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(g) Böhmer, V. In The Chemistry of Phenols; Rappoport, Z., Ed.; Wiley: Chichester, 2003; Chapter 19.
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(e) Bergamaschi, M.; Bigi, F.; Lanfranchi, M.; Maggi, R.; Pastorio, A.; Pellinghelli, M. A.; Peri, F.; Porta, C.; Sartori, G. Tetrahedron 1997, 53, 13037.
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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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(g) 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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(b) Simaan, S.; Agbaria, K.; Biali, S. E. J. Org. Chem. 2002, 67, 6136.
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For a review on spirodienone calixarene derivatives see
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(e) For a review on spirodienone calixarene derivatives see: Biali, S. E. Synlett 2003, 1.
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Synlett
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Biali, S.E.1
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Middel, O.; Greff, Z.; Taylor, N. J.; Verboom, W.; Reinhoudt, D. N.; Snieckus, V. J. Org. Chem. 2000, 65, 667.
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Scully, P.A.1
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22
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41649086614
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The term classical designates calixarenes possessing bridging methylene groups connecting the phenol rings as opposed to thiacalixarenes (which possess sulfur bridges) azacalixarenes (nitrogen atoms, ketocalixarenes carbonyl groups, etc
-
The term "classical" designates calixarenes possessing bridging methylene groups connecting the phenol rings as opposed to " thiacalixarenes" (which possess sulfur bridges) "azacalixarenes" (nitrogen atoms), "ketocalixarenes" (carbonyl groups), etc.
-
-
-
-
23
-
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20444457928
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Azacalix[4]arenes substituted at several nitrogen bridges have been reported. See: (a) Tsue, H.; Ishibashi, K.; Takahashi, H.; Tamura, R. Org. Lett. 2005, 7, 2165.
-
Azacalix[4]arenes substituted at several nitrogen bridges have been reported. See: (a) Tsue, H.; Ishibashi, K.; Takahashi, H.; Tamura, R. Org. Lett. 2005, 7, 2165.
-
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24
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(b) Ishibashi, K.; Tsue, H.; Tokita, S.; Matsui, K.; Takahashi, H.; Tamura, R. Org. Lett. 2006, 8, 5991.
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Ishibashi, K.1
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Matsui, K.4
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Tamura, R.6
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Klenke, B.; Näther, C.; Friedrichsen, W. Tetrahedron Lett. 1998, 39, 8967.
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Kumar, S.K.1
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Görmar, G.; Seiffarth, K.; Schultz, M.; Zimmerman, J.; Flämig, G. Makromol. Chem. 1990, 191, 81.
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Kuno, L.1
Seri, N.2
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30
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41649115302
-
-
2 axis in the twist form of cyclohexane.
-
2 axis in the twist form of cyclohexane.
-
-
-
-
31
-
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41649083633
-
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For a review on calix[4]arene systems functionalized at one or two bridges see: Simaan, S.; Biali, S. E. J. Phys. Org. Chem. 2004, 17, 752.
-
For a review on calix[4]arene systems functionalized at one or two bridges see: Simaan, S.; Biali, S. E. J. Phys. Org. Chem. 2004, 17, 752.
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32
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(a) Iwamoto, K.; Ikeda, A.; Araki, K.; Harada, T.; Shinkai, S. Tetrahedron 1993, 49, 9937.
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Iwamoto, K.1
Ikeda, A.2
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Harada, T.4
Shinkai, S.5
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33
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0001266521
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See also
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(b) See also: van Hoorn, W. P.; Briels, W. J.; van Duynhoven, J. P. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Org. Chem. 1998, 63, 1299.
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van Hoorn, W.P.1
Briels, W.J.2
van Duynhoven, J.P.M.3
van Veggel, F.C.J.M.4
Reinhoudt, D.N.5
-
34
-
-
41649100752
-
-
A preliminary X-ray structure analysis of the molecule corroborated this structural assignment
-
A preliminary X-ray structure analysis of the molecule corroborated this structural assignment.
-
-
-
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35
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0242681670
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(a) Zavada, J.; Pankova, M.; Arnold, Z. Collect. Czech. Chem. Commun. 1976, 41, 1777.
