Relevant bibliographies by topics / Acid-catalysed rearrangement

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  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Acid-catalysed rearrangement'

Author: Grafiati
Published: 5 June 2025
Last updated: 1 August 2025

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Journal articles on the topic "Acid-catalysed rearrangement"

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Urban, S., and RJ Capon. "Marine Sesquiterpene Quinones and Hydroquinones: Acid-Catalyzed Rearrangements and Stereochemical Investigations." Australian Journal of Chemistry 47, no. 6 (1994): 1023. http://dx.doi.org/10.1071/ch9941023.

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Acid treatment of both ilimaquinone (3) and 5-epi-ilimaquinone (9) yielded the same rearrangement products, (7) and (8), thus defining a common absolute stereochemistry. Likewise, acid- catalysed rearrangement of avarol (10) and arenarol (11) yielded the common product aureol (13), allowing the absolute stereochemistry of arenarol (11) and its related quinone arenarone (12) to be assigned. This latter acid- catalysed rearrangement also yielded an unexpected electrophilic aromatic cyclization product (15), the dimethyl ether (17) of which could be obtained in quantitative yield from acid treatm
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2

Shubina, Tatyana E., and Timothy Clark. "Catalysis of the Quadricyclane to Norbornadiene Rearrangement by SnCl2 and CuSO4." Zeitschrift für Naturforschung B 65, no. 3 (2010): 347—r369. http://dx.doi.org/10.1515/znb-2010-0319.

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Ab initio and density-functional theory (DFT) calculations have been used to investigate the model rearrangements of quadricyclane to norbornadiene catalysed by single CuSO4 and SnCl2 molecules. The isolated reactions with the two molecular catalysts proceed via electron-transfer catalysis in which the hydrocarbon is oxidised, in contrast to systems investigated previously in which the substrate was reduced. The even-electron SnCl2-catalysed reaction shows singlet-triplet two-state reactivity. Solvation by a single methanol molecule changes the mechanism of the rearrangement to a classical Lew
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Tsui, Wing-Yan, and Geoffrey Brown. "Acid-catalysed rearrangement of caryophyllene oxide." Journal of the Chemical Society, Perkin Transactions 1, no. 20 (1996): 2507. http://dx.doi.org/10.1039/p19960002507.

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Lee-Ruff, E., and Fred J. Ablenas. "Acid-catalyzed rearrangement of cyclobutanols. A novel rearrangement." Canadian Journal of Chemistry 65, no. 7 (1987): 1663–67. http://dx.doi.org/10.1139/v87-278.

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The acid-catalysed dehydration–rearrangement reaction of α-thienyl cyclobutanols 3 and 4 resulted in the formation of tetrahydronaphtho[2,3-b]thiophenes 5a and 6a. The rearrangement to the linearly fused PAH system instead of the expected angularly fused system reflects α-scission of the cyclobutyl ring. A mechanism based on deuterium labelling studies is proposed to account for the product formation.
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Maryasin, Boris, Dainis Kaldre, Renan Galaverna, et al. "Unusual mechanisms in Claisen rearrangements: an ionic fragmentation leading to a meta-selective rearrangement." Chemical Science 9, no. 17 (2018): 4124–31. http://dx.doi.org/10.1039/c7sc04736c.

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A mechanistic investigation of the acid-catalysed redox-neutral arylation of ynamides intertwining ESI-MS, DFT and experiments reveals diverse pathways available from an otherwise simple-looking transformation.
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K. Banerjee, Ajoy, and Hector E. Hurtado S. "Acid catalysed novel rearrangement of bicyclic dienone." Tetrahedron 41, no. 15 (1985): 3029–32. http://dx.doi.org/10.1016/s0040-4020(01)96654-2.

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Vishwakarma, R. A. "Spiroforskolin : Acid-catalysed rearrangement product of forskolin." Tetrahedron Letters 30, no. 1 (1989): 131–32. http://dx.doi.org/10.1016/s0040-4039(01)80343-9.

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Araneda, Juan F., Warren E. Piers, Michael J. Sgro, and Masood Parvez. "Bronsted acid-catalyzed skeletal rearrangements in polycyclic conjugated boracycles: a thermal route to a ladder diborole." Chem. Sci. 5, no. 8 (2014): 3189–96. http://dx.doi.org/10.1039/c4sc01201a.

