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Relevant bibliographies by topics / Nucleophilic opening

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Academic literature on the topic 'Nucleophilic opening'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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Journal articles on the topic "Nucleophilic opening"

1

Talukdar, Ranadeep. "Synthetically Important Ring-Opening Acylations of Alkoxybenzenes." Synthesis 52, no. 24 (2020): 3764–80. http://dx.doi.org/10.1055/s-0040-1707255.

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AbstractCyclic ketones, anhydrides, lactams and lactones are a particular class of molecules that are often used in synthesis, wherein their electrophilic properties are leveraged to enable facile Friedel–Crafts ring openings through nucleophilic attack at the carbonyl sp2 centre. The use of electron-rich alkoxybenzenes as nucleophiles has also become important since the discovery of the Friedel–Crafts reaction. As a result, various isomeric alkoxybenzenes are used for preparing starting materials in target-oriented syntheses. This review covers the instances of different alkoxybenzenes that a

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2

Rani, Poonam, and Rajendra Srivastava. "Nucleophilic addition of amines, alcohols, and thiophenol with epoxide/olefin using highly efficient zirconium metal organic framework heterogeneous catalyst." RSC Advances 5, no. 36 (2015): 28270–80. http://dx.doi.org/10.1039/c5ra00921a.

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3

Yutilova, Kseniia, Yuliia Bespal’ko, and Elena Shved. "A Computational Study of 2-(chloromethyl)oxirane Ring Opening by Bromide and Acetate Anions Considering Electrophilic Activation with Cations of Alkali Metals." Croatica chemica acta 92, no. 3 (2019): 357–67. http://dx.doi.org/10.5562/cca3505.

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Ring opening of 2-(chloromethyl)oxirane via the nucleophilic substitution with bromide and acetate anions was investigated using density functional theory (DFT) calculations. It was shown that the geometry of the transition states and the activation parameters of the reactions correspond to those of SN2-like mechanism. The nature of localized transition states was analyzed using More O’Ferrall – Jencks plots. The quantum chemical simulations of the potential energy surface for the ring-opening reaction of oxirane by nucleophiles confirmed the theoretical assumptions about the favored path of i

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4

Carramiñana, Victor, Ana M. Ochoa de Retana, Francisco Palacios та Jesús M. de los Santos. "Synthesis of α-Aminophosphonic Acid Derivatives Through the Addition of O- and S-Nucleophiles to 2H-Azirines and Their Antiproliferative Effect on A549 Human Lung Adenocarcinoma Cells". Molecules 25, № 15 (2020): 3332. http://dx.doi.org/10.3390/molecules25153332.

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This work reports a straightforward regioselective synthetic methodology to prepare α-aminophosphine oxides and phosphonates through the addition of oxygen and sulfur nucleophiles to the C–N double bond of 2H-azirine derivatives. Determined by the nature of the nucleophile, different α-aminophosphorus compounds may be obtained. For instance, aliphatic alcohols such as methanol or ethanol afford α-aminophosphine oxide and phosphonate acetals after N–C3 ring opening of the intermediate aziridine. However, addition of 2,2,2-trifluoroethanol, phenols, substituted benzenthiols or ethanethiol to 2H-

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5

Hu, X. Eric. "Nucleophilic ring opening of aziridines." Tetrahedron 60, no. 12 (2004): 2701–43. http://dx.doi.org/10.1016/j.tet.2004.01.042.

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6

Stamm, Helmut. "Nucleophilic ring opening of aziridines." Journal für praktische Chemie 341, no. 4 (1999): 319–31. http://dx.doi.org/10.1002/(sici)1521-3897(199905)341:4<319::aid-prac319>3.0.co;2-9.

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7

Wei, Lan, and William D. Lubell. "Scope and limitations in the use of N-(PhF)serine-derived cyclic sulfamidates for amino acid synthesis." Canadian Journal of Chemistry 79, no. 1 (2001): 94–104. http://dx.doi.org/10.1139/v00-176.

