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Journal articles on the topic 'Acid-catalysed rearrangement'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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11

C., BHAKTA. "Methanolic Sodium Acetate Catalysed Rearrangement of 4-Acylisocoumarins into 3-Alkylisocoumarins." Journal of Indian Chemical Society Vol. 62, May 1985 (1985): 380–82. https://doi.org/10.5281/zenodo.6302986.

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Department of Chemistry, Patna University, Patna-800 005 <em>Manuscript received 16 August 1984, accepted 29 April 1985</em> 4-Bromoacetylisocoumarin (4) prepared from 4-carboxyisocoumarin (2) on treatment with sodium acetate in acetic acid afforded 4-acetoxyacetylisocoumarin (5), while that with methanolic sodium acetate yielded 3-acetoxymethylisocoumarin (9) \(v\)ia rearrangement 4-Acetylisocoumarin (3) underwent similar rearrangement to 3-methylisocoumarin (7). Acid catalysed hydrolysis of (5) afforded the dioxene (18).

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12

Chinta, Bhavani Shankar, Soniya Gandhi, and Beeraiah Baire. "Acid catalysed rearrangement of isobenzofurans to angularly fused phthalides." Organic & Biomolecular Chemistry 17, no. 19 (2019): 4715–19. http://dx.doi.org/10.1039/c9ob00708c.

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An acid catalysed, cascade process for the construction of angularly fused polycyclic phthalides from isobenzofurans via a simultaneous ring closing–ring opening cascade has been reported. This approach serves as a greener alternative for the angularly fused polycyclic phthalides.

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13

Thopate, Shankar Ramchandra, Santosh Rajaram Kote, Sandeep Vasantrao Rohokale, and Nitin Madhukar Thorat. "Citric acid catalysed Beckmann rearrangement, under solvent free conditions." Journal of Chemical Research 35, no. 2 (2011): 124–25. http://dx.doi.org/10.3184/174751911x557296.

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14

Kozhevnikova, E. "Fries rearrangement of aryl esters catalysed by heteropoly acid." Applied Catalysis A: General 245, no. 1 (2003): 69–78. http://dx.doi.org/10.1016/s0926-860x(02)00618-x.

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15

Srikrishna, Adusumilli, Kathiresan Krishnan та Somepalli Vankateswarlu. "Acid-catalysed thermal rearrangement of γ,δ-unsaturated ketones". J. Chem. Soc., Chem. Commun., № 2 (1993): 143–45. http://dx.doi.org/10.1039/c39930000143.

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16

Liu, Rong-Ming, Xavier F. D. Chillier, Philippe Kamalaprija, Ulrich Burger, and Fazil O. Gülaçar. "Acid-Catalysed Backbone Rearrangement of cholesta-6,8(14)-dienes." Helvetica Chimica Acta 79, no. 4 (1996): 989–98. http://dx.doi.org/10.1002/hlca.19960790407.

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17

Hanson, James R. "The General Dienol: Benzene Rearrangement of Ring a of the Steroids." Journal of Chemical Research 2005, no. 3 (2005): 141–46. http://dx.doi.org/10.3184/0308234054213663.

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The dienol: benzene type of rearrangement of steroids, to form compounds with an aromatic ring A, occurs under acid-catalysed conditions with a wide range of substrates containing two double bond equivalents and a carbonium ion source on rings A and B.

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18

Peakman, Torren M., та James R. Maxwell. "Acid-catalysed rearrangements of steroid alkenes. Part 1. Rearrangement of 5α-cholest-7-ene". J. Chem. Soc., Perkin Trans. 1, № 5 (1988): 1065–70. http://dx.doi.org/10.1039/p19880001065.

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19

Jackson, Anthony H., Werawat Lertwanawatana, Ravindra K. Pandey та K. R. Nagaraja Rao. "Mechanism of the acid-catalysed rearrangement of α-free pyrromethanes". J. Chem. Soc., Perkin Trans. 1, № 2 (1989): 374–75. http://dx.doi.org/10.1039/p19890000374.

