메뉴 건너뛰기




Volumn 73, Issue 18, 2008, Pages 7327-7335

Functionalization of the methylene bridges of the calix[6]arene scaffold

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CHEMICAL REACTIONS;

EID: 52449090783     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801187z     Document Type: Article
Times cited : (33)

References (63)
  • 1
    • 0003433022 scopus 로고
    • For reviews on calixarenes see: a, Vicens, J, Böhmer, V, Eds, Kluwer: Dordrecht
    • For reviews on calixarenes see: (a) Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991.
    • (1991) Calixarenes, a Versatile Class of Macrocyclic Compounds
  • 5
    • 0004268367 scopus 로고    scopus 로고
    • Royal Society of Chemistry: Cambridge
    • (e) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
    • (1998) Calixarenes Revisited
    • Gutsche, C.D.1
  • 6
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens, J, Eds, Kluwer: Dordrecht
    • (f) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer: Dordrecht, 2001.
    • (2001) Calixarenes 2001
  • 7
    • 0345736841 scopus 로고    scopus 로고
    • Rappoport, Z, Ed, Wiley: Chichester, Chapter 19
    • (g) Böhmer, V. In The Chemistry of Phenols; Rappoport, Z., Ed.; Wiley: Chichester, 2003; Chapter 19.
    • (2003) The Chemistry of Phenols
    • Böhmer, V.1
  • 8
    • 33846154921 scopus 로고    scopus 로고
    • 4]metacyclophanes substituted at the nitrogen bridges see: (a) Ishibashi, K.; Tsue, H.; Tokita, S.; Matsui, K.; Takahashi, H.; Tamura, R. Org. Lett. 2006, 8, 5991.
    • 4]metacyclophanes substituted at the nitrogen bridges see: (a) Ishibashi, K.; Tsue, H.; Tokita, S.; Matsui, K.; Takahashi, H.; Tamura, R. Org. Lett. 2006, 8, 5991.
  • 19
    • 33748822682 scopus 로고    scopus 로고
    • For a review on the synthesis of calixarenes via the stepwise and fragment condensation methods see: (g) Böhmer, V. Liebigs Ann./Recueil 1997, 2019
    • For a review on the synthesis of calixarenes via the stepwise and fragment condensation methods see: (g) Böhmer, V. Liebigs Ann./Recueil 1997, 2019.
  • 24
    • 0037244554 scopus 로고    scopus 로고
    • For a review on spirodienone calixarene derivatives, see: e
    • For a review on spirodienone calixarene derivatives, see: (e) Biali, S. E. Synlett 2003, 1.
    • (2003) Synlett , pp. 1
    • Biali, S.E.1
  • 27
    • 52449135426 scopus 로고    scopus 로고
    • For a review on the stereochemistry of calix[4]arene derivatives functionalized at one or two bridges, see: Simaan, S.; Biali, S. E. J. Phys. Org. Chem. 2004, 17, 752.
    • For a review on the stereochemistry of calix[4]arene derivatives functionalized at one or two bridges, see: Simaan, S.; Biali, S. E. J. Phys. Org. Chem. 2004, 17, 752.
  • 30
    • 34347271003 scopus 로고    scopus 로고
    • A calix[6]arene possessing a single carbonyl bridge was synthesized by Sone and co-workers by a stepwise route
    • (b) Kogan, K.; Biali, S. E. Org. Lett. 2007, 9, 2393. A calix[6]arene possessing a single carbonyl bridge was synthesized by Sone and co-workers by a stepwise route.
    • (2007) Org. Lett , vol.9 , pp. 2393
    • Kogan, K.1    Biali, S.E.2
  • 37
    • 52449129202 scopus 로고    scopus 로고
    • A higher proportion of TFE yielded products (according to NMR spectroscopy) containing bridges substituted by both 2-hydroxyethoxy and trifluoroethoxy groups.
    • A higher proportion of TFE yielded products (according to NMR spectroscopy) containing bridges substituted by both 2-hydroxyethoxy and trifluoroethoxy groups.
  • 38
    • 52449103169 scopus 로고    scopus 로고
    • Unfortunately, the structure could only be refined to a relatively high R factor (R = 0.1339).
    • Unfortunately, the structure could only be refined to a relatively high R factor (R = 0.1339).
  • 39
    • 52449085697 scopus 로고    scopus 로고
    • As a result of broadening effects, no coupling is observed for the signals of the diastereotopic methylene and the methyl moieties of the ethoxy groups
    • As a result of broadening effects, no coupling is observed for the signals of the diastereotopic methylene and the methyl moieties of the ethoxy groups.
  • 41
    • 52449087941 scopus 로고    scopus 로고
