoyl-group transfer reaction. In(1), molecules are assembled around the crystallographic twofold screw axis (baxis) to form a helical self-assembly through conventional O—H...O hydrogen-bonding interactions. This helical association places the reactive C6-O-benzoyl group (electrophile, El) and the C4-hydroxy gr

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4

Chaudhary, Ashok G., Mahendra D. Chordia, and David G. I. Kingston. "A Novel Benzoyl Group Migration: Synthesis and Biological Evaluation of 1-Benzoyl-2-des(benzoyloxy)paclitaxel." Journal of Organic Chemistry 60, no. 10 (1995): 3260–62. http://dx.doi.org/10.1021/jo00115a050.

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5

Scheffer, John R., and Kodumuru Vishnumurthy. "The photochemistry of trans-1,4,4,4-tetraphenyl-but-2-en-1-one: A highly efficient aryl migration (type B) enone photorearrangement." Canadian Journal of Chemistry 81, no. 6 (2003): 705–8. http://dx.doi.org/10.1139/v03-030.

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Photolysis of trans-1,4,4,4-tetraphenylbut-2-en-1-one (3) in acetonitrile or benzene leads to transcis isomerization (7) along with rearrangement to trans-1-benzoyl-2,2,3-triphenylcyclopropane (8). Formation of the latter product represents a new example of the aryl migration (type B) enone photorearrangement reaction first reported by Zimmerman and co-workers for 4,4-diphenylcyclohex-2-en-1-one (1). The quantum yield in the case of enone 3 (0.4) is approximately 10 times greater than that for 4,4,-diphenylcyclohex-2-en-1-one, a result that is ascribed to steric acceleration of phenyl migrati

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6

Warkentin, John, та John Mck R. Woollard. "Photolysis of 5,5-dibenzyl-Δ3-1,3,4-oxadiazolines". Canadian Journal of Chemistry 75, № 3 (1997): 289–307. http://dx.doi.org/10.1139/v97-033.

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Photolysis of dibenzyl-Δ3-1,3,4-oxadiazolines (3) in the presence of dimethyl acetylenedicarboxylate (DMAD) gives only modest yields of the expected symmetrical 3,3-dibenzylcyclopropenes (4), but these are accompanied by more than six by-products, including unsymmetrical cyclopropenes, methylenecyclopropanes, and various pyrazoles. The origin of this array of products can be explained by a series of steps starting with photolysis of 3 to form a diazoalkane that undergoes 1,3-dipolar cycloaddition to DMAD, generating a 3H-pyrazole as initial product. The latter is further photolyzed to a symmet

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7

Begala, Michela, Michele Mancinelli, and Giovanna Lucia Delogu. "Unexpected migration of a benzoyl group in the intramolecular Wittig reaction of o-acyloxybenzylidenephosphoranes with benzoyl chlorides: One-pot synthesis of isomeric 3-benzoyl-2-phenylbenzofurans." Tetrahedron Letters 61, no. 12 (2020): 151634. http://dx.doi.org/10.1016/j.tetlet.2020.151634.

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8

Lin, Lee-Gin, Pi-Guey Su, Jun-Ren Huang, et al. "25-Alkoxy-26-benzoyloxycalix[4]arenes: the reaction mechanism of benzoyl migration." Tetrahedron Letters 53, no. 27 (2012): 3510–13. http://dx.doi.org/10.1016/j.tetlet.2012.04.138.

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9

Mendoza-Morales, William O., Esteban Rodríguez, Aliana González, et al. "Synthesis, Structure, Electrochemistry, and In Vitro Anticancer and Anti-Migratory Activities of (Z)- and (E)-2-Substituted-3-Ferrocene-Acrylonitrile Hybrids and Their Derivatives." Molecules 30, no. 13 (2025): 2835. https://doi.org/10.3390/molecules30132835.

