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Journal articles on the topic 'Catalysed rearrangement'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Shubina, Tatyana E., and Timothy Clark. "Catalysis of the Quadricyclane to Norbornadiene Rearrangement by SnCl2 and CuSO4." Zeitschrift für Naturforschung B 65, no. 3 (March 1, 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 Lewis acid-base process.

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2

Kona, Chandrababu Naidu, and Chepuri V. Ramana. "Gold(i)-catalysed [1,3] O→C rearrangement of allenyl ethers." Chem. Commun. 50, no. 17 (2014): 2152–54. http://dx.doi.org/10.1039/c3cc49629e.

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Gold standard: a simple and rapid access to the α-substituted acryl aldehydes has been provided by developing a gold-catalysed [1,3] rearrangement of the allenyl ethers importantly with a record turnover frequency = 4600 h⁻¹ (at 0.05 mol% of the catalyst concentration) in homogeneous gold(i) catalysis.

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3

Song, Wangze, Yu Zhao, John C. Lynch, Hyunjin Kim, and Weiping Tang. "Divergent de novo synthesis of all eight stereoisomers of 2,3,6-trideoxyhexopyranosides and their oligomers." Chemical Communications 51, no. 98 (2015): 17475–78. http://dx.doi.org/10.1039/c5cc07787g.

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All eight possible stereoisomers of 2,3,6-trideoxyhexopyranosides are prepared systematically from furan derivatives by a sequence of Achmatowicz rearrangement, Pd-catalysed glycosidation, and chiral catalyst-controlled tandem reductions.

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4

Fanning, Kate, Andrew Jamieson, and Andrew Sutherland. "Palladium(II)-Catalysed Rearrangement Reactions." Current Organic Chemistry 10, no. 9 (June 1, 2006): 1007–20. http://dx.doi.org/10.2174/138527206777435490.

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5

Srivastava, Vishnu P., Rajesh Patel, Garima, and Lal Dhar S. Yadav. "Cyclopropenium ion catalysed Beckmann rearrangement." Chemical Communications 46, no. 31 (2010): 5808. http://dx.doi.org/10.1039/c0cc00815j.

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6

Yang, Shen K. "Base-catalysed rearrangement of temazepam." Journal of Pharmaceutical and Biomedical Analysis 12, no. 2 (February 1994): 209–19. http://dx.doi.org/10.1016/0731-7085(94)90032-9.

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7

Nakamura, Itaru, Mao Owada, Takeru Jo, and Masahiro Terada. "Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines." Beilstein Journal of Organic Chemistry 14 (July 31, 2018): 1972–79. http://dx.doi.org/10.3762/bjoc.14.172.

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A cationic cobalt catalyst efficiently promoted the reaction of N-alkoxycarbonyloxyanilines at 30 °C, affording the corresponding ortho-aminophenols in good to high yields. As reported previously, our mechanistic studies including oxygen-18 labelling experiments indicate that the rearrangement of the alkoxycarbonyloxy group proceeds in [1,3]-manner. In this article, we discuss the overall picture of the cobalt-catalysed [1,3]-rearrangement reaction including details of the reaction conditions and substrate scope.

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8

Davies, Paul W., Nicolas Martin, and Neil Spencer. "Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines." Beilstein Journal of Organic Chemistry 7 (June 21, 2011): 839–46. http://dx.doi.org/10.3762/bjoc.7.96.

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Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using 13C-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against the reaction of a range of 13C- and deuterium-labelled substrates.

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9

Lee-Ruff, E., and Fred J. Ablenas. "Acid-catalyzed rearrangement of cyclobutanols. A novel rearrangement." Canadian Journal of Chemistry 65, no. 7 (July 1, 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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10

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 treatment of avarol dimethyl ether (16).

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11

Eichinger, PCH, and JH Bowie. "Carbanion Rearrangements in the Gas Phase: The Unusual Claisen Rearrangement of Deprotonated Allyl Vinyl Ether." Australian Journal of Chemistry 43, no. 9 (1990): 1479. http://dx.doi.org/10.1071/ch9901479.

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Allyl vinyl ether is reported to undergo a facile Wittig rearrangement to yield penta-1,4-dien-3-ol under base- catalysed conditions in the condensed phase. In marked contrast, the Wittig rearrangement is not a major reaction in the gas phase. Instead, initial rearrangement occurs by a Claisen process and subsequent fragmentations involve some of the most complex interconversions yet proposed for negative ions.