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Wilshire, JFK. "The Phthalimidomethyl Rearrangement." Australian Journal of Chemistry 43, no. 11 (1990): 1817. http://dx.doi.org/10.1071/ch9901817.

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The discovery of a new acid-catalysed monodentate N → C aromatic rearrangement, namely the phthalimidomethyl rearrangement, is reported. In this rearrangement, discovered during the reaction of N-hydroxymethylphthalimide with certain alkyl N-(4-nitrophenyl)carbamates in concentrated sulfuric acid solution, the phthalimidomethyl group migrates from its initial location on the nitrogen atom of the carbamate function to a carbon atom of the nitrophenyl group. Evidence, provided by an appropriate 'crossover' experiment, indicates that the rearrangement is intermolecular. Hindered rotation about th
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10

Koskinen, Ari M. P., Luis Muñoz, and Kari Rissanen. "Unexpected acid-catalysed rearrangement of a vinylcyclopropane derivative." J. Chem. Soc., Chem. Commun., no. 6 (1993): 491–92. http://dx.doi.org/10.1039/c39930000491.

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Dissertations / Theses on the topic "Acid-catalysed rearrangement"

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Cambridge, James R. A. "Lewis acid catalysed rearrangement of epoxides :a mechanistic study." Thesis, University of Canterbury. Chemistry, 2004. http://hdl.handle.net/10092/5646.

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The Lewis acid catalysed rearrangement of optically active, deuterium labelled styrene oxide derivatives to aldehydes is studied experimentally and the mechanism is further elucidated by ab initio molecular orbital and density functional calculations. The Lewis acid catalysed rearrangement of styrene oxide derivatives is shown to occur via a carbocation intermediate. Opening of the epoxide ring occurs with rotation of the Lewis acid coordinated oxygen either towards or away from the aryl group to form either the cis or trans carbocation. Calculations indicate that conversion between the cis an
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Nam, Shayne G. C. "The mechanism of Lewis acid catalysed epoxide rearrangement to aldehyde." Thesis, University of Canterbury. Chemistry, 2005. http://hdl.handle.net/10092/6091.

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This thesis describes investigations centred on the mechanistic pathway of the Lewis acid-promoted conversion of epoxides into aldehydes. Such studies were directed to gain new information about this important, fundamental rearrangement which contributes to our knowledge and understanding of how and why chemical reactions occur. The research undertaken involved the use of deuterium labelling studies working with enantio-enriched epoxides. Chapter One reviews previous literature and the results of previous mechanistic studies into the Lewis acid catalysed rearrangements of epoxides. Chapter T
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Owston, Nathan Ashley. "Novel transition metal-catalysed syntheses of carboxylic acid derivatives." Thesis, University of Bath, 2008. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.512253.

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This thesis describes the chemistry developed during a study of novel transition metalcatalysed reactions for the synthesis of carboxylic acid derivatives. Chapter 2 describes a novel protocol for the synthesis of primary amides from alcohols in one-pot where a metal complex mediates two fundamentally different catalytic processes. An iridium catalyst has been shown to be effective for the selective rearrangement of aldoximes into primary amides. In addition, an iridium-catalysed oxidation of activated alcohols via hydrogen transfer has been developed using an alkene as formal oxidant. These r
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Albers, Lena Verfasser], Thomas [Akademischer Betreuer] [Müller, and Rüdiger [Akademischer Betreuer] Beckhaus. "Mechanistic investigations on Lewis acid-catalysed skeletal rearrangement reactions of polysilanes and germapolysilanes : subtle capture of intermediates / Lena Albers. Betreuer: Thomas Müller ; Rüdiger Beckhaus." Oldenburg : BIS der Universität Oldenburg, 2015. http://d-nb.info/1084187159/34.

