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Volumn 8, Issue 14, 2002, Pages 3148-3156

Calix[6]pyrrole and hybrid calix[n]furan[m]pyrroles (n + m = 6): Syntheses and host - Guest chemistry

Author keywords

Anions; Calixarenes; N ligands; Structure elucidation

Indexed keywords

BROMINE COMPOUNDS; CHLORINE COMPOUNDS; HALOGEN COMPOUNDS; PHASE TRANSITIONS; PHOSPHATES; SYNTHESIS (CHEMICAL); TITRATION;

EID: 0037101654     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20020715)8:14<3148::AID-CHEM3148>3.0.CO;2-B     Document Type: Article
Times cited : (80)

References (72)
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    • Some preliminary results obtained in the course of this study have been reported in two previous communications: a) G. Cafeo, F. H. Kohnke, G. L. La Torre, A. J. P. White, D. J. Williams, Angew Chem. 2000, 112, 1556-1558; Angew. Chem. Int. Ed. 2000, 39, 1496-1498; b) G. Cafeo, F. H. Kohnke, G. L. La Torre, A. J. P. White, D. J. Williams, Chem. Commun. 2000, 1207-1208.
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    • Some preliminary results obtained in the course of this study have been reported in two previous communications: a) G. Cafeo, F. H. Kohnke, G. L. La Torre, A. J. P. White, D. J. Williams, Angew Chem. 2000, 112, 1556-1558; Angew. Chem. Int. Ed. 2000, 39, 1496-1498; b) G. Cafeo, F. H. Kohnke, G. L. La Torre, A. J. P. White, D. J. Williams, Chem. Commun. 2000, 1207-1208.
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    • Recently an alternative approach to the synthesis of some large "hybrid" calix[n]furan[m]pyrrole has been reported: a) Y. S. Jang, H. J. Kim, P. H. Lee, C. H. Lee, Tetrahedron Lett. 2000, 41, 2919-2923; b) N. Arumugam, Y. S. Jang, C. H. Lee. Org. Lett. 2000, 2, 3115-3117.
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    • Recently an alternative approach to the synthesis of some large "hybrid" calix[n]furan[m]pyrrole has been reported: a) Y. S. Jang, H. J. Kim, P. H. Lee, C. H. Lee, Tetrahedron Lett. 2000, 41, 2919-2923; b) N. Arumugam, Y. S. Jang, C. H. Lee. Org. Lett. 2000, 2, 3115-3117.
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    • note
    • The x-ray crystal structure of the dodecaketone 5 has been determined and it will be included as part of a forthcoming paper on the use of this compound as a precursor of novel heterocyclophanes.
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    • For a review on the use of NMR methods in the evaluation of association constants see: a) L. Fielding, Tetrahedron 2000, 56, 6151-6170; b) R. S. Macomber, J. Educ. Chem. 1992, 69, 375-378, and references therein.
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    • We thank Professor M. J. Hynes for providing us with the updated version of EQNMR for Windows®
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    • note
    • Calix[6]pyrrole 2, calix[3]furan[3]pyrrole 12, calix[2]furan[4]pyrrole 13, and calix[1]furan[5]pyrrole 14, are all insoluble in water.
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    • note
    • This lack of ability of meso-dodecamethylcalix[6]pyrrole 2 to bind iodide suggests that the significant complexing ability of the 1,1,3,3,5,5-meso-hexaphenyl-2,2,4,4,6,6-meso-hexamethylcalix[6]pyr-role described by Eichen (see reft [10b]) towards this anion is essentially due to the presence of the phenyl groups.
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    • This unusual coupling between the NH protons in the host and the fluoride guest has been previously observed: a) at low temperatures for calix[4]pyrrole 1 (ref. [3c]); and b) in meso-aryl substituted calix[4]pyrroles: S. Camiolo, P. A. Gale, Chem. Commun. 2000. 1129-1130.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.