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Volumn 10, Issue 7, 2008, Pages 1393-1396

Oxyfunctionalization of calixarene quinone rings

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EID: 59849087064     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800090u     Document Type: Article
Times cited : (13)

References (51)
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    • For general reviews on calixarenes, see: a
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    • (1995) Angew. Chem., Int. Ed. Engl , vol.34 , pp. 713
    • Böhmer, V.1
  • 3
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    • Royal Society of Chemistry: Cambridge
    • (c) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
    • (1998) Calixarenes Revisited
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  • 4
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens J, Eds, Kluwer: Dordrecht
    • (d) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001.
    • (2001) Calixarenes 2001
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    • Rappoport, Z, Ed, Wiley: Chichester, U.K, Chapter 19
    • (e) Böhmer, V. In The Chemistry of Phenols; Rappoport, Z., Ed.; Wiley: Chichester, U.K., 2003; Chapter 19.
    • (2003) The Chemistry of Phenols
    • Böhmer, V.1
  • 6
    • 84892021501 scopus 로고    scopus 로고
    • Vicens J, Harrowfield, J, Eds, Springer, Dordrecht
    • (f) Calixarenes in the Nanoworld; Vicens J., Harrowfield, J., Eds.; Springer, Dordrecht, 2007.
    • (2007) Calixarenes in the Nanoworld
  • 7
    • 59849085604 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 8
    • 34247528591 scopus 로고    scopus 로고
    • For the functionalization of methylene bridge via ketocalixarenes, see: b
    • For the functionalization of methylene bridge via ketocalixarenes, see: (b) Kuno, L.; Seri, N.; Biali, S. E. Org. Lett. 2007, 9, 1577.
    • (2007) Org. Lett , vol.9 , pp. 1577
    • Kuno, L.1    Seri, N.2    Biali, S.E.3
  • 9
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    • For the functionalization of methylene bridge via spirodienone calixarene derivatives, see: c
    • For the functionalization of methylene bridge via spirodienone calixarene derivatives, see: (c) Agbaria, K.; Biali, S. E. J. Am. Chem. Soc. 2001, 123, 12495.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 12495
    • Agbaria, K.1    Biali, S.E.2
  • 12
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    • For a review on the oxidation and reduction of calixarene aromatic rings see: a, Asfari, Z, Böhmer, V, Harrowfield, J, Vicens J, Eds, Kluwer: Dordrecht, Chapter 14, pp
    • For a review on the oxidation and reduction of calixarene aromatic rings see: (a) Biali, S. E. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens J., Eds.; Kluwer: Dordrecht, 2001; Chapter 14, pp 266-279.
    • (2001) Calixarenes 2001 , pp. 266-279
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  • 13
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    • and references therein. For examples relative to hydrogenation to cyclohexane-based calixarene derivatives, see: b
    • 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.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 11806
    • Columbus, I.1    Haj-Zaroubi, M.2    Biali, S.E.3
  • 15
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    • For examples relative to oxidation of calixarene phenol rings to quinone or dienone systems, see: d
    • For examples relative to oxidation of calixarene phenol rings to quinone or dienone systems, see: (d) Morita, Y.; Agawa, T.; Kai, Y.; Kanehisa, N.; Kasai, N.; Nomura, E., Taniguchi, H. Chem. Lett. 1989, 1349.
    • (1989) Chem. Lett , pp. 1349
    • Morita, Y.1    Agawa, T.2    Kai, Y.3    Kanehisa, N.4    Kasai, N.5    Nomura, E.6    Taniguchi, H.7
  • 17
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    • 1349 Reddy, P. A, Kashyap, R. P, Watson, W. H, Gutsche, C. D. Isr. J. Chem. 1992, 32, 89
    • (f) 1349 Reddy, P. A.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. Isr. J. Chem. 1992, 32, 89.
  • 31
    • 33751386348 scopus 로고    scopus 로고
    • For examples of syntheses using calixquinones derivatives as starting material, see: (a) Reddy, P. A, Gutsche, C. D. J. Org. Chem 1993, 58, 3245
    • For examples of syntheses using calixquinones derivatives as starting material, see: (a) Reddy, P. A.; Gutsche, C. D. J. Org. Chem 1993, 58, 3245.
  • 36
    • 33746019914 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 37
    • 59849098889 scopus 로고    scopus 로고
    • See the Supporting Information for additional details
    • See the Supporting Information for additional details.
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    • Royal Society of Chemistry: Cambridge
    • (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989; pp 110-111.
    • (1989) Calixarenes , 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.
    • 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.
  • 45
    • 59849110476 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 46
    • 59849103930 scopus 로고    scopus 로고
    • 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
    • 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.
  • 49
    • 59849096663 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 51
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    • N2 attack led to an oxetane ring forming an unusual 6-oxabicyclo[3:1:1]heptane system.
    • N2 attack led to an oxetane ring forming an unusual 6-oxabicyclo[3:1:1]heptane system.


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