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Ring-opening of N-(PhF)serine-derived cyclic sulfamidate 17 was achieved with different nucleophiles (β-keto esters, β-keto ketones, dimethyl malonate, nitroethane, sodium azide, imidazole, and potassium thiocyanate) to prepare a variety of amino acid analogs. Two different pathways for ring opening of 17 were elucidated: direct nucleophilic displacement, as well as β-elimination followed by Michael addition. Furthermore, β-keto ester and β-keto ketone products 18k,18m, and 18i were converted to prolines and pyrazole amino acids.Key words: glutamate, amino acid, cyclic sulfamidate, proline.

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8

Zhao, Yu, Zitong Zhou, Man Chen, and Weiguang Yang. "Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides." Molecules 26, no. 12 (2021): 3700. http://dx.doi.org/10.3390/molecules26123700.

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N-Sulfonyl amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR spectrometer.

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9

Raheem, Mohammed Abdul, Michael Edmunds, and William Tam. "Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabenzonorbornadienes." Canadian Journal of Chemistry 92, no. 9 (2014): 888–95. http://dx.doi.org/10.1139/cjc-2014-0217.

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The effect of ethyl and methoxycarbonyl substitution on the C1 position of oxabenzonorbornadienes undergoing palladium-catalyzed nucleophilic ring opening was investigated with a variety of aryl iodide nucleophiles. Electron-withdrawing groups in the C1 position or on the aryl iodide afforded lower yields and led to aromatization of products. The presence of an electron-donating group in either position provided high yields in all cases. Despite variances in electronic nature, all trials produced a single regioisomeric product resulting from addition of the aryl group to the olefin carbon fart

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10

Costero, Ana María, Salvador Gil, Margarita Parra, and Pablo Rodríguez. "Unexplored Nucleophilic Ring Opening of Aziridines." Molecules 15, no. 12 (2010): 9135–44. http://dx.doi.org/10.3390/molecules15129135.

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Dissertations / Theses on the topic "Nucleophilic opening"

1

Zahid, Abdul. "Nitrogen heterocycles by tandem cationic cyclisation-aziridinium ion formation-nucleophilic ring opening." Thesis, University of Leeds, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.426848.

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2

Pulipaka, Aravinda B. "Intramolecular ring opening reactions of aziridines by [pi]-nucleophiles /." View abstract, 2008. http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&res_dat=xri:pqdiss&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&rft_dat=xri:pqdiss:3306530.

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3

Diep, Nhut Kiet. "Studies of nucleophile ring opening of oxabicyclic systems in highly polar media application to a total synthesis of antitumor agent, (-)-epothilone B /." Diss., Montana State University, 2006. http://etd.lib.montana.edu/etd/2006/diep/DiepN0806.pdf.

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Polyketides constitute an important family of natural products, having a broad spectrum of biological activity such as antitumor, antibiotic, antifungal, or immunomodulatory action.Â¹ Many of these compounds possess polypropionates (units with alternating hydroxyl and methyl groups), reflecting their common biosynthesis that is found within nature. Their structural complexity and importance of these compounds as therapeutical agents have made them attractive targets for synthetic organic chemists.Â¹ Excellent chiral propionate reagents have been developed over the years,

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4

Watson, Hayley. "Synthesis and reactivity of cyclopropanes and cyclopropenes." Thesis, Loughborough University, 2011. https://dspace.lboro.ac.uk/2134/9032.

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Activated cyclopropanes have been extensively used in synthetic chemistry as precursors for cycloaddition reactions. The rationale behind this is their ability to undergo ring-opening when activated by a Lewis acid, this can be enhanced further by the presence of a carbocation stabilising group like electron-rich aromatics. The stabilised dipole formed after ring opening can be trapped with suitable electrophiles such as imines and aldehydes via a [3+2] cycloaddition reaction. This results in the synthesis of pyrrolidines and tetrahydrofurans in excellent yields but moderate diastereoselectivi

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Foldvari, Zsuzsanna. "Synthetic studies on the C(1)-C(9) unit of TA toxin using nucleophilic opening of chiral epoxides." Pretoria : [s.n.], 2002. http://upetd.up.ac.za/thesis/available/etd-08122005-114153/.

