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Journal articles on the topic 'Claisen Rearrangemant'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Zhang, Beibei, Xiaoxian Li, Boying Guo, and Yunfei Du. "Hypervalent iodine reagent-mediated reactions involving rearrangement processes." Chemical Communications 56, no. 91 (2020): 14119–36. http://dx.doi.org/10.1039/d0cc05354f.

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We summarize the developments of hypervalent iodine reagents-mediated reactions involving [1,2]-migration, Hofmann rearrangement, Beckmann rearrangement, ring contraction/expansion, [3,3]-sigmatropic/iodonium-Claisen rearrangement and some miscellaneous rearrangements.

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2

McGeary, Ross, Jed Burns, and Elizabeth Krenske. "Claisen Rearrangements of Benzyl Vinyl Ethers and Heterobenzyl Vinyl Ethers." Synthesis 50, no. 09 (2018): 1750–72. http://dx.doi.org/10.1055/s-0036-1589529.

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The Claisen rearrangement of benzylic substrates (benzyl vinyl ethers) has received considerably less attention than its well-known aliphatic and normal aromatic variants. Here, we review the rearrangement of both benzylic and heterobenzylic substrates, with examples of the reaction’s use in the synthesis of natural products and drug-like molecules.1 Introduction2 Early Attempts at the Benzyl-Claisen Rearrangement3 Successful Benzylic Examples4 Heterobenzylic Examples5 Conclusion

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3

Krištofíková, Dominika, Juraj Filo, Mária Mečiarová, and Radovan Šebesta. "Why do thioureas and squaramides slow down the Ireland–Claisen rearrangement?" Beilstein Journal of Organic Chemistry 15 (December 10, 2019): 2948–57. http://dx.doi.org/10.3762/bjoc.15.290.

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A range of chiral hydrogen-bond-donating organocatalysts was tested in the Ireland–Claisen rearrangement of silyl ketene acetals. None of these organocatalysts was able to impart any enantioselectivity on the rearrangements. Furthermore, these organocatalysts slowed down the Ireland–Claisen rearrangement in comparison to an uncatalyzed reaction. The catalyst-free reaction proceeded well in green solvents or without any solvent. DFT calculations showed that the activation barriers are higher for reactions involving hydrogen-donating organocatalysts and kinetic experiments suggest that the catal

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4

Jain, Seema. "Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines." Heterocyclic Communications 25, no. 1 (2019): 22–26. http://dx.doi.org/10.1515/hc-2019-0010.

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Abstract7-Allylindolines are valuable synthons for designing biologically active molecular libraries. Lewis acid catalyzed amino-Claisen rearrangement provides a one pot synthetic entry to these heteroarenes. In this context, Zinc chloride (ZnCl2)–N,N-dimethylformamide system efficiently catalyzed amino-Claisen rearrangements of 1-N-allylindolines to 7-allylindolines. The rearrangement is influenced by stereoelectronic effects of substituents present in 1-N-allylindolines. The substrates containing electron donating functionalities underwent rearrangement at lower temperature than substrates w

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5

Gille, Annika, Julia Rehbein, and Martin Hiersemann. "Gosteli−Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements." Organic Letters 13, no. 8 (2011): 2122–25. http://dx.doi.org/10.1021/ol200558j.

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6

Ito, Hisanaka, and Takeo Taguchi. "Asymmetric Claisen rearrangement." Chemical Society Reviews 28, no. 1 (1999): 43–50. http://dx.doi.org/10.1039/a706415b.

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7

Takano, Seiichi, Shun’ichi Tomita, Michiyasu Takahashi, and Kunio Ogasawara. "Thionolactone Claisen Rearrangement." Chemistry Letters 16, no. 7 (1987): 1379–80. http://dx.doi.org/10.1246/cl.1987.1379.

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8

Dudziński, Piotr, Wibke S. Husstedt, Andrej V. Matsnev, Joseph S. Thrasher, and Günter Haufe. "Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5607–23. http://dx.doi.org/10.1039/d1ob00870f.

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[3,3]-Sigmatropic rearrangements based on different SF<sub>5</sub>-substituted allylic alcohols were investigated. The synthetic sequence developed for SF<sub>5</sub> compounds is also useful for CF<sub>3</sub> analogues and its application in Johnson–Claisen rearrangement.

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9

Nadali, Samaneh, Ghasem Aghapour, and Zahra Rafieepour. "Efficient and selective iron-mediated reductive Claisen rearrangement of propargyloxyanthraquinones to anthrafurandiones in ionic liquids." Canadian Journal of Chemistry 95, no. 10 (2017): 1045–51. http://dx.doi.org/10.1139/cjc-2017-0328.

