Phenylethynyl- and phenylethenylmetacyclophanes with π,π interactions

European Journal of Organic Chemistry

Volumn , Issue 4, 1999, Pages 791-795

  Cao, Derong ^a,b   Schollmeyer, Dieter ^a   Meier, Herbert ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Cesium effect; Cyclisations; Cyclophanes; Sulfur heterocycles; * transitions

Indexed keywords

METACYCLOPHANE DERIVATIVE; STILBENE;

ARTICLE; CHEMICAL BOND; CHROMATOPHORE; CIS TRANS ISOMERISM; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0032866294     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199904)1999:4<791::aid-ejoc791>3.0.co;2-b     Document Type: Article

References (20)

1. F. Vögtle, Cyclophan-Chemie, Teubner, Stuttgart, 1990.
2. F. N. Diederich, Cyclophanes, The Royal Society of Chemistry, London, 1991.
3. F. Vögtle (Ed.), Top. Curr. Chem. 1983, vol. 113 and 115.
4. Y. Dai, H. Kolshorn, H. Meier, Chem. Ber. 1994, 127, 1533-1535.
5. V. V. Kane, W. H. De Wolf, F. Bickelhaupt, Tetrahedron 1994, 50, 4575-4622.
6. M. Ramming, R. Gleiter, J. Org. Chem. 1997, 62, 5821-5829.
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8. D. Cao, H. Kolshorn, H. Meier, Tetrahedron Lett. 1996, 37, 4487-4490.
9. A. Ostrowicki, E. Koepp, F. Vögtle, Top. Curr. Chem. 1992, 161, 37-67; see also H. Meier, Y. Dai, Tetrahedron Letters 1993, 34, 5277-5280.
10. A. Ostrowicki, E. Koepp, F. Vögtle, Top. Curr. Chem. 1992, 161, 37-67; see also H. Meier, Y. Dai, Tetrahedron Letters 1993, 34, 5277-5280.
11. M. Sindler-Kulyk, W. H. Laarhoven, J. Am. Chem. Soc. 1978, 100, 3819-3830.
12. U. Burkert, N. L. Allinger, Molecular Mechanics, Am. Chem. Soc., Washington D. C., 1982.
13. See H. Meier, Angew. Chem. 1992, 104, 1425-1446; Angew. Chem. Int. Ed. Engl. 1992, 31, 1399-1420 and references therein.
14. See H. Meier, Angew. Chem. 1992, 104, 1425-1446; Angew. Chem. Int. Ed. Engl. 1992, 31, 1399-1420 and references therein.
15. The nomenclature of the cyclophanes described here corresponds to the nomenclature of bicycles and not to the special phane nomenclature.[14]
16. IUPAC (Ed.: E. W. Godley) Phane Nomenclature, New Malden, Surrey, U.K., 1993.
17. Additional couplings to the olefinic protons.
18. An additional long-range coupling takes place across the triple bond.
19. INDOR and NOE measurements reveal that the signal at higher field belongs to the proton in α-position to the phenyl substituent.
20. Crystallographic data for 15 can be obtained on request from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, Germany, on quotation of the deposition number CSD-410325, the authors' names, and the full journal citation.