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Miao, Lei. "Synthesis of Amphibian Alkaloids and Development of Acetaminophen Analogues." ScholarWorks@UNO, 2009. http://scholarworks.uno.edu/td/985.

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The focus of these studies has been toward the development of new synthetic methods and procedures for the synthesis of novel compounds with unique biological properties. This research has led to the development of two new synthetic strategies for the construction of two novel amphibian alkaloids. In addition, the efforts have led to the large-scale process for the preparation of a novel analgesic compound. The regioselective ring opening of lactones (δ-valerolactone and γ-butyrolactone) with aryllithium reagents is reported for the construction of a series of δ-hydroxyarylketones and γ-hydrox

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7

Pulipaka, Aravinda B. "Intramolecular Ring Opening Reactions of Aziridines by π-Nucleophiles". Ohio University / OhioLINK, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1205514895.

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Fagnou, Keith. "Rhodium catalysed asymmetric ring opening of oxabicyclic alkenes and diastereoselective ring opening of epoxides with heteroatom nucleophiles." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2000. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape3/PQDD_0015/MQ53360.pdf.

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SUAREZ, BERTOA RICARDO. "Sustainable procedures in organic synthesis." Doctoral thesis, Università degli Studi di Milano-Bicocca, 2009. http://hdl.handle.net/10281/7474.

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O-acyl-N-benzyllactamides are obtained in good yield by reaction of 4-benzyl-5-methyl-1,3-oxazolidine-2,4-diones with Grignards reagents and with lithium alkyls. Three alkanes and two ethers were oxidised with ozone in dichloromethane solution or in aqueous pH 3 suspension. Cyclodecane and cyclododecane were converted into the corresponding cycloalkanones. n-decane was converted into a mixture of isomeric n-decanones and carboxylic acids. An ester was formed from the ethers. Hence, one of the methylene groups of these substrates is generally converted into a carbonyl group. Some of these react

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10

Noël, Amandine. "Etude comparative de la réactivité des β-lactones et β-thiolactones. Synthèse stéréosélective d’α-C- et S-glycosides à partir de dérivés de l’acide N-acétylneuraminique". Thesis, Paris 11, 2012. http://www.theses.fr/2012PA112274/document.

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Les β-lactones étant présentes dans de nombreux composés naturels biologiquement actifs, cette famille de molécules a été intensivement étudiée aussi bien d’un point de vue structural que pour leur réactivité, contrairement aux β-thiolactones. Afin d’établir un parallèle entre ces deux familles, nous avons étudié leur stabilité thermique en comparant les vitesses d’extrusion de CO2 et COS. Le suivi réactionnel a été réalisé par UV-spectrométrie de masse sur des β-lactones di-, tri- et tétrasubstituées et les β-thiolactones correspondantes, dans deux solvants (un polaire, l’autre apolaire). Uti

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Books on the topic "Nucleophilic opening"

1

Ma, Shihong. Nucleophilic ring opening of various oxabicyclic compounds towards cyclohexadienes and cycloheptendols. National Library of Canada, 1993.

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2

Fagnou, Keith. Rhodium catalysed asymmetric ring opening of oxabicyclic alkenes and diastereoselective ring opening of expoxides with heteroatom nucleophiles. National Library of Canada, 2000.

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3

Almas, Jasmine. Rhodium-catalyzed ring opening of vinyl epoxides and vinyl aziridines with aniline nucleophiles. 2002.

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Book chapters on the topic "Nucleophilic opening"

1

Coulembier, Olivier. "Chapter 1. Nucleophilic Catalysts and Organocatalyzed Zwitterionic Ring-opening Polymerization of Heterocyclic Monomers." In Polymer Chemistry Series. Royal Society of Chemistry, 2018. http://dx.doi.org/10.1039/9781788015738-00001.