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20

Geetha, Natarajan, and Kalpattu Kuppusamy Balasubramanian. "Trifluoroacetic acid catalysed [1,3]-rearrangement of aryl 2-halocyclohexenylmethyl ethers." Tetrahedron Letters 39, no. 11 (1998): 1417–20. http://dx.doi.org/10.1016/s0040-4039(97)10780-8.

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21

Elings, Jacob A., Hans E. B. Lempers та Roger A. Sheldon. "Solid-Acid Catalysed Rearrangement of Cyclic α,β-Epoxy Ketones". European Journal of Organic Chemistry 2000, № 10 (2000): 1905–11. http://dx.doi.org/10.1002/(sici)1099-0690(200005)2000:10<1905::aid-ejoc1905>3.0.co;2-o.

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22

Abu-Namous, Adel M. A., John H. Ridd, and John P. B. Sandall. "15N Nuclear polarisation in the rearrangement of 2,6-dichloro-N-nitroaniline and 2,6-dibromo-N-nitroaniline." Canadian Journal of Chemistry 64, no. 6 (1986): 1124–29. http://dx.doi.org/10.1139/v86-188.

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The acid-catalysed rearrangements of 2,6-dichloro-N-nitroaniline and 2,6-dibromo-N-nitroaniline to give the corresponding 4-nitro derivatives have been followed by 1H and 15N nmr spectroscopy in deuteriochloroform at 30 °C. When 15NO2-labelled nitramines are used, the 15N nmr signals for both the substrate and product show enhanced absorption during reaction. When one labelled nitramine and one unlabelled nitramine are rearranged together, isotopic exchange occurs and 15N nmr signals are seen for both substrates and both products. For the initially unlabelled nitramine and its product, these s

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23

Sankar, P. Dey, and K. Dey Dilip. "Acid-catalysed rearrangements of allyl 4-hydroxybenzoate and 3-methylbut-2- enyl-4-hydroxybenzoate." Journal of Indian Chemical Society Vol. 86, May 2009 (2009): 485–87. https://doi.org/10.5281/zenodo.5810153.

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Department of Chemistry, Srikrishna College, Bagula-741 507, Nadia, West Bengal, India <em>E-mail</em> : deysp2002@yahoo.co.in Department of Chemistry, Chandidas Mahavidyalaya, Khujutipara-731 215, Birbhum, West Bengal, India <em>E-mail </em>: deydk@yahoo.com <em>Manuscript received 27 June 2008, revised 31 December 2008, accepted 1 January 2009</em> On treatment with 75% polyphosphoric acid or TFA-H<sub>2</sub>SO<sub>4</sub> (50%) allyl 4-hydroxybenzoate and 3-methylbut-2-enyl-4-hydroxybenzoate afforded 4-hydroxy-3-(2<em>'</em> -hydroxypropyl)benzoic acid and 4-hydroxy-3-(3<em>'</em>

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24

Cambie, RC, RA Franich, D. Larsen, PS Rutledge, GR Ryan, and PD Woodgate. "Potential Ambergris Odorants From Abietic Acid." Australian Journal of Chemistry 43, no. 1 (1990): 21. http://dx.doi.org/10.1071/ch9900021.

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In contrast to literature reports the rearrangement of abietic acid (1) catalysed by 96% sulfuric acid gives a mixture (3 : 1) of two dienoic acids (19) and (27) whose structures have been established by spectral means. Compounds containing the diene system are unstable, severely limiting their use in synthesis. However, removal of the diene functionality affords stable compounds which, despite difficulties in stereochemical control, are suitable for further modification. The synthesis of compounds containing a five- membered C-ring common to a class of potential amber odorants is reported.

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25

Larsen, Kim, Carl Erik Olsen, and Mohammed Saddik Motawia. "Acid-catalysed rearrangement of glycosyl trichloroacetimidates: a novel route to glycosylamines." Carbohydrate Research 343, no. 2 (2008): 383–87. http://dx.doi.org/10.1016/j.carres.2007.10.019.

