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For a review on the synthesis of calixarenes via the stepwise and fragment condensation methods see
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(e) For a review on the synthesis of calixarenes via the stepwise and fragment condensation methods see: Böhmer, V. Liebigs Ann./Recl. 1997, 2019.
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Homologous anionic ortho Fries rearrangement
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Homologous anionic ortho Fries rearrangement: Middel, O.; Greff, Z.; Taylor, N. J.; Verboom, W.; Reinhoudt, D. N.; Snieckus, V. J. Org. Chem. 2000, 65, 667.
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Lithiation/alkylation: Scully, P. A.; Hamilton, T. M.; Bennett, J. L. Org. Lett. 2001, 3, 2741.
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Oxidation of the methylene bridges: (a) Görmar, G.; Seiffarth, K.; Schultz, M.; Zimmerman, J.; Flämig, G. Macromol. Chem. 1990, 191, 81.
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(b) Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550.
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(c) Seri, N.; Simaan, S.; Botoshansky, M.; Kaftory, M.; Biali, S. E. J. Org. Chem. 2003, 68, 7140.
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Bromination of the methylene bridges: (a)
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Bromination of the methylene bridges: (a) Klenke, B.; Näther, C.; Friedrichsen, W. Tetrahedron Lett. 1998, 39, 8967.
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(b) Kumar, S. K.; Chawla, H. M.; Varadarajan, R. Tetrahedron Lett. 2002, 43, 7073.
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For examples of silver-mediated substitutions in bromodienone calix-arene derivatives see
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For examples of silver-mediated substitutions in bromodienone calix-arene derivatives see: Troisi, F.; Pierro, T.; Gaeta, C.; Neri, P. Org. Lett. 2009, 11, 697.
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70249094891
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note
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The configuration of the stereocenters is designated by describing the cis (c) or trans (t) disposition of the substituents relative to the reference (r) substituent. For example, a calix[5]arene derivative possessing all bridges monofunctionalized, in which all substituents are in a cis disposition relative to the reference substituent is designated as rc4.
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27
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70249134493
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note
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The reaction with MeOH or EtOH displayed poor stereoselectivity affording a complex stereoisomeric mixture.
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Hofmann, M.; Hampel, N.; Kanzian, T.; Mayr, H. Angew. Chem., Int. Ed. 2004, 43, 5402.
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(a) Bisaro, F.; Prestat, G.; Vitale, M.; Poli, G. Synlett 2002, 1823.
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(b) Jana, U.; Biswas, S.; Maiti, S. Tetrahedron Lett. 2007, 48, 4065.
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(c) Sanz, R.; Miguel, D.; Martinez, A.; Alvarez-Gutierrez, J. M.; Rodriguez, F. Org. Lett. 2007, 9, 727.
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