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In this study, a series of (Z)- and (E)-2-substituted-3-ferrocene-acrylonitrile derivatives were synthesized, characterized, and evaluated in vitro for their anticancer and anti-migration properties. The compounds were synthesized via the Knoevenagel condensation of the appropriate benzyl cyanide or benzoyl acetonitrile with ferrocenecarboxaldehyde 1, producing isolated yields of 99 to 23%. The structures of the compounds were analyzed using IR, 1H NMR, 13C{1H} NMR, GC-MS, and UV/Vis spectroscopic methods. Single-crystal X-ray diffraction analysis of representative compounds 21, 27, and 29 dem

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10

Rijsbergen, Ronan Van, Marc Anteunis та André De Bruyn. "Trans Benzoyl Migration in 1.6-Anhydro-2-azido-4-O-benzoyl-2-deoxy-β-D-glucopyranose in Non-Aqueous Basic Medium". Journal of Carbohydrate Chemistry 5, № 2 (1986): 329–33. http://dx.doi.org/10.1080/07328308608062970.

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11

Bérces, Attila, Dennis M. Whitfield, Tomoo Nukada, Iwona do Santos Z., Agnes Obuchowska, and Jiri J. Krepinsky. "Is acyl migration to the aglycon avoidable in 2-acyl assisted glycosylation reactions?" Canadian Journal of Chemistry 82, no. 7 (2004): 1157–71. http://dx.doi.org/10.1139/v04-059.

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This report unequivocally separates orthoester formation from acyl transfer for the first time and indicates possible routes to eliminate 2-O-acyl transfer during glycosylation reactions. Experimental evidence is shown that acyl transfer from 2-O-acyl-3,4,6-tri-O-benzyl-D-galactopyranose-derived glycosyl donors decreases in the order formyl > acetyl > pivaloyl. The 2-O-benzoyl derivatives are more variable, in some cases transferring easily, and in others not at all. Density functional theory (DFT) calculations of the structure and energetics of dioxolenium ion and related intermediates

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12

Brown, RFC, FW Eastwood, GD Fallon, SC Lee, and RP Mcgeary. "The Pyrolytic Rearrangement of 1-Alkynoyl-3-methylpyrazoles: Synthesis of Pyrazolo[1,5-a]pyridin-5-ols and Related Compounds." Australian Journal of Chemistry 47, no. 6 (1994): 991. http://dx.doi.org/10.1071/ch9940991.

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Flash vacuum pyrolysis of 1-(alkyn-2′-oyl)-3-methylpyrazoles at 650°/0.03 mm forms pyrazolo[1,5-a]pyridin-5-ols, often in high yield, which may bear substituents at C2, C3 or C7. In the absence of a 3-methyl group in the precursor, N-ethynylpyrazoles are formed in low yield. The formation of both types of product is interpreted as involving 3-(N-pyrazolyl)propadienones formed by N1 → N2 migration of the N-alkynoyl group with inversion of the three-carbon chain. The fused-ring structure of 2-methylpyrazolo[1,5-a]pyridin-5-ol (25) was established by X-ray crystallography of the O-benzoyl derivat

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13

Idzko, Marco, Stefan Dichmann, Davide Ferrari, et al. "Nucleotides induce chemotaxis and actin polymerization in immature but not mature human dendritic cells via activation of pertussis toxin–sensitive P2y receptors." Blood 100, no. 3 (2002): 925–32. http://dx.doi.org/10.1182/blood.v100.3.925.

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Abstract Dendritic cells (DCs) are considered the principal initiators of immune response because of their ability to migrate into peripheral tissues and lymphoid organs, process antigens, and activate naive T cells. There is evidence that extracellular nucleotides regulate certain functions of DCs via G-protein–coupled P2Y receptors (P2YR) and ion-channel–gated P2X receptors (P2XR). Here we investigated the chemotactic activity and analyzed the migration-associated intracellular signaling events such as actin reorganization and Ca++ transients induced by common P2R agonists such as adenosine

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14

Kesuma, Dini, Galih S. Putra, Tegar A. Yuniarta, et al. "Synthesis and in vitro activity tests of N-benzoyl-N'-phenylthiourea derivatives as macrophage migration inhibitory factor." Journal of Pharmacy & Pharmacognosy Research 11, no. 5 (2023): 902–25. http://dx.doi.org/10.56499/jppres23.1657_11.5.902.