    • 6 and the OH group of the HFIP molecules. For the ca. 20:1 mixture used, the labeling of the OH groups of both the ethanol and HFIP molecules should be about 5%. If the source of the hydrogen transferred is the hydroxyl group of either the ethanol or HFIP molecules (a mechanism not involving hydride transfer), disregarding solvent isotope effects, it could be expected that only a small percent of deuterium should be incorporated at the bridges.
    • 6 and the OH group of the HFIP molecules. For the ca. 20:1 mixture used, the labeling of the OH groups of both the ethanol and HFIP molecules should be about 5%. If the source of the hydrogen transferred is the hydroxyl group of either the ethanol or HFIP molecules (a mechanism not involving hydride transfer), disregarding solvent isotope effects, it could be expected that only a small percent of deuterium should be incorporated at the bridges.
  • 44
    • 18244371903 scopus 로고    scopus 로고
    • For an example of the utilization of the 1,3-dipolar cycloaddition of azides for the preparation of water soluble calixarenes, see
    • For an example of the utilization of the 1,3-dipolar cycloaddition of azides for the preparation of water soluble calixarenes, see: Ryu, E.-H.; Zhao, Y. Org. Lett. 2005, 7, 1035.
    • (2005) Org. Lett , vol.7 , pp. 1035
    • Ryu, E.-H.1    Zhao, Y.2
  • 45
    • 18844402891 scopus 로고    scopus 로고
    • For a calix[4]arene substituted at two bridges by dimethylamino groups, see: Simaan, S.; Biali, S. E. Org. Lett. 2005, 7, 1817.
    • For a calix[4]arene substituted at two bridges by dimethylamino groups, see: Simaan, S.; Biali, S. E. Org. Lett. 2005, 7, 1817.
  • 46
    • 52449094894 scopus 로고    scopus 로고
    • The minor product formed is probably a pentaazido mono(trifluoroethoxy) calix[6]arene derivative as evidenced by the small quartet at ca. 3.95 ppm characteristic of the protons of a trifluoroethoxy group
    • The minor product formed is probably a pentaazido mono(trifluoroethoxy) calix[6]arene derivative as evidenced by the small quartet at ca. 3.95 ppm characteristic of the protons of a trifluoroethoxy group.
  • 48
    • 52449087645 scopus 로고    scopus 로고
    • 2 all of the lower rim methoxy groups are oriented in an out fashion (i.e., pointing away from the cavity) and/or the twist angles of the rings is different.
    • 2 all of the lower rim methoxy groups are oriented in an "out" fashion (i.e., pointing away from the cavity) and/or the twist angles of the rings is different.
  • 49
    • 52449088217 scopus 로고    scopus 로고
    • 5 and that the macrocycle adopts a pinched cone conformation. Unfortunately, the structure could only be refined to a relatively high R factor, but we believe the major structural features mentioned above are trustworthy.
    • 5 and that the macrocycle adopts a "pinched cone" conformation. Unfortunately, the structure could only be refined to a relatively high R factor, but we believe the major structural features mentioned above are trustworthy.
  • 50
    • 52449125515 scopus 로고    scopus 로고
    • We thank Dr. Roy Hoffman (Hebrew University) for conducting this experiment
    • We thank Dr. Roy Hoffman (Hebrew University) for conducting this experiment.
  • 51
    • 0002198613 scopus 로고    scopus 로고
    • For other approaches based on derivatizing the OH groups of a calix[6]arene with bulky groups or via bridging, see: (a) Grynszpan, F.; Aleksiuk, O.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1993, 13.
    • For other approaches based on derivatizing the OH groups of a calix[6]arene with bulky groups or via bridging, see: (a) Grynszpan, F.; Aleksiuk, O.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1993, 13.
  • 62
    • 52449103730 scopus 로고    scopus 로고
    • This reaction was also attempted with the tetrabromocalixarene 1b, but reaction in either TFE or HFIP afforded only a complex mixture
    • This reaction was also attempted with the tetrabromocalixarene 1b, but reaction in either TFE or HFIP afforded only a complex mixture.
  • 63
    • 52449122514 scopus 로고    scopus 로고
    • 13C NMR spectrum.
    • 13C NMR spectrum.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.