M-1,3,6,8,10b,10c-hexamethyl-10b,10c-dihydropyrene-2,7-dione: The use of a tether to control the stereochemistry

European Journal of Organic Chemistry

Volumn , Issue 2, 2002, Pages 243-249

  Bodwell, Graham J ^a   Bridson, John N ^a   Chen, Shu Ling ^a   Li, Jiang ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

Bowl shaped molecules; Cyclophanes; Quinones; Small ring systems

Indexed keywords

PYRIDINE;

AM1 CALCULATIONS; BOWL-SHAPED MOLECULE; BOWL-SHAPED STRUCTURES; CRYSTAL STRUCTURE DETERMINATION; CYCLOPHANES; HEATS OF FORMATION; SMALL RING SYSTEMS; TITLE COMPOUNDS; TRIMETHYLPHENOL; X RAY CRYSTAL STRUCTURES;

CRYSTAL STRUCTURE;

1,3,6,8,10B,10C HEXAMETHYL 10B,10C DIHYDROPYRENE 2,7 DIONE; CYCLOPHANE DERIVATIVE; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0036156040     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(20021)2002:2<243::AID-EJOC243>3.0.CO;2-6     Document Type: Article

References (27)

1. R. H. Mitchell in Advances in Theoretically Interesting Molecules (Ed.: R. P. Thummel), JAI Press, London, 1989; Vol. 1, pp 135-199.
2. R. H. Mitchell, Eur. J. Org. Chem. 1999, 2695-2703.
3. R. H. Mitchell, T. K. Vinod, G. J. Bodwell, K. S. Weerawarna, W. Anker, R. V. Williams, G. W. Bushnell, Pure Appl. Chem. 1986, 58, 15-24.
4. R. V. Williams, W. D. Edwards, A. Vij, R. W. Tolbert, R. H. Mitchell, J. Org. Chem. 1998, 65, 3125-3127.
5. R. H. Mitchell, V. Boekelheide, J. Am. Cliem. Soc. 1970, 92, 3510-3512.
6. R. H. Mitchell, Hctcrocyclcs 1978, 11, 563-568.
7. G. J. Bodwell, J. N. Bridson, S.-L. Chen, J. Am. Cliem. Soc. 2001, 123, 4704-4708.
8. G. J. Bodwell, T. J. Houghton, J. W. J. Kennedy, M. R. Mannion, Angcn: Client. 1996, 108, 2280-2281; Angew. Cliem. Int. Ed. Engl. 1996,55,2121-2123.
9. G. J. Bodwell, T. J. Houghton, H. E. Koury, B. Yarlagadda, Synktt 1995,751-752.
10. The complexity of the NMR spectra of this compound indicates that it adopts a time averaged conformation that has neither a twofold axis nor a plane of symmetry.
11. 1H NMR spectrum is very complex. The structural assignment is by analogy to a higher homologue, for which an X-ray crystal structure has been determined: G. J. Bodwell, J. N. Bridson, S.-L. Chen , unpublished results.
12. V. Boekelheide, J. B. Phillips, J. Am. Cliem. Soc. 1967, 89, 1695-1704.
13. J. B. Phillips, R. J. Molyneux, E. Sturm, V. Boekelheide, J. Am. Clicm. Soc. 1967, 59, 1704-1709.
14. V. Boekelheide, T. Miyasaka, J. Am. Cliem. Soc. 1967, 89, 1709-1714.
15. H. B. Renfroe, J. A. Gurney, L. A. R. Hall, J. Org. Clicm. 1972, 37, 3045-3052.
16. An irreversible oxidation was also observed at +1.8 V.
17. A. J. Bard, L. R. Faulkner, Electrochemical Methods. Fundamentals and Applications; John Wiley and Sons: New York, 1980.
18. G. J. Bodwell, J. N. Bridson, T. J. Houghton, J. W. J. Ken-nedy, M. R. Mannion, Chan. Eur. J. 1999, 5, 1823-1827.
19. G. J. Bodwell, J. N. Bridson, T. J. Houghton, J. W. J. Kennedy, M. R. Mannion, Angeu: Cliem. 1996,108, 1418-1420; Angew. Client. Int. Ed. Engl. 1996, 35, 1320-1321.
20. G. J. Bodwell, J. J. Flemine, M. R. Mannion, D. O. Miller, J. Org. Client. 2000, 65, 5360-5370.
21. For crystal structural data for 1,4-benzoquinone see [14a] J. Trotter, Acta Crystallogr. 1960, 13, 86-95. For general bond length data see:
22. M. B. Smith, J. E. March, Advanced Organic Chemistry. Reactions, Mechanism, and Structure, Wiley Interscience, New York, 2001, p. 20.
23. 1H NMR spectroscopy see: [I5a] M. Nakamura, M. Oki, H. Nakanishi, J. Am. Client. Soc. 1973, 95, 7169-7171.
24. M Nakamura, M. Oki, H. Nakanishi, O. Yamamoto, Bull. Chem. Soc. Jpn. 1974, 47, 2415-2419.
25. G. J. Bodwell, J. J. Flemina, D. O. Miller, Tetrahedron 2001, 57, 3577-3585.
26. 1H NMR spectra of tmns-19 and trtins-2l were recorded on continuous wave instruments operating at 60 MHz. It is very likely that the analyte concentrations were considerably higher than those used in this work. Any arguments about the meaning of the magnitude and direction of these small chemical shift differences would be very difficult to defend.
27. teXsan for Windows version 1.06: Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, TX (1997-9). teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, TX (1985 & 1992).