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Context: The COVID-19 pandemic in 2020 resulted in widespread mortalities due to cytokine storms in the affected patients. Macrophage migration inhibitory factor (MIF) is one of the most interesting targets in developing anti-COVID-19 drugs. Some thiourea compounds have been identified as having potential as MIF inhibitors. Aims: To investigate MIF inhibitory activity of N-benzoyl-N'-phenylthiourea derivatives. Methods: The study consists of in-silico activity prediction of designed compounds using a molecular docking approach against MIF protein (PDB ID: 1LJT). Afterwards, the designed compou

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15

Pyo, Sang-Hyun, Jin-Suk Cho, Ho-Joon Choi, and Byung-Hee Han. "Evaluation of paclitaxel rearrangement involving opening of the oxetane ring and migration of acetyl and benzoyl groups." Journal of Pharmaceutical and Biomedical Analysis 43, no. 3 (2007): 1141–45. http://dx.doi.org/10.1016/j.jpba.2006.08.026.

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16

Hu, Zhiyong, and Paul W. Erhardt. "Utilization of a Benzoyl Migration To Effect an Expeditious Synthesis of the Paclitaxel C-13 Side Chain." Organic Process Research & Development 1, no. 5 (1997): 387–90. http://dx.doi.org/10.1021/op970113b.

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17

Rossetti, Monica, Pierluigi Stipa, Rita Petrucci, and Lucedio Greci. "Reactions between 1-Methyl-2-Phenyl-3-Nitrosoindole, Activated with Benzoyl Chloride, with Indole and Indolizine Derivatives as Nucleophiles: A Case of 1,3-Migration." Journal of Chemical Research 23, no. 6 (1999): 362–63. http://dx.doi.org/10.1177/174751989902300609.

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18

Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Carba Analogues of Deoxy-4-C-(hydroxymethyl)pentofuranoses, Intermediates in the Synthesis of Carbocyclic Nucleosides." Collection of Czechoslovak Chemical Communications 63, no. 12 (1998): 2044–64. http://dx.doi.org/10.1135/cccc19982044.

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Racemic dimethyl 4-methoxy- (11 and 12), diallyl 4-allyloxy- (13 and 14) and dimethyl 4-(ethylsulfanyl)-2-hydroxycyclopentane-1,1-dicarboxylates (15 and 16) were prepared by base-catalyzed addition of methanol, allyl alcohol and ethylsulfane, respectively, to dimethyl (4-oxobut-2-en-1-yl)malonate (6). Deallylation of 13 and 14 afforded 4-hydroxycyclopentanes 27 and 28. Reduction of 11-16 with lithium aluminium hydride gave the corresponding 4-substituted 2,2-bis(hydroxymethyl)cyclopentanols. Dimethyl (2S,3S,4R)-, (2R,3S,4R)-3-benzyloxy-4-formyloxy-2-hydroxycyclopentane-1,1-dicarboxylates (35,

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19

Aumo, Linda, Marte Rusten, Gunnar Mellgren, Marit Bakke, and Aurélia E. Lewis. "Functional Roles of Protein Kinase A (PKA) and Exchange Protein Directly Activated by 3′,5′-Cyclic Adenosine 5′-Monophosphate (cAMP) 2 (EPAC2) in cAMP-Mediated Actions in Adrenocortical Cells." Endocrinology 151, no. 5 (2010): 2151–61. http://dx.doi.org/10.1210/en.2009-1139.