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12

Maryasin, Boris, Dainis Kaldre, Renan Galaverna, Immo Klose, Stefan Ruider, Martina Drescher, Hanspeter Kählig, 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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13

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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14

Uma, R., K. Rajagopalan, and S. Swaminathan. "Base catalysed rearrangement of oxycope systems." Tetrahedron 42, no. 10 (January 1986): 2757–69. http://dx.doi.org/10.1016/s0040-4020(01)90563-0.

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15

Bock, Klaus, Inge Lundt, and Christian Pedersen. "Base-catalysed rearrangement of some bromodeoxyheptonolactones." Carbohydrate Research 179 (August 1988): 87–96. http://dx.doi.org/10.1016/0008-6215(88)84112-0.

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16

Joyce, Liam M., Anthony C. Willis, Christopher J. T. Hyland, and Stephen G. Pyne. "Gold- and Silver-Catalysed Cyclisation Reactions of β-Amino Allenes." Australian Journal of Chemistry 71, no. 9 (2018): 682. http://dx.doi.org/10.1071/ch18197.

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Herein we report the formation of pyrrolines and tetrahydropyridines from the cyclisation reactions of β-amino allenes by both AuI and AgI catalysts in yields ranging from 5 to 70 %. AuI catalysts favour a 5-endo-dig cyclisation before rapid rearrangement to the 5-exo-dig product, while AgI favours a 6-endo-trig cyclisation. We also report the first known Ag2O catalysed cyclisation reaction of an allene which occurred in good yield (61 %).

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17

Brunner, Henri, Henri B. Kagan, and Georg Kreutzer. "Asymmetric catalysis. Part 153: Metal-catalysed enantioselective α-ketol rearrangement." Tetrahedron: Asymmetry 14, no. 15 (August 2003): 2177–87. http://dx.doi.org/10.1016/s0957-4166(03)00433-6.

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18

Kiely-Collins, H. J., I. Sechi, P. E. Brennan, and M. G. McLaughlin. "Mild, calcium catalysed Beckmann rearrangements." Chemical Communications 54, no. 6 (2018): 654–57. http://dx.doi.org/10.1039/c7cc09491d.

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19

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 the N(carbamoyl)-aryl bond of the N-phthalimidomethyl derivatives of both ethyl and methyl N-(2,4-dinitrophenyl)carbamate is reported.

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20

K. Banerjee, Ajoy, and Hector E. Hurtado S. "Acid catalysed novel rearrangement of bicyclic dienone." Tetrahedron 41, no. 15 (January 1985): 3029–32. http://dx.doi.org/10.1016/s0040-4020(01)96654-2.

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21

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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22

Meshram, H. M. "Clay Catalysed Facile Beckmann Rearrangement of Ketoximes." Synthetic Communications 20, no. 20 (November 1990): 3253–58. http://dx.doi.org/10.1080/00397919008051553.

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23

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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24

Sosa Carrizo, E. Daiann, and Israel Fernández. "The effect of the metal fragment on the aromaticity and synchronicity of the gold(i)-catalysed divinylcyclopropane–cycloheptadiene rearrangement." Physical Chemistry Chemical Physics 18, no. 17 (2016): 11677–82. http://dx.doi.org/10.1039/c5cp06523b.

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25

Qiu, Huang, Hadi Arman, Wenhao Hu, and Michael P. Doyle. "Intramolecular cycloaddition/rearrangement cascade from gold(iii)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines." Chemical Communications 54, no. 91 (2018): 12828–31. http://dx.doi.org/10.1039/c8cc07885h.

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26

Vig, Rakesh, Arun Sabharwal, and Jasvinder Singh. "Synthesis of (Z)-1,8- and (E)-1,8-pentadecadiene: Tumor inhibitors." Collection of Czechoslovak Chemical Communications 56, no. 10 (1991): 2199–202. http://dx.doi.org/10.1135/cccc19912199.

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27

Boughdady, NM, KR Chynoweth, and DG Hewitt. "Thermal Dehydrochlorination of Poly(vinyl chloride) Model Compounds. II. Computer Analysis of Kinetic Results." Australian Journal of Chemistry 44, no. 4 (1991): 581. http://dx.doi.org/10.1071/ch9910581.