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26

P., N. GUPTA, and RAINA ANJU. "Electrochemical Behaviour of Symmetrically Disubstituted Azobenzene in Buffered Media." Journal of Indian Chemical Society Vol. 66, DEC 1989 (1989): 865–67. https://doi.org/10.5281/zenodo.6009248.

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Department of Chemistry, University of Kashmir, Srinagar-190 006 <em>Manuscript received 5 January 1989, accepted 22 July 1989</em> Redaction behaviour of 2.2<em>'</em>-dichloroazobenzene and 2,2<em>'</em>-dlmetbylazobenze in well buffered media over a broad pH range has been investigated employing various electrochemical techniques. Depending upon pH, rearrangement and disproportionation (acid-catalysed) of hydrazo intermediates have been highlighted as possible mechanistic pathway.

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27

Davis, BR, SJ Johnson, and PD Woodgate. "Diterpene Synthesis. IV. Synthesis of Some Octahydrophenanthrenes and a Contribution to the Mechanisms of Cyclialkylations." Australian Journal of Chemistry 40, no. 7 (1987): 1283. http://dx.doi.org/10.1071/ch9871283.

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The cis octahydrophenanthrene (3), a product of the acid-catalysed cyclialkylation of alcohol (1), has been synthesized. Various analogues having cis A/B stereochemistry have also been isolated from cyclization reactions; in these cases there is no rearrangement of the carbon skeleton, as shown by isotopic labelling. Variable temperature n.m.r. studies have been used to define the conformations of some of the cis octahydrophenanthrenes. The mechanisms of cyclialkylations leading to octahydrophenanthrenes can now be clarified.

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28

Kuriakose, Sunny, and V. N. Rajasekharan Pillai. "Polyethyleneglycol-catalysed benzil-benzilic acid rearrangement: A reaction in soluble macromolecular cavities." Proceedings / Indian Academy of Sciences 106, no. 1 (1994): 59–64. http://dx.doi.org/10.1007/bf02867594.

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29

Reddy, N. Srinivasa, T. Venkateshwar Goud та Y. Venkateswarlu. "Acid catalysed rearrangement of Δ^9,15-africanene: a cytotoxic sesquiterpene". Journal of Chemical Research 2000, № 9 (2000): 438–39. http://dx.doi.org/10.3184/030823400103167994.

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30

Srikrishna, A., G. Satyanarayana, and P. Ravi Kumar. "Enantiospecific synthesis of tricyclo[5.2.1.04,8]decanes via acid catalysed rearrangement of isotwistanes." Tetrahedron Letters 47, no. 3 (2006): 363–66. http://dx.doi.org/10.1016/j.tetlet.2005.11.008.

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31

Mlinarić-Majerski, Kata, Goran Kragol, Marija Šindler-Kulyk, and Dražen Pavlović. "Acid-catalysed rearrangement of tetracyclo[4.3.0.02,9.04,8]nonane skeleton to substituted brendene derivatives." Liebigs Annalen 1995, no. 10 (1995): 1885–89. http://dx.doi.org/10.1002/jlac.1995199510264.

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32

Hodgson, David M., and Hasanain A. A. Almohseni. "Evolution of a Cycloaddition–Rearrangement Approach to the Squalestatins: A Quarter-Century Odyssey." Synlett 31, no. 16 (2020): 1555–72. http://dx.doi.org/10.1055/s-0040-1707127.

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The highs, lows, and diversions of a journey leading to two syntheses of 6,7-dideoxysqualestatin H5 is described. Both syntheses relied on highly diastereoselective n-alkylations of a tartrate acetonide enolate and subsequent oxidation–hydrolysis to provide an asymmetric entry to β-hydroxy-α-ketoester motifs. The latter were differentially elaborated to diazoketones which underwent stereo- and regioselective Rh(II)-catalysed cyclic carbonyl ylide formation–cycloaddition and then acid-catalysed transketalisation to generate the 2,8-dioxabicyclo[3.2.1]octane core of the squalestatins/zaragozic a

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33

Hanson, James R. "Skeletal Rearrangements of Rings C and D of the Kaurene and Beyerene Tetracyclic Diterpenoids." Journal of Chemical Research 42, no. 4 (2018): 175–80. http://dx.doi.org/10.3184/174751918x15233039624478.