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In the adrenal cortex, the biosynthesis of steroid hormones is controlled by the pituitary-derived hormone ACTH. The functions of ACTH are principally relayed by activating cAMP-dependent signaling pathways leading to the induction of genes encoding enzymes involved in the conversion of cholesterol to steroid hormones. Previously, protein kinase A (PKA) was thought to be the only direct effector of cAMP. However, the discovery of the cAMP sensors, exchange proteins directly activated by cAMP (EPAC1 and 2), has led to a reevaluation of this assumption. In the present study, we demonstrate the o

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20

Gao, Zhipei, Yongli Du, Xiehuang Sheng та Jingkang Shen. "Molecular Dynamics Simulations Based on 1-Phenyl-4-Benzoyl-1-Hydro-Triazole ERRα Inverse Agonists". International Journal of Molecular Sciences 22, № 7 (2021): 3724. http://dx.doi.org/10.3390/ijms22073724.

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Estrogen-related receptor α (ERRα), which is overexpressed in a variety of cancers has been considered as an effective target for anticancer therapy. ERRα inverse agonists have been proven to effectively inhibit the migration and invasion of cancer cells. As few crystalline complexes have been reported, molecular dynamics (MD) simulations were carried out in this study to deepen the understanding of the interaction mechanism between inverse agonists and ERRα. The binding free energy was analyzed by the MM-GBSA method. The results show that the total binding free energy was positively correlate

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21

HU, Z., and P. W. ERHARDT. "ChemInform Abstract: Utilization of a Benzoyl Migration to Effect an Expeditious Synthesis of the Paclitaxel C-13 Side Chain." ChemInform 29, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199807124.

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22

MITTERAUER, Thomas, Christian NANOFF, Horst AHORN, Michael FREISSMUTH, and Martin HOHENEGGER. "Metal-dependent nucleotide binding to the Escherichia coli rotamase SlyD." Biochemical Journal 342, no. 1 (1999): 33–39. http://dx.doi.org/10.1042/bj3420033.

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Upon expression and purification of the first catalytic domain of mammalian adenylate cyclase type 1 (IC1), a 27 kDa contaminant was observed, which was labelled by three radioactive ATP analogues (8-azido-ATP, 3′-O-(4-benzoyl)benzoyl-ATP and 2′,3′-dialdehyde-ATP); the protein was purified separately and identified as Escherichiacoli SlyD by N-terminal amino acid sequence determination. SlyD is the host protein required for lysis of E.coli upon infection with bacteriophage ΦX174 and has recently been shown to display rotamase (peptidylproline cis-trans-isomerase) activity. The covalent incorpo

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23

Wang, Zhi-zhong, Meng-ying Liu, Run-hua Lu, Xue-yan Fu та Gui-dong Dai. "Direct regioselective benzoylation of a single C-2 hydroxyl group of β-cyclodextrin and its hydrolysis via benzoyl group migration". Monatshefte für Chemie - Chemical Monthly 142, № 12 (2011): 1283–87. http://dx.doi.org/10.1007/s00706-011-0566-7.

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24

Sagha, Mohsen, Kia Afghah Mortazavi, Jafar Abbasi Shiran, Azadeh Aghvami Tehrani, and Nima Razzaghi-Asl. "New 1-Arylmethyl-3-Benzoyl/Cyclopropanoyl Thioureas as inhibitors of AGS cell line migration: Synthesis, biological evaluation and molecular dynamics." Journal of Molecular Structure 1312 (September 2024): 138621. http://dx.doi.org/10.1016/j.molstruc.2024.138621.

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25

van den Heede, Philip, Bjorn van Belleghem, Maria Adelaide Araújo, João Feiteira, and Nele de Belie. "Screening of Different Encapsulated Polymer-Based Healing Agents for Chloride Exposed Self-Healing Concrete Using Chloride Migration Tests." Key Engineering Materials 761 (January 2018): 152–58. http://dx.doi.org/10.4028/www.scientific.net/kem.761.152.