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Computer simulation has been used to analyse the condensed-phase thermal degradation of a series of compounds with functional groups related to defects found in poly(vinyl chloride) ( pvc ). We have been able to estimate the relative significance of catalysed and non- catalysed processes and make some estimates of the significance of allylic rearrangement.

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28

Sun, Zhen, Zheng Li, and Wei-Wei Liao. "An organocatalytic hydroalkoxylation/Claisen rearrangement/Michael addition tandem sequence: divergent synthesis of multi-substituted 2,3-dihydrofurans and 2,3-dihydropyrroles from cyanohydrins." Green Chemistry 21, no. 7 (2019): 1614–18. http://dx.doi.org/10.1039/c8gc03978j.

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29

Sherratt, Allison R., Mariya Chigrinova, Craig S. McKay, Louis-Philippe B. Beaulieu, Yanouchka Rouleau, and John Paul Pezacki. "Copper-catalysed cycloaddition reactions of nitrones and alkynes for bioorthogonal labelling of living cells." RSC Adv. 4, no. 87 (2014): 46966–69. http://dx.doi.org/10.1039/c4ra07851a.

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30

Shamanth, Sadashivamurthy, Nagaraju Chaithra, Mahesha Gurukiran, Mahesha Mamatha, N. K. Lokanath, Kanchugarakoppal S. Rangappa, and Kempegowda Mantelingu. "I2-Catalyzed transformation of o-aminobenzamide to o-ureidobenzonitrile using isothiocyanates." Organic & Biomolecular Chemistry 18, no. 14 (2020): 2678–84. http://dx.doi.org/10.1039/d0ob00118j.

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31

Kurokawa, Hideki, Satoru Nakamura, Wataru Ueda, Yutaka Morikawa, Yoshihiko Moro-oka, and Tuneo Ikawa. "Solid base-catalysed rearrangement of methacrylonitrile to crotononitrile." Journal of the Chemical Society, Chemical Communications, no. 10 (1989): 658. http://dx.doi.org/10.1039/c39890000658.

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32

Martin, Robert, and Pierre Demerseman. "Lewis acids catalysed Fries rearrangement of isopropylcresol esters." Monatshefte f�r Chemie Chemical Monthly 121, no. 2-3 (1990): 227–36. http://dx.doi.org/10.1007/bf00809536.

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33

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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34

Jaunzeme, Ieva, and Aigars Jirgensons. "Ether-directed diastereoselectivity in catalysed Overman rearrangement: comparative studies of metal catalysts." Tetrahedron 64, no. 24 (June 2008): 5794–99. http://dx.doi.org/10.1016/j.tet.2008.03.099.

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35

Bos, Maxence, and Emmanuel Riguet. "Iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones followed by heteroaromatic Cope rearrangement: study of an unusual reaction sequence." Chemical Communications 53, no. 36 (2017): 4997–5000. http://dx.doi.org/10.1039/c7cc01529a.

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36

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

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37

Yang, Zhen, Yujing Guo, and Rene M. Koenigs. "Solvent-dependent, rhodium catalysed rearrangement reactions of sulfur ylides." Chemical Communications 55, no. 58 (2019): 8410–13. http://dx.doi.org/10.1039/c9cc03809d.

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38

Ren, Jie, Xinxin Yan, Xiaofan Cui, Chao Pi, Yangjie Wu, and Xiuling Cui. "Iodine-catalysed N-centered [1,2]-rearrangement of 3-aminoindazoles with anilines: efficient access to 1,2,3-benzotriazines." Green Chemistry 22, no. 1 (2020): 265–69. http://dx.doi.org/10.1039/c9gc03567b.

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A straightforward and synthetically valuable approach for the synthesis of 1,2,3-benzotriazines has been developed via iodine-catalysed N-centered [1,2]-rearrangement of 3-aminoindazoles with anilines.

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39

Bolm, Carsten, Oliver Beckmann, and Chiara Palazzi. "Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones." Canadian Journal of Chemistry 79, no. 11 (November 1, 2001): 1593–97. http://dx.doi.org/10.1139/v01-137.

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BINOL-aluminum complexes were successfully employed as mediators and catalysts in asymmetric Baeyer-Villiger rearrangements of cyclobutanones. Good enantioselectivies were achieved with only 15 mol% of the chosen chiral Lewis acid. The enantiomeric excesses obtained have never been reached before in such metal-catalyzed Baeyer-Villiger reactions.Key words: aluminum, asymmetric catalysis, lactones, oxidations, rearrangement.