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Albers, Lena [Verfasser], Thomas [Akademischer Betreuer] Müller, and Rüdiger [Akademischer Betreuer] Beckhaus. "Mechanistic investigations on Lewis acid-catalysed skeletal rearrangement reactions of polysilanes and germapolysilanes : subtle capture of intermediates / Lena Albers. Betreuer: Thomas Müller ; Rüdiger Beckhaus." Oldenburg : BIS der Universität Oldenburg, 2015. http://d-nb.info/1084187159/34.

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Book chapters on the topic "Acid-catalysed rearrangement"

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Kirby, A. J. "Rearrangements and fragmentations." In Stereoelectronic Effects. Oxford University Press, 1996. http://dx.doi.org/10.1093/hesc/9780198558934.003.0007.

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This chapter addresses two groups of reactions of synthetic importance and mechanistic interest, where the key interactions are through two or three bonds: fragmentations and rearrangements. Fragmentation reactions are observed when a strong electron donor interacts with a good leaving group three carbons away. The simplest case is the acid-catalysed fragmentation of a 1,3-diol to an alkene and a ketone or aldehyde. The addition of a nucleophile to a carbonyl group is a simple way to generate a donor oxyanion, and where the addition is sufficiently selective, clean reactions are observed. Mean
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Ward, Robert S. "Reactions of diols." In Bifunctional Compounds. Oxford University Press, 1994. http://dx.doi.org/10.1093/hesc/9780198558088.003.0004.

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This chapter describes 1,2-diols that undergo acid-catalysed rearrangement to afford ketones, which is a general reaction that involves the generation of a carbocation intermediate. It refers to the driving force of the general reaction of 1,2-diols that is provided by the resonance stabilization of the resulting carbocation. It also explains how diols react with aldehydes and ketones under anhydrous conditions to give acetals and ketals, which is a reaction that is acid-catalysed and proceeds most readily when the heterocyclic ring formed is five- or six-membered. The chapter discusses a tran
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Wovkulich, P. M., K. Shankaran, J. Kigiel, and M. R. Uskokovic,. "Total Synthesis of 1233A." In Exercises in Synthetic Organic Chemistry. Oxford University PressOxford, 1997. http://dx.doi.org/10.1093/oso/9780198559443.003.0027.

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Abstract Discussion. Points Total Synthesis of 1233A What is the mechanism of the Noyori catalyst-mediated asymmetric hydrogenation step a? Explain the diastereoselectivity observed in the [2,3]-rearrangement of step i. During the hydroboration step, a substantial amount of compound 13 was formed. Suggest a way to convert it into the desired epimer 8 by exploiting the latent symmetry of the system. Further Reading For the influence of trace amount of acid in the ruthenium (11)-BINAP catalysed asymmetric hydrogenation, see: S. A. King, A. S. Thompson, A. O. King and R. T. Verhoeven, J. Org. Che
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Harwood, Laurence M. "Acid catalysed aromatic rearrangements." In Polar Rearrangements. Oxford University Press, 1992. http://dx.doi.org/10.1093/hesc/9780198556701.003.0006.

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This chapter reviews arbitrary distinction to create the classification of aromatic rearrangements. It considers reactions that are initiated by the generation of an arenium ion and involve migration around the aromatic ring or from a side chain onto the aromatic nucleus. It also points out that the migration terminus positioned on an aromantic ring is initiated by protonation or by a Lewis acid, which is commonly a consequence of equilibration to form thermodynamically stable products. The chapter highlights intramolecular migration, which occurs via a π-complex that leads to equilibration be
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Hwu, J. R., and J. M. Wetzel,. "Total Synthesis of (—)-Solavetivone." In Exercises in Synthetic Organic Chemistry. Oxford University PressOxford, 1997. http://dx.doi.org/10.1093/oso/9780198559443.003.0023.

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Abstract Discussion Points Suggest a mechanism for step d. The conversion of compound 6 into the tri none 7 was carried out in a single oxidative step. Propose alternative methods for the introduction of α, β unsaturation in a ketone. What factors govern the regioselectivity and stereoselectivity of the conjugate additon of the trimethylsilyl nucleophile in step g? A homonuclear NMR decoupling experiment was carried out on compound 11, simultaneously irradiating the two proton signals at δ 4.69 and 4.70 ppm. This resulted in the simplification of the single proton multiplet between δ 2.35–2.87
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Journal articles
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