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The service life of steel reinforced concrete in aggressive marine environments could be increased substantially by embedding a self-healing mechanism that ensures autonomous healing of cracks upon their occurrence. Previous proof-of-concept experiments have shown that the incorporation of encapsulated polymer-based healing agents (HAs) counts as a very appropriate way to achieve this goal. Over the years, several polymer-precursor-capsule systems have been developed in that perspective at our laboratory. Cementitious materials containing either commercial or in-house developed encapsulated HA

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26

Li, Lanlan, Mingfei Yang, Jia Yu, et al. "A Novel L-Phenylalanine Dipeptide Inhibits the Growth and Metastasis of Prostate Cancer Cells via Targeting DUSP1 and TNFSF9." International Journal of Molecular Sciences 23, no. 18 (2022): 10916. http://dx.doi.org/10.3390/ijms231810916.

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Prostate cancer (PCa) is a common malignant cancer of the urinary system. Drug therapy, chemotherapy, and radical prostatectomy are the primary treatment methods, but drug resistance and postoperative recurrence often occur. Therefore, seeking novel anti-tumor compounds with high efficiency and low toxicity from natural products can produce a new tumor treatment method. Matijin-Su [N-(N-benzoyl-L-phenylalanyl)-O-acetyl-L-phenylalanol, MTS] is a phenylalanine dipeptide monomer compound that is isolated from the Chinese ethnic medicine Matijin (Dichondra repens Forst.). Its derivatives exhibit v

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27

Biggs, Tim N., and John S. Swenton. "Model studies on the reactions of N-acetyl-2-aminofluorene metabolites. An intramolecular oxygen migration from an N-benzoyl quinol imine intermediate." Journal of the American Chemical Society 115, no. 22 (1993): 10416–17. http://dx.doi.org/10.1021/ja00075a090.

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28

Iwamura, Tatsunori, Takashi Ichikawa, Hiroshi Shimizu, et al. "Novel benzoyl migration of the intermediary 1:1 adducts of 1,3-dipolar cycloaddition of thiazolo[3,2-b][1,2,4]-triazolium N-phenacylides with dimethyl acetylenedicarboxylate." Tetrahedron Letters 35, no. 26 (1994): 4587–90. http://dx.doi.org/10.1016/s0040-4039(00)60737-2.

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29

Rossetti, Monica, Pierluigi Stipa, Rita Petrucci, and Lucedio Greci. "Reactions between 1-Methyl-2-phenyl-3-nitrosoindole, Activated with Benzoyl Chloride, with Indole and Indolizine Derivatives as Nucleophiles: a Case of 1,3-Migration." Journal of Chemical Research, no. 6 (1999): 362–63. http://dx.doi.org/10.1039/a900849g.

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30

Zhang, Xiang. "Mechanistic insights into the Ag(I)-catalyzed aryl migration." Canadian Journal of Chemistry 95, no. 5 (2017): 620–26. http://dx.doi.org/10.1139/cjc-2016-0574.

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Theoretical investigation has been conducted into the mechanism for the Ag(I)/PhI(OTFA)2-catalyzed 1,4-radical aryl migration from carbon center to nitrogen center in sulfonamides by using density functional theory (DFT). The calculations show that 11 elementary reactions compose the whole catalytic reaction, which includes the deprotonation, the oxidation of Ag(I) intermediate to Ag(II) intermediate, the formation of nitrogen radical, the 1,4-radical aryl migration, the oxidation of benzyl radical to benzyl cation, etc. The difference between sulfonamides and other amides in the deprotonation

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31

Titov, Oleksii, and Viktor Brygadyrenko. "Influence of Synthetic Flavorings on the Migration Activity of Tribolium confusum and Sitophilus granarius." Ekológia (Bratislava) 40, no. 2 (2021): 163–77. http://dx.doi.org/10.2478/eko-2021-0019.