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The skeletal rearrangement of the bicyclo[3.2.1]octane portion of rings C and D of the kaurene and beyerene tetracyclic diterpenoids are reviewed, revealing the tendency of the secondary carbocations to rearrange to tertiary carbocations with the eventual preferential formation of bicyclo[2.2.2]octanes. Under acid-catalysed conditions the variations in the products with the nucleophilicity of the counter ions suggest that the intervention of discrete rather than completely delocalised non-classical carbonium ions may be contributing to the reaction pathway.

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34

Yin, Biao-Lin, Yikang Wu, and Yu-Lin Wu. "Acid catalysed rearrangement of a spiroketal enol ether. An easy synthesis of chrycorin." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (July 5, 2002): 1746–47. http://dx.doi.org/10.1039/b205229f.

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35

Fariña, Francisco, M. Carmen Paredes, and Jaime A. Valderrama. "Perkin communications. Acid-catalysed rearrangement of the Diels–Alder adducts of activated quinones." J. Chem. Soc., Perkin Trans. 1, no. 8 (1990): 2345–46. http://dx.doi.org/10.1039/p19900002345.

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36

Enev, Valentin St, and Elena T. Tsankova. "Lewis acid catalysed rearrangement of 7,11-epoxyisogermacrone. Formation of a new carbon skeleton." Tetrahedron 47, no. 32 (1991): 6399–406. http://dx.doi.org/10.1016/s0040-4020(01)86568-6.

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37

Kozhevnikova, E. "Fries rearrangement of aryl esters catalysed by heteropoly acid: catalyst regeneration and reuse." Applied Catalysis A: General 260, no. 1 (2004): 25–34. http://dx.doi.org/10.1016/j.apcata.2003.10.008.

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38

Kumar, M. Srinivas Lavanya, Sudipta Kumar Manna, Saroj Maji та Gautam Panda. "Indium triflate catalysed 3-aza-Cope rearrangement of amino acid derived α,β-unsaturated esters to alkylidene oxindoles". Organic & Biomolecular Chemistry 15, № 8 (2017): 1762–66. http://dx.doi.org/10.1039/c6ob02419j.

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39

Stephenson, GR, DA Owen, H. Finch та S. Swanson. "The Role of the Substituent Pattern in Determining Selectivity in the Preparation of Tricarbonyl(η5-cyclohexadienyl)iron(1+) Salts by Acid-Catalyzed Demethoxylation". Australian Journal of Chemistry 45, № 1 (1992): 121. http://dx.doi.org/10.1071/ch9920121.

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The factors that determine the selectivity of the acid-catalysed dealkoxylation of unsymmetrically substituted tricarbonyl(η4-alkoxycyclohexa-1,3-diene)iron(0) complexes have been investigated. Regioselective demethoxylation of complexes with a variety of substitution patterns has indicated that the selectivity arises from differences in the stabilization of the reaction intermediates and transition states by the diene substituents on the π-bound ligand. The observed regioisomers correspond to the product of the most stabilized intermediate pathway, rather than the product of minimum rearrange

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40

Rao, GSRS, DK Banerjee, LU Devi, and U. Sheriff. "Synthesis Based on Cyclohexadienes. 5. A New Approach to the Synthesis of a-Ring Aromatic Steroids - a Formal Total Synthesis of (+/-)-Estrone." Australian Journal of Chemistry 45, no. 1 (1992): 187. http://dx.doi.org/10.1071/ch9920187.