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40

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 (June 1, 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 signals are in emission. The change in the enhancement of the signals during reaction shows that the nuclear polarization arises from the rearrangement, not from a preliminary equilibrium.

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41

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 (June 4, 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 acids at the correct tricarboxylate oxidation level. The unsaturated side chain was either protected with a bromide substituent during the transketalisation or introduced afterwards by a stereoretentive Ni-catalyzed Csp3–Csp2 cross-electrophile coupling.1 Introduction 2 Racemic Model Studies to the Squalestatin/Zaragozic Acid Core3 Asymmetric Model Studies to a Keto α-Diazoester3.1 Dialkyl Squarate Desymmetrisation3.2 Tartrate Alkylation3.2.1 Further Studies on Seebach’s Alkylation Chemistry 4 Failure at the Penultimate Step to DDSQ 5 Second-Generation Approach to DDSQ: A Bromide Substituent Strategy 5.1 Stereoselective Routes to E-Alkenyl Halides via β-Oxido Phosphonium Ylides 5.2 Back to DDSQ Synthesis6 An Alternative Strategy to DDSQ: By Cross-Electrophile Coupling7 Alkene Ozonolysis in the Presence of Diazo Functionality: Accessing α-Ketoester Intermediates8 Summary

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42

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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43

Chakrabarti, Kaushik, Kuheli Dutta, and Sabuj Kundu. "Synthesis of N-methylated amines from acyl azides using methanol." Organic & Biomolecular Chemistry 18, no. 30 (2020): 5891–96. http://dx.doi.org/10.1039/d0ob01303j.

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The Ru(ii) complex catalysed direct transformation of acyl azides into N-methylamines was developed for the first time using methanol via the one-pot Curtius rearrangement and borrowing hydrogen methodology.

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44

Gutmann, Alexander, Corinna Krump, Linda Bungaruang, and Bernd Nidetzky. "A two-step O- to C-glycosidic bond rearrangement using complementary glycosyltransferase activities." Chem. Commun. 50, no. 41 (2014): 5465–68. http://dx.doi.org/10.1039/c4cc00536h.

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A 2′-O- to 3′-C-glucosidic bond rearrangement on the flavonoid-like aglycon phloretin was catalysed with perfect atom economy by coupled uridine 5′-diphosphate dependent O- and C-glycosyltransferase activities.

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45

Hock, Katharina J., Lucas Mertens, Renè Hommelsheim, Robin Spitzner, and Rene M. Koenigs. "Enabling iron catalyzed Doyle–Kirmse rearrangement reactions with in situ generated diazo compounds." Chemical Communications 53, no. 49 (2017): 6577–80. http://dx.doi.org/10.1039/c7cc02801f.

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Safe rearrangement reactions of sulfides with in situ generated diazo compounds have been developed. Transient generation of, for example, diazo acetonitrile followed by iron catalysed Doyle–Kirmse reaction generates valuable building blocks for drug discovery.

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46

Brunner, Henri, Henri B. Kagan, and Georg Kreutzer. "Asymmetric catalysis. Part 137: Nickel catalysed enantioselective α-ketol rearrangement of 1-benzoylcycloalkanols." Tetrahedron: Asymmetry 12, no. 3 (March 2001): 497–99. http://dx.doi.org/10.1016/s0957-4166(01)00045-3.

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47

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 (February 1, 2011): 124–25. http://dx.doi.org/10.3184/174751911x557296.

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48

Venkateswaran, Ramanathapuram, and Debayan Sarkar. "Facile Aromatic Claisen Rearrangement Catalysed by Tin(IV) Chloride." Synlett 2008, no. 05 (February 26, 2008): 653–54. http://dx.doi.org/10.1055/s-2008-1042806.

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49

Bhattacharya, Asish K., Dharam C. Jain, Ram P. Sharma, Raja Roy, and Andrew T. McPhail. "Boron trifluoride-acetic anhydride catalysed rearrangement of dihydroarteannuin B." Tetrahedron 53, no. 44 (November 1997): 14975–90. http://dx.doi.org/10.1016/s0040-4020(97)01049-1.

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50

Xavier, N., and S. J. Arulraj. "Rearrangement of substituted aromatic acetals catalysed by γ -alumina." Tetrahedron 41, no. 14 (January 1985): 2875–78. http://dx.doi.org/10.1016/s0040-4020(01)96608-6.

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