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Abstract Flavorings and volatile biologically active substances, used by humans for various purposes, may potentially have fumigating, repellent, or attractive effects on various species of anthropod storage pests. Tribolium confusum Jacquelin du Val, 1863 (Tenebrionidae) and Sitophilus granarius (Linnaeus, 1758) (Curculionidae) are the two most abundant pests of grain and grain products; the damage they cause to stored products of horticulture is 5–20% of the total yield of grain crops. In the experiment, we video-recorded migratory activity of beetles and evaluated it according to standard t

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32

IWAMURA, T., T. ICHIKAWA, H. SHIMIZU, et al. "ChemInform Abstract: Novel Benzoyl Migration of the Intermediary 1:1 Adducts of 1,3-Dipolar Cycloaddition of Thiazolo(3,2-b) (1,2,4)triazolium N-Phenacylides with Dimethyl Acetylenedicarboxylate." ChemInform 25, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199447152.

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33

Rossetti, Monica, Pierluigi Stipa, Rita Petrucci, and Lucedio Greci. "ChemInform Abstract: Reactions Between 1-Methyl-2-phenyl-3-nitrosoindole, Activated with Benzoyl Chloride, with Indole and Indolizine Derivatives as Nucleophiles: A Case of 1,3-Migration." ChemInform 30, no. 42 (2010): no. http://dx.doi.org/10.1002/chin.199942126.

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34

Hasegawa, Akira, Makoto Goto та Makoto Kiso. "An Unusual Behavior of Methyl or Benzyl 3-Azido-5-O-Benzoyl-3,6-Di-Deoxy-α-L-Talofuranoside with (Dimethylamino)Sulfur Trifluoride; Migration of the Alkoxyl Group from the C-1 to the C-2 Position". Journal of Carbohydrate Chemistry 4, № 4 (1985): 627–38. http://dx.doi.org/10.1080/07328308508082680.

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35

Iwamura, Tatsunori, Takashi Ichikawa, Hiroshi Shimizu, and Tadashi Kataoka. "Reactions of Thiazolo[3,2-6]-1,2,4-triazolium N-Ylides with Electron-deficient Acetylenes: Novel Benzoyl Migration of Intermediary 1:l-Adducts and Michael Addition to the Acetylenes." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (1997): 471–72. http://dx.doi.org/10.1080/10426509708044034.

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36

Iwamura, Tatsunori, Takashi Ichikawa, Hiroshi Shimizu, and Tadashi Kataoka. "Reactions of Thiazolo[3,2-b]-1,2,4-triazolium N-Ylides with Electron-deficient Acetylenes: Novel Benzoyl Migration of Intermediary 1:1-Adducts and Michael Addition to the Acetylenes." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (1997): 471–72. http://dx.doi.org/10.1080/10426509708545602.

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37

McGall, Glenn H., JoAnne Stubbe, and John W. Kozarich. "Acyl migration in the production of thymine. Propenal from 3'-O-benzoyl-5'-deoxy-4'-(hydroperoxy)thymidine: a reinterpretation of a putative model for bleomycin-mediated DNA degradation." Journal of Organic Chemistry 56, no. 1 (1991): 48–55. http://dx.doi.org/10.1021/jo00001a011.

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38

Argunov, Dmitry A., Vadim B. Krylov, and Nikolay E. Nifantiev. "The Use of Pyranoside-into-Furanoside Rearrangement and Controlled O(5) → O(6) Benzoyl Migration as the Basis of a Synthetic Strategy To Assemble (1→5)- and (1→6)-Linked Galactofuranosyl Chains." Organic Letters 18, no. 21 (2016): 5504–7. http://dx.doi.org/10.1021/acs.orglett.6b02735.

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39

Hudrlik, Paul F., Jose O. Arango, Yousef M. Hijji, Cosmas O. Okoro, and Anne M. Hudrlik. "Alkoxides of o-silyl benzyl alcohols in cleavage reactions: approaches to benzyl and silyl anion equivalents." Canadian Journal of Chemistry 78, no. 11 (2000): 1421–27. http://dx.doi.org/10.1139/v99-250.