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Zavada, J.1
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Arnold, Z.3
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36
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See also
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(b) See also: Simaan, S.; Siegel, J. S.; Biali, S. E. J. Org. Chem. 2003, 68, 3699.
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J. Org. Chem
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Simaan, S.1
Siegel, J.S.2
Biali, S.E.3
-
37
-
-
41649106141
-
-
Apparently, a mixture of isomers is obtained
-
Apparently, a mixture of isomers is obtained.
-
-
-
-
38
-
-
41649119446
-
-
A single crystal of 6e was grown from acetonitrile and submitted to X-ray crystallography. Although the structure could be refined only to a relatively high R factor (18 %), the structure corroborated the assigned rccc configuration of the macrocycle. The molecule adopts a cone conformation with the substituents located at equatorial positions and an acetonitrile molecule included in the cavity.
-
A single crystal of 6e was grown from acetonitrile and submitted to X-ray crystallography. Although the structure could be refined only to a relatively high R factor (18 %), the structure corroborated the assigned rccc configuration of the macrocycle. The molecule adopts a cone conformation with the substituents located at equatorial positions and an acetonitrile molecule included in the cavity.
-
-
-
-
39
-
-
7244238073
-
-
Hofmann, M.; Hampel, N.; Kanzian, T.; Mayr, H. Angew. Chem., Int. Ed. 2004, 43, 5402. See also:
-
(a) Hofmann, M.; Hampel, N.; Kanzian, T.; Mayr, H. Angew. Chem., Int. Ed. 2004, 43, 5402. See also:
-
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40
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0037241494
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(b) Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66.
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Acc. Chem. Res
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Mayr, H.1
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1942521170
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(c) Minegishi, S.; Kobayashi, S.; Mayr, H. J. Am. Chem. Soc. 2004, 126, 5174.
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J. Am. Chem. Soc
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Minegishi, S.1
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Mayr, H.3
-
42
-
-
41649117605
-
-
It is interesting to note that, although reflux of 2b in a 1:1 TFE/EtOH mixture yields exclusively 6b, heating in a 1:1 TFE/ethylene glycol mixture affords products containing both trifluoroethoxy and 2-hydroxyethoxy groups at the bridges. The lower relative nucleophilicity of the ethylene glycol molecules (as compared to that of EtOH) may be connected to the presence of inter- and intramolecular hydrogen bonds, as well as to the larger viscosity of the mixture.
-
It is interesting to note that, although reflux of 2b in a 1:1 TFE/EtOH mixture yields exclusively 6b, heating in a 1:1 TFE/ethylene glycol mixture affords products containing both trifluoroethoxy and 2-hydroxyethoxy groups at the bridges. The lower relative nucleophilicity of the ethylene glycol molecules (as compared to that of EtOH) may be connected to the presence of inter- and intramolecular hydrogen bonds, as well as to the larger viscosity of the mixture.
-
-
-
-
43
-
-
0037162774
-
-
Simaan, S.; Agbaria, K.; Biali, S. E. J. Org. Chem. 2002, 67, 6136.
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J. Org. Chem
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-
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Simaan, S.1
Agbaria, K.2
Biali, S.E.3
-
44
-
-
41649090468
-
-
When the reaction was conducted in TFE, a different isomeric mixture was obtained, the major form corresponding to the rctt isomer.
-
When the reaction was conducted in TFE, a different isomeric mixture was obtained, the major form corresponding to the rctt isomer.
-
-
-
-
45
-
-
41649086205
-
-
The SCN carbon of ethyl thiocyanate resonates at 112 ppm, while in isothiocyanates the carbon resonance is about ca. 20 ppm shifted downfield. See: Ben-Efraim, D. A. In The Chemistry of Cyanates and their Thio Derivatives, Part 1; Patai, S., Ed., Wiley: Chichester, 1977; Chapter 5, p 227.
-
The SCN carbon of ethyl thiocyanate resonates at 112 ppm, while in isothiocyanates the carbon resonance is about ca. 20 ppm shifted downfield. See: Ben-Efraim, D. A. In The Chemistry of Cyanates and their Thio Derivatives, Part 1; Patai, S., Ed., Wiley: Chichester, 1977; Chapter 5, p 227.
