Conversion of a [6]helicene into an [8]helicene and a helical 1,10- phenanthroline ligand

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 302-305

  Fox, Joseph M ^a   Katz, Thomas J ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; LIGAND; ORGANIC COMPOUND; PHENANTHROLINE DERIVATIVE; PHENYLENEDIAMINE DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033534571     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9817570     Document Type: Article

References (45)

1. 2a The majority of helicene syntheses that do not use light have produced examples that racemize at a significant rate at room temperature (see ref 3, footnotes 1-3 and 6).
2. (a) Mallory, F. B.; Mallory, C. W. Organic Reactions; Wiley: New York, 1984; Vol. 30, p 1.
3. (b) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63.
4. (c) Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769.
5. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054.
6. See footnote 8 in ref 3, and Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031.
7. Liu, L.; Katz, T. J. Tetrahedron Lett. 1990, 31, 3983.
8. Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767.
9. Fox, J. M.; Goldberg, N. R.; Katz T. J. J. Org. Chem. 1998, 63, 7456.
10. (a) Martin, R. H.; Flammang-Barbieux, M.; Cosyn, J. P.; Gelbcke, M. Tetrahedron Lett. 1968, 3507.
11. (b) Martin, R. H.; Libert, V. J. Chem. Res. Synop. 1980, 130, and ref 1 therein.
12. (c) Moradpour, A.; Kagan, H.; Baes, M.; Morren, G.; Martin, R. H. Tetrahedron 1975, 31, 2139, and ref 12 therein.
13. Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1891, 113, 8993.
14. Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895.
15. Yang, B. V. Ph.D. Dissertation, Columbia University, 1987.
16. Willmore, N. D. Ph.D. Dissertation, Columbia University, 1994.
17. Dai, Y.; Katz, T. J. J. Org, Chem. 1997, 62, 1274.
18. (a) Ott, R. Monatsh. Chem. 1959, 90, 827.
19. (b) Ott, R.; Lachnit, R. Monatsh. Chem. 1973, 104, 15.
20. 16
21. (a) Ružička, E.; Bekárek, V.; Kandrnál, J. Collect. Czech. Chem. Commun. 1975, 40, 1738.
22. (b) Corbett, J. F. Spectrochim. Acta 1964, 20, 1665.
23. (c) Badger, G. M.; Pearce, R. S.; Pettit, R. J. Chem. Soc. 1951, 3204.
24. (d) Albert, A.; Short, L. N. J. Chem. Soc. 1945, 760.
25. 16a
26. -1 that 10 does not.
27. 1H FT NMR Spectra; Pouchert, C. J., Behnke, J., Eds.; Aldrich Chemical Co.: Milwaukee, WI, 1993.
28. 12
29. Barton, D. H. R.; Finet, J.-P.; Thomas, M. Tetrahedron 1988, 44, 6397.
30. Berger, S.; Rieker, A. In The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; Wiley: London, 1974; Chapter 4.
31. Mason, A. T. J. Chem. Soc. 1889, 55, 97.
32. For metal complexes of 4,7-diaza-1,10-phenanthroline, see: (a) Karlsson, K.; Moucheron, C.; Kirsch-De Mesmaeker, A. New J. Chem. 1994, 18, 721, and ref 15 therein.
33. (b) Real, J. A.; Muñoz, M. C.; Andrés, E.; Granier, T.; Gallois, B. Inorg. Chem. 1994, 33, 3587.
34. (c) Didler, P.; Ortmans, I.; Kirsch-De Mesmaeker, A.; Watts, R. J. Inorg. Chem. 1993, 32, 5239, and refs 4 and 19 therein.
35. (d) Didler