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The alkoxides of o-silyl benzyl alcohols 4 undergo cleavage reactions under mild conditions allowing transfer of a benzyl or silyl group to an electrophile. Reactions 3a [Formula: see text] 8, and 3c or 4c [Formula: see text] 11 illustrate their potential as benzyl and silyl anion equivalents.Key words: silyl migration, benzyl anion equivalent, silyl anion equivalent, β-silyl ketone, γ-hydroxysilane.

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40

Mori, Akira, Nobuo Kato, Hitoshi Takeshita, et al. "Roles of sigmatropic migration of a benzoyl group and intermolecular hydrogen bonding between a tropone carbonyl and an NH group on the mesomorphic properties of 2-(4-alkoxybenzoyloxy)-5-alkylaminotropones and 5-alkoxy-2-(4-alkylaminobenzoyloxy)tropo." Liquid Crystals 28, no. 9 (2001): 1425–33. http://dx.doi.org/10.1080/02678290110067245.

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41

Ledvina, Miroslav, Daniel Zyka, Jan Ježek, Tomáš Trnka та David Šaman. "New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity". Collection of Czechoslovak Chemical Communications 63, № 4 (1998): 577–89. http://dx.doi.org/10.1135/cccc19980577.

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Ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (5), prepared by benzylation of ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4), was transformed by reaction with bromine into 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (6). Thioglycoside 5 in the presence of methyl triflate and glycosylbromide 6 in the presence of silver triflate were used as glycosyl donors for condensation with benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (7), to give benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-p

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42

Tokmakov, G. P., and I. I. Grandberg. "1,2-Migration of the benzyl group in indoles." Chemistry of Heterocyclic Compounds 30, no. 1 (1994): 121. http://dx.doi.org/10.1007/bf01164747.

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Prema, Dipesh, Yohan L. N. Mathota Arachchige, Rex E. Murray, and LeGrande M. Slaughter. "“Decarbonization” of an imino-N-heterocyclic carbene ligand via triple benzyl migration from hafnium." Chemical Communications 51, no. 31 (2015): 6753–56. http://dx.doi.org/10.1039/c5cc01560j.

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Hartshorn, MP, JM Readman, WT Robinson, CW Sies, and GJ Wright. "The Nitration of 3,4,5,6-Tetramethylbenzene-1,2-Dicarbonitrile, 2,3,5,6-Tetramethylbenzonitrile, 1,2,3-Trimethyl-4,6-Dinitrobenzene and 1,2,4,5-Tetramethyl-3,6-Dinitrobenzene. Methyl Migrations Following ipso-Substitution." Australian Journal of Chemistry 41, no. 3 (1988): 373. http://dx.doi.org/10.1071/ch9880373.

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Nitration of 3,4,5,6-tetramethylbenzene-1,2-dicarbonitrile (1a) gives epimeric pairs of dinitro ketones (6a) and (7a), and hydroxy ketones (9) and (10), in addition to the benzyl nitrate (4) and phthalide (5). Nitration of 2,3,5,6-tetramethylbenzonitrile (11) gives the epimeric dinitro ketones (15) and (16), in addition to the nitrobenzonitrile (12) and the nitrophthalide (13). Nitration of 1,2,3-trimethyl-4,6- dinitrobenzene (17) gives dimethylpropanedioic acid (23), the dinitrobenzoic acid (24), and the hydroxy dienone (25). Nitration of 1,2,4,5-tetramethyl-3,6-dinitrobenzene (18) gives dime

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45

Boontawee, Hasleena, Charoen Nakason, Azizon Kaesaman, Anoma Thitithammawong, and Sopa Chewchanwuttiwong. "Comparative Properties of Vegetable Oil-Based Benzyl Esters and Vegetable Oils as Processing Oil in Natural Rubber Compounds." Advanced Materials Research 626 (December 2012): 237–39. http://dx.doi.org/10.4028/www.scientific.net/amr.626.237.

