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For a procedure for the functionalization of all methylene groups via tetrabromocalix[4]arene derivatives, see: (a) Columbus, I.; Biali, S. E. Org. Lett. 2007, 32, 3201.
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For the functionalization of methylene bridge via ketocalixarenes, see: b
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and references therein. For examples relative to hydrogenation to cyclohexane-based calixarene derivatives, see: b
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For examples relative to hydrogenation to cyclohexane-based calixarene derivatives, see: (b) Columbus, I.; Haj-Zaroubi, M.; Biali, S. E. J. Am. Chem. Soc. 1998, 120, 11806 and references therein.
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For examples relative to oxidation of calixarene phenol rings to quinone or dienone systems, see: d
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For examples of syntheses using calixquinones derivatives as starting material, see: (a) Reddy, P. A.; Gutsche, C. D. J. Org. Chem 1993, 58, 3245.
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Tripropoxycalix[4]monoquinone 1 was synthesized according to a literature procedure: Lu, L.-G.; Li, G.-K.; Peng, X.-X.; Chen, C.-F.; Huang, Z.-T. Tetrahedron Lett. 2006, 47, 6021.
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Tripropoxycalix[4]monoquinone 1 was synthesized according to a literature procedure: Lu, L.-G.; Li, G.-K.; Peng, X.-X.; Chen, C.-F.; Huang, Z.-T. Tetrahedron Lett. 2006, 47, 6021.
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See the Supporting Information for additional details
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See the Supporting Information for additional details.
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0004146786
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(a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989; pp 110-111.
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Molecular modeling was performed with MacroModel-9.0/Maestro-4.1 program: Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp,R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
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Molecular modeling was performed with MacroModel-9.0/Maestro-4.1 program: Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp,R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
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45
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For another example of stable monohemiketal calix[4]arene derivative, see: Timmerman, P.; Harkema, S.; van Hummel, G. J.; Verboom, W.; Reinhoudt, D. N. J. Inclusion Phenom. Macrocyclic Chem. 1993, 16, 189.
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For another example of stable monohemiketal calix[4]arene derivative, see: Timmerman, P.; Harkema, S.; van Hummel, G. J.; Verboom, W.; Reinhoudt, D. N. J. Inclusion Phenom. Macrocyclic Chem. 1993, 16, 189.
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46
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Analogously, Lin and coworkers (see ref 7b) reported that when a calix[4]monoquinone derivative was protected with ethylene glycol only the carbonyl group at the upper rim was masked with a ketal functionality whereas the carbonyl group at the lower rim was left unreacted because of steric hindrance
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Analogously, Lin and coworkers (see ref 7b) reported that when a calix[4]monoquinone derivative was protected with ethylene glycol only the carbonyl group at the upper rim was masked with a ketal functionality whereas the carbonyl group at the lower rim was left unreacted because of steric hindrance.
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In accordance with the IUPAC cyclitol nomenclature, the diepoxy-cyclohexanediol moieties in 3, 4, and 7 can be defined as dianhydroinositol rings (J. Biol. Chem. 1968, 22, 5809). In fact, for the IUPAC rules, 1,2,3,4,5,6-cyclohexanehexols are termed generically as 'inositols', which are a class of the cyclitol (cycloalkanes containing one hydroxyl group on each of three or more ring atoms) family.
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In accordance with the IUPAC cyclitol nomenclature, the diepoxy-cyclohexanediol moieties in 3, 4, and 7 can be defined as dianhydroinositol rings (J. Biol. Chem. 1968, 22, 5809). In fact, for the IUPAC rules, 1,2,3,4,5,6-cyclohexanehexols are termed generically as 'inositols', which are a class of the cyclitol (cycloalkanes containing one hydroxyl group on each of three or more ring atoms) family.
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N2 attack led to an oxetane ring forming an unusual 6-oxabicyclo[3:1:1]heptane system.
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N2 attack led to an oxetane ring forming an unusual 6-oxabicyclo[3:1:1]heptane system.
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