-
-
-
-
46
-
-
0001466110
-
-
For selected examples of this transformation in macrocyclic rings see: a
-
For selected examples of this transformation in macrocyclic rings see: (a) Hart, H.; Takehira, Y. J. Org. Chem. 1982, 47, 4370.
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J. Org. Chem
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47
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(b) Kohnke, F. H.; Parisi, M. F.; Raymo, F. M.; O'Neil, P. A.; Williams, D. J. Tetrahedron 1984, 50, 9113.
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Kohnke, F.H.1
Parisi, M.F.2
Raymo, F.M.3
O'Neil, P.A.4
Williams, D.J.5
-
49
-
-
41649091921
-
-
Without 1,2-butylene oxide an intractable mixture of products was obtained
-
Without 1,2-butylene oxide an intractable mixture of products was obtained.
-
-
-
-
50
-
-
41649087235
-
-
The complexity of the spectrum may be due to the presence of configurational isomers of the tetraaduct that adopt different conformations
-
The complexity of the spectrum may be due to the presence of configurational isomers of the tetraaduct that adopt different conformations.
-
-
-
-
52
-
-
0026020331
-
-
Casnati, A.; Arduini, A.; Ghidini, E. W.; Pochini, A.; Ungaro, R. Tetrahedron 1991, 47, 2221.
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Casnati, A.1
Arduini, A.2
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Pochini, A.4
Ungaro, R.5
-
53
-
-
41649101318
-
-
When the reaction was conducted with 2b, a mixture of trimethoxy and dimethoxy tetraxylyl derivatives was obtained. Since we were unable to fully methylate this mixture, we performed the reaction with the de-tert-butylated derivative 2a.
-
When the reaction was conducted with 2b, a mixture of trimethoxy and dimethoxy tetraxylyl derivatives was obtained. Since we were unable to fully methylate this mixture, we performed the reaction with the de-tert-butylated derivative 2a.
-
-
-
-
54
-
-
41649098935
-
-
Preliminary experiments indicate that reaction of 1b with excess HBr (50%) in HFIP (2 h reflux) affords the monodemethylated derivative (i.e., the trimethyl ether of p-tert-butylcalix[4]arene), while in TFE the demethylation proceeds further, and a mixture of the monomethyl ether and tetrahydroxycalixarene is obtained.
-
Preliminary experiments indicate that reaction of 1b with excess HBr (50%) in HFIP (2 h reflux) affords the monodemethylated derivative (i.e., the trimethyl ether of p-tert-butylcalix[4]arene), while in TFE the demethylation proceeds further, and a mixture of the monomethyl ether and tetrahydroxycalixarene is obtained.
-
-
-
-
55
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0004323931
-
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Tripos Inc, St. Louis, MO 63144
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Alchemy 2000; Tripos Inc.: St. Louis, MO 63144, 2000.
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Alchemy 2000
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56
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41649105367
-
-
Molecular mechanics calculations of 2a have been reported by Friedrichsen and coworkers (ref 8). These calculations were conducted assuming that each of the four forms (rccc, rcct, rctt, rctc) adopts a cone conformation. However, it was not examined whether in some substitution patterns the preferred conformation is different from cone.
-
Molecular mechanics calculations of 2a have been reported by Friedrichsen and coworkers (ref 8). These calculations were conducted assuming that each of the four forms (rccc, rcct, rctt, rctc) adopts a cone conformation. However, it was not examined whether in some substitution patterns the preferred conformation is different from cone.
-
-
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57
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21244492862
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(a) Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4955.
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Harada, T.1
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59
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41649112833
-
-
For a review on the conformation and stereodynamics of calixarenes see: Thondorf, I. in ref 1f, Chapter 15.
-
(c) For a review on the conformation and stereodynamics of calixarenes see: Thondorf, I. in ref 1f, Chapter 15.
-
-
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60
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Iwamoto, K.; Ikeda, A.; Araki, K.; Harada, T.; Shinkai, S. Tetrahedron 1993, 49, 9937.
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(a) van Hoorn, W. P.; Briels, W. J.; van Duynhoven, J. P. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Org. Chem. 1998, 63, 1299.
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See also ref 3d
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(b) See also ref 3d.
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