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2

Bingham, M. J., and M. F. Greaney. "Nucleophilic Ring Opening of Oxetanes." In Alcohols. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00721.

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3

Morey, J. V., and A. E. H. Wheatley. "Synthesis by Nucleophilic Ring Opening." In Alcohols. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00801.

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4

Chanda, A., and V. V. Fokin. "Nucleophilic Opening of Three-Membered Rings." In Water in Organic Synthesis. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-206-00526.

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5

Hapiot, F., and E. Monflier. "Cyclodextrin-Promoted Nucleophilic Opening of Oxiranes." In Water in Organic Synthesis. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-206-00566.

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6

Sapeta, K., and M. A. Kerr. "Rearrangement of Oxazino[3,2-]indazoles by Nucleophilic Ring Opening." In Science of Synthesis Knowledge Updates KU 2011/1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-112-00110.

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7

Bingham, M. J., and M. F. Greaney. "Nucleophilic Ring Opening of Oxetanes with Phosphorus-Stabilized Carbanions." In Alcohols. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00728.

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8

G. Denis, Meakins. "Amines." In Functional Groups. Oxford University Press, 1996. http://dx.doi.org/10.1093/hesc/9780198558675.003.0010.

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This chapter points out that ethers are ideal solvents for many reactions, but only special types of ethers can be regarded as reagents, such as the atmospheric O<sub>2</sub> that reacts slowly with ethers by a radical mechanism to give highly explosive peroxides. It highlights that splitting simple ethers, two primary alkyl groups, requires vigorous treatment with the strongly nucleophilic hydroiodic acid. The nucleophilic attack occurs at the C which is less hindered and less negative. The chapter explains that the alternative ring opening occurs with protonated oxiran. It describes a method

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9

Davis, Benjamin G., and Antony J. Fairbanks. "Reactions of the anomeric centre Part II." In Carbohydrate Chemistry. Oxford University Press, 2002. http://dx.doi.org/10.1093/hesc/9780198558330.003.0005.

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This chapter focuses on reactions that are particular to the anomeric centre of a free sugar which is hemiacetal and explains how the mechanisms by which nucleophilic substitution at the anomeric centre may occur. It describes the problem of control of stereochemistry at the anomeric centre and the use of neighbouring group participation. This allows for the formation of 1,2-trans glycosides. It also clarifies how to form anomeric bromides and illustrates their substitution reaction chemistry. The chapter discusses nucleophilic addition reactions to sugars which occur via the trapping of the f

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Sethiya, Ayushi, Nusrat Sahiba, and Shikha Agarwal. "Role of Click Chemistry in Organic Synthesis." In Current Topics in Chirality - From Chemistry to Biology. IntechOpen, 2021. http://dx.doi.org/10.5772/intechopen.96146.

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Click chemistry involves highly efficient organic reactions of two or more highly functionalized chemical entities under eco-benign conditions for the synthesis of different heterocycles. Several organic reactions such as nucleophilic ring-opening reactions, cyclo-additions, nucleophilic addition reactions, thiol-ene reactions, Diels Alder reactions, etc. are included in click reactions. These reactions have very important features i.e. high functional group tolerance, formation of a single product, high atom economy, high yielding, no need for column purification, etc. It also possesses sever

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Conference papers on the topic "Nucleophilic opening"

1

"Ring Opening of Epoxides by Nucleophiles in Nitromethane without any Catalyst at Room Temperature." In 3rd International Conference on Biological, Chemical and Environmental Sciences. International Institute of Chemical, Biological & Environmental Engineering, 2015. http://dx.doi.org/10.15242/iicbe.c0915048.

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2

Vázquez-Tato, M. Pilar, Julio Seijas, Xesús Feás, and Sandra Labandeira-Peteiro. "Synthesis of triols with C₃ symmetry by ring opening of tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione with nucleophiles." In The 15th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00690.

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