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The vegetable oil tends to be incompatible and insoluble in the rubber hydrocarbon. They can migrate to the surface of the uncured rubber. To overcome this problem, fatty acid esters that are soluble in rubber material and minimize migration were prepared. Benzyl esters of three different types of vegetable oils (i.e., coconut, palm, and soybean oils) were prepared by reacting fatty acids of vegetable oil with benzyl alcohol. They were then used as processing oil in rubber compounding and processing compared with the one with unmodified vegetable oils. It was found that the benzyl esters of th

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46

Samsoniya, Sh A., I. Sh Chikvaidze, and �. O. Gogrichiani. "Unexpected migration of the benzyl group in N-benzylindoles." Chemistry of Heterocyclic Compounds 30, no. 8 (1994): 993–94. http://dx.doi.org/10.1007/bf01165044.

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47

Street, Ian P., and Stephen G. Withers. "Fluorination of protected mannose derivatives using diethylaminosulfur trifluoride." Canadian Journal of Chemistry 64, no. 7 (1986): 1350–53. http://dx.doi.org/10.1139/v86-231.

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3,4,6-Tri-O-benzyl-D-mannose and methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside were subjected to fluorination by diethylaminosulfur trifluoride and each produced two products. The former suffered fluorination at the anomeric centre to give the α-fluoride and, to a lesser extent, additionally at C-2 to give the 2-fluoro-2-deoxy-β-D-glucopyranosyl fluoride. The methyl mannoside underwent a methyl ether migration reaction to produce a 1:1 mixture of the α- and β-2-O-methyl glucosyl fluorides. A mechanism for this rearrangement is proposed and 1H and 19F nmr data are presented for all products.

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Hossian, Asik, and Ranjan Jana. "Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement." Organic & Biomolecular Chemistry 14, no. 41 (2016): 9768–79. http://dx.doi.org/10.1039/c6ob01758d.

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A silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen is reported.

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Veselý, Jan, Miroslav Ledvina, Jindřich Jindřich, Tomáš Trnka та David Šaman. "Synthesis of 2-Amino-2-deoxy-β-D-galactopyranosyl-(1→4)-2-amino-2-deoxy-β-D-galactopyranosides: Using Various 2-Deoxy-2-phthalimido-D-galactopyranosyl Donors and Acceptors". Collection of Czechoslovak Chemical Communications 69, № 10 (2004): 1914–38. http://dx.doi.org/10.1135/cccc20041914.

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A systematic study is presented of the efficiency of the most common glycosylation methods using standard 2-deoxy-2-phthalimidogalactopyranosyl donors ethyl 4-O-acetyl-3,6-di-O- benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (3a), 4-O-Acetyl-3,6-di-O-benzyl- 2-deoxy-2-phthalimido-β-D-galactopyranosyl bromide (4), 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride (5b), O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl) trichloroacetimidate (7) and ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (8), pent-4-e

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Ishida, Keisuke, Go Hirai, Koji Murakami, et al. "Structure-based design of a selective heparanase inhibitor as an antimetastatic agent." Molecular Cancer Therapeutics 3, no. 9 (2004): 1069–77. http://dx.doi.org/10.1158/1535-7163.1069.3.9.

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Abstract Heparanase is an endo-β-d-glucuronidase that degrades heparan sulfate glycosaminoglycans in the extracellular matrix and the basement membrane and is well known to be involved in tumor cell invasion and angiogenesis. We have focused on heparanase as a target for antitumor agents, especially antimetastatic agents. (R)-3-hexadecanoyl-5-hydroxymethyltetronic acid (RK-682) was found to display an inhibitory activity against heparanase in our screening of natural sources. Because RK-682 has been reported to show inhibitory activities against several enzymes, we have tried to develop select

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