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An efficient and rapid method is described for the reductive Claisen rearrangement of different propargyloxyanthraquinones to anthra[1,2-b]furan-6,11-diones for first time using iron powder in a mixture of two ionic liquids, namely 1-methylimidazolium tetrafluoroborate [Hmim]BF4 and 1-benzyl-3-methylimidazolium chloride [Bzmim]Cl. The present method is able to execute single or double Claisen rearrangements of 1,4- or 1,5-bispropargyloxyanthraquinones selectively, so that the desired anthra(mono)furandiones or anthra(bis)furandiones are produced, respectively, as the major product.

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10

Gopalan, B., K. Rajagopalan, K. Sunitha, and K. K. Balasubramanian. "Studies in claisen rearrangement." Tetrahedron 41, no. 15 (1985): 3153–59. http://dx.doi.org/10.1016/s0040-4020(01)96670-0.

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11

Ito, Hisanaka, Azusa Sato, and Takeo Taguchi. "Enantioselective aromatic Claisen rearrangement." Tetrahedron Letters 38, no. 27 (1997): 4815–18. http://dx.doi.org/10.1016/s0040-4039(97)01040-x.

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12

Gonda, Jozef. "The Belluš–Claisen Rearrangement." Angewandte Chemie International Edition 43, no. 27 (2004): 3516–24. http://dx.doi.org/10.1002/anie.200301718.

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13

Gille, Annika, Julia Rehbein, and Martin Hiersemann. "ChemInform Abstract: Gosteli-Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements." ChemInform 42, no. 30 (2011): no. http://dx.doi.org/10.1002/chin.201130032.

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14

Tymoshenko, Dmytro. "Microwave-Assisted Claisen and Aza-Claisen Rearrangements." Mini-Reviews in Organic Chemistry 5, no. 2 (2008): 85–95. http://dx.doi.org/10.2174/157019308784223587.

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15

Wipf, Peter, and Sonia Rodríguez. "Water-Accelerated Claisen Rearrangements." Advanced Synthesis & Catalyis 344, no. 3-4 (2002): 434–40. http://dx.doi.org/10.1002/1615-4169(200206)344:3/4<434::aid-adsc434>3.0.co;2-#.

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16

Balasubramanian, K. K., N. G. Ramesh, Animesh Pramanik, and Jayaraman Chandrasekhar. "Aromatic Claisen rearrangements in carbohydrates: stereocontrol of rearrangement rates in unsaturated sugar substrates." Journal of the Chemical Society, Perkin Transactions 2, no. 7 (1994): 1399. http://dx.doi.org/10.1039/p29940001399.

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17

Nohira, Hiroyuki, and Toshiyuki Nohira. "Dynamic correlation diagrams for sigmatropic reactions based on orbital phase conservation theory." Journal of Theoretical and Computational Chemistry 16, no. 06 (2017): 1750055. http://dx.doi.org/10.1142/s0219633617500559.

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For sigmatropic reactions, such as [1,3] and [1,5] hydrogen shifts, the Cope and Claisen rearrangements, and the Berson–Nelson rearrangement, no correlation diagrams consistent with the classical electronic formulas have been reported. Here, we report dynamic correlation diagrams for these sigmatropic reactions based on orbital phase conservation theory. The diagrams are consistent with both the selection rules of sigmatropic reactions proposed by Woodward and Hoffmann and classical electronic formulas.

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18

Ramadhar, Timothy, Jun-ichi Kawakami, and Robert Batey. "Sequential O-Arylation/Lanthanide(III)-Catalyzed [3,3]-Sigmatropic Rearrangement of Bromo-Substituted Allylic Alcohols." Synlett 28, no. 20 (2017): 2865–70. http://dx.doi.org/10.1055/s-0036-1590890.

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Lanthanide(III)-catalyzed aryl-Claisen rearrangement of substrates bearing halo-substituted allyl groups, specifically 2-bromoallyl aryl ethers, afford ortho-2-bromoallylphenols. Aryl ether substrates were synthesized from brominated allylic alcohols via Mitsunobu reaction, Cu(II)-catalyzed arylation using potassium aryltrifluoroborate salts, or SNAr reaction. Aryl-Claisen rearrangements proceeded in moderate to excellent yields using Eu(III) catalysis. The alkenylbromide functionality remains intact, illustrating the compatibility of synthetically important alkenylhalides during C–O/C–C σ-bon

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19

Tena, Alberto, Sofia Rangou, Sergey Shishatskiy, Volkan Filiz, and Volker Abetz. "Claisen thermally rearranged (CTR) polymers." Science Advances 2, no. 7 (2016): e1501859. http://dx.doi.org/10.1126/sciadv.1501859.