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A new strategy for the construction of A-ring aromatic steroids which resulted in the formal total synthesis of estrone is described. Thus reaction of the adduct (9), obtained from 1-methoxy-4-methylcyclohexa-1,4-diene and acrolein , with 3-(m-methoxypheny1) propyl -magnesium bromide followed by oxidation afforded the bicyclo [2.2.2] octene derivative (14). Acid-catalysed rearrangement of (14) followed by an intramolecular Michael addition resulted in the cis tetraenone (18) which was dehydrogenated with palladium chloride to the pentaenone (22). Li/NH3 reduction of (22) gave 3-methoxy-D-homoe

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41

Peakman, Torren M., Karen Ellis, and James R. Maxwell. "Acid-catalysed rearrangements of steroid alkenes. Part 2. A re-investigation of the backbone rearrangement of cholest-5-ene." Journal of the Chemical Society, Perkin Transactions 1, no. 5 (1988): 1071. http://dx.doi.org/10.1039/p19880001071.

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42

Hannaby, Malcolm, and Stuart Warren. "Alkyl migration in competition with phenylthio migration in the acid-catalysed rearrangement of alcohols." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (1992): 3007. http://dx.doi.org/10.1039/p19920003007.

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43

Oliveira, Ana M. A. G., Ana M. F. Oliveira-Campos, M. Manuela M. Raposo, John Griffiths, and Antonio E. H. Machado. "Fries rearrangement of dibenzofuran-2-yl ethanoate under photochemical and Lewis-acid-catalysed conditions." Tetrahedron 60, no. 29 (2004): 6145–54. http://dx.doi.org/10.1016/j.tet.2004.05.060.

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44

Buncel, Erwin, and Kap-Soo Cheon. "Acid-catalysed disproportionation and benzidine rearrangement of phenylhydrazinopyridines: reaction pathways, kinetics and mechanism 1." Journal of the Chemical Society, Perkin Transactions 2, no. 5 (1998): 1241–48. http://dx.doi.org/10.1039/a708485d.

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45

Hamel, Pierre, Yves Girard, Joseph G. Atkinson, and Michael A. Bernstein. "Unexpected acid-catalysed rearrangement of certain 3-(arylthio)indoles to 2-(2-aminophenyl)benzothiophenes." Journal of the Chemical Society, Chemical Communications, no. 16 (1990): 1072. http://dx.doi.org/10.1039/c39900001072.

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46

Cecchini, Cristina, Franco D'Onofrio, and Giovanni Piancatelli. "Synthesis of 2-furylcarbinol derivatives by an acid-catalysed rearrangement of 2,5-dimethoxy-2,5-dihydrofurans." Tetrahedron Letters 34, no. 49 (1993): 7957–60. http://dx.doi.org/10.1016/s0040-4039(00)61522-8.

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47

Kammermeier, Stefan, Peter Siemsen, Paul Seiler, François Diederich, and Rik R. Tykwinski. "Synthesis of a highly strained permethylenated cycloocta-1,5-diyne derivative by acid-catalysed thermal rearrangement." Chemical Communications, no. 12 (1998): 1285–86. http://dx.doi.org/10.1039/a802927j.

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48

Fanning, Kate N., Andrew G. Jamieson та Andrew Sutherland. "Stereoselective β-hydroxy-α-amino acid synthesis via an ether-directed, palladium-catalysed aza-Claisen rearrangement". Organic & Biomolecular Chemistry 3, № 20 (2005): 3749. http://dx.doi.org/10.1039/b510808j.

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49

Ghigo, Giovanni, Andrea Maranzana, and Glauco Tonachini. "A change from stepwise to concerted mechanism in the acid-catalysed benzidine rearrangement: a theoretical study." Tetrahedron 68, no. 9 (2012): 2161–65. http://dx.doi.org/10.1016/j.tet.2012.01.014.

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50

Hricovı́niová-Bı́liková, Zuzana, and Ladislav Petruš. "Synthesis of sedoheptulose from 2-C-(hydroxymethyl)-d-allose by molybdic acid-catalysed carbon-skeleton rearrangement." Carbohydrate Research 320, no. 1-2 (1999): 31–36. http://dx.doi.org/10.1016/s0008-6215(99)00133-0.

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