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Thermally rearranged (TR) polymers, which are considered the next-generation of membrane materials because of their excellent transport properties and high thermal and chemical stability, are proven to have significant drawbacks because of the high temperature required for the rearrangement and low degree of conversion during this process. We demonstrate that using a [3,3]-sigmatropic rearrangement, the temperature required for the rearrangement of a solid glassy polymer was reduced by 200°C. Conversions of functionalized polyimide to polybenzoxazole of more than 97% were achieved. These highl

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20

Gajdošíková, Eva, Miroslava Martinková, Jozef Gonda, and Patrik Conka. "Microwave Accelerated Aza-Claisen Rearrangement." Molecules 13, no. 11 (2008): 2837–47. http://dx.doi.org/10.3390/molecules131102837.

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21

Ziegler, Frederick E. "The thermal, aliphatic Claisen rearrangement." Chemical Reviews 88, no. 8 (1988): 1423–52. http://dx.doi.org/10.1021/cr00090a001.

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22

Tellier, Frédérique, Max Audouin, Monique Baudry, and Raymond Sauvêtre. "Claisen rearrangement of allylfluorovinyl ethers." Tetrahedron Letters 39, no. 28 (1998): 5041–44. http://dx.doi.org/10.1016/s0040-4039(98)01002-8.

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23

Jain, Sanjay, Neelima Sinha, Dinesh K. Dikshit, and Nitya Anand. "Thio-Claisen rearrangement on pyroglutamates." Tetrahedron Letters 36, no. 46 (1995): 8467–68. http://dx.doi.org/10.1016/0040-4039(95)01731-v.

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24

Ishihara, Jun, Yuki Watanabe, Noriko Koyama, Yukihiro Nishino, Keisuke Takahashi, and Susumi Hatakeyama. "Indium-mediated Reformatsky–Claisen rearrangement." Tetrahedron 67, no. 20 (2011): 3659–67. http://dx.doi.org/10.1016/j.tet.2011.03.079.

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25

Jackson, D. Y., J. W. Jacobs, R. Sugasawara, S. H. Reich, P. A. Bartlett, and Peter G. Schultz. "An antibody-catalyzed Claisen rearrangement." Journal of the American Chemical Society 110, no. 14 (1988): 4841–42. http://dx.doi.org/10.1021/ja00222a060.

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26

Krafft, Marie E., Sandra Jarrett, and Olivier A. Dasse. "A ligand assisted Claisen rearrangement." Tetrahedron Letters 34, no. 51 (1993): 8209–12. http://dx.doi.org/10.1016/s0040-4039(00)61392-8.

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27

Craig, Donald, N. Paul King, Jörg T. Kley, and David M. Mountford. "Heteroaromatic Decarboxylative Claisen Rearrangement Reactions." Synthesis, no. 19 (2005): 3279–82. http://dx.doi.org/10.1055/s-2005-918448.

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28

Tellier, Frédérique, Max Audouin, Monique Baudry, and Raymond Sauvêtre. "Claisen rearrangement of allylfluorovinyl ethers." Journal of Fluorine Chemistry 94, no. 1 (1999): 27–36. http://dx.doi.org/10.1016/s0022-1139(98)00313-3.

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29

Craig, Donald, N. Paul King, and David M. Mountford. "Silyl-modified Belluš–Claisen rearrangement." Chem. Commun., no. 10 (2007): 1077–79. http://dx.doi.org/10.1039/b614535c.

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30

Majumdar, Krishna C., Safiul Alam, and Buddhadeb Chattopadhyay. "Catalysis of the Claisen rearrangement." Tetrahedron 64, no. 4 (2008): 597–643. http://dx.doi.org/10.1016/j.tet.2007.10.079.

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31

Ritter, Kurt. "Claisen rearrangement of organotin compounds." Tetrahedron Letters 31, no. 6 (1990): 869–72. http://dx.doi.org/10.1016/s0040-4039(00)94650-1.

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32

Ito, Hisanaka, and Takeo Taguchi. "ChemInform Abstract: Asymmetric Claisen Rearrangement." ChemInform 30, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199917315.

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33

Majumdar, K. C., and Trijit Bhattacharyya. "ChemInform Abstract: Aza-Claisen Rearrangement." ChemInform 33, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.200235279.

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34

Woerpel, K., and S. Calad. "Diastereoselective Silylene/Ireland-Claisen Rearrangement." Synfacts 2007, no. 5 (2007): 0519. http://dx.doi.org/10.1055/s-2007-968446.

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35

Miller, Steven P., and James P. Morken. "Catalytic Diastereoselective Reductive Claisen Rearrangement." Organic Letters 4, no. 16 (2002): 2743–45. http://dx.doi.org/10.1021/ol026273b.

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36

Nelson, S., M. Geherty, and R. Dura. "Ruthenium-Catalyzed Asymmetric Claisen Rearrangement." Synfacts 2010, no. 11 (2010): 1270. http://dx.doi.org/10.1055/s-0030-1258795.

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37

Klyuchareva, E. V., E. V. Ershova, R. G. Nigmatullina, M. Yu Vozhdaeva, and E. A. Kantor. "On the Claisen rearrangement mechanism." Doklady Chemistry 424, no. 2 (2009): 52–55. http://dx.doi.org/10.1134/s0012500809020086.

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38

Yun, Sung-Jun, Kun-Hoe Chung, and Byung-Chan Yu. "Stereoselectivity of the Ortho Ester Claisen Rearrangement of Substituted Silylpropargylic Alcohols." Journal of the Korean Chemical Society 48, no. 4 (2004): 439–42. http://dx.doi.org/10.5012/jkcs.2004.48.4.439.

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39

Majumdar, K. C., and S. K. Chattopadhyay. "Synthesis of pyrimidine annulated furothiopyrans An efficient sequential and tandem catalyzed Claisen rearrangement intramolecular hydroaryloxylation." Canadian Journal of Chemistry 84, no. 3 (2006): 469–75. http://dx.doi.org/10.1139/v06-020.

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Regioselective synthesis of a hitherto unreported furothiopyran moiety fused at the C-5 and C-6 positions of a pyrimidine heterocycle was achieved by the application of sequential Claisen rearrangement in which a second aromatic Claisen rearrangement and intramolecular hydroaryloxylation were catalyzed by aluminum chloride. The second aromatic Claisen rearrangement step was also studied under thermal conditions to give mostly isomerized exocyclic compounds. The precursor endocyclic compounds were synthesized by thermal [3,3] sigmatropic rearrangement of the corresponding sulfide.Key words: alu

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40

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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41

Gonda, Jozef, Miroslava Martinková, Andrea Zadrošová, et al. "Microwave accelerated aza-Claisen rearrangements." Tetrahedron Letters 48, no. 39 (2007): 6912–15. http://dx.doi.org/10.1016/j.tetlet.2007.07.157.

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42

Funk, Raymond L., John B. Stallman, and John A. Wos. "Claisen rearrangements of enol phosphates." Journal of the American Chemical Society 115, no. 19 (1993): 8847–48. http://dx.doi.org/10.1021/ja00072a051.

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43

Mukherjee, Ashis, Qianhong Wu, and William J. le Noble. "Face Selection in Claisen Rearrangements." Journal of Organic Chemistry 59, no. 12 (1994): 3270–74. http://dx.doi.org/10.1021/jo00091a010.

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44

ALTENBACH, H. J. "ChemInform Abstract: Diastereoselective Claisen Rearrangements." ChemInform 22, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199149320.

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45

Daub, G. William, Paula L. Shanklin, and Claudia Tata. "Stereoselective acid-catalyzed Claisen rearrangements." Journal of Organic Chemistry 51, no. 17 (1986): 3402–5. http://dx.doi.org/10.1021/jo00367a041.

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46

Gozzo, Fábio Cesar, Sergio Antonio Fernandes, Denise Cristina Rodrigues, Marcos Nogueira Eberlin, and Anita Jocelyne Marsaioli. "Regioselectivity in Aromatic Claisen Rearrangements." Journal of Organic Chemistry 68, no. 14 (2003): 5493–99. http://dx.doi.org/10.1021/jo026385g.

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47

TSUNODA, Tetsuto, and Shô ITÔ. "Aza-Claisen Rearrangement. Conception and Evolution." Journal of Synthetic Organic Chemistry, Japan 52, no. 2 (1994): 113–20. http://dx.doi.org/10.5059/yukigoseikyokaishi.52.113.

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48

Okada, Yutaka, and Daisuke Imanari. "Claisen and Intermolecular Rearrangement of Cinnamyloxynaphthalenes." International Journal of Organic Chemistry 02, no. 01 (2012): 38–43. http://dx.doi.org/10.4236/ijoc.2012.21007.

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49

Desimoni, Giovanni, Giuseppe Faita, Anna Gamba, Pier Paolo Righetti, Gianfranco Tacconi, and Lucio Toma. "Substituents effect on the claisen rearrangement." Tetrahedron 46, no. 6 (1990): 2165–78. http://dx.doi.org/10.1016/s0040-4020(01)89781-7.

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50

Vance, Robert L., Nelson G. Rondan, K. N. Houk, et al. "Transition structures for the Claisen rearrangement." Journal of the American Chemical Society 110, no. 7 (1988): 2314–15. http://dx.doi.org/10.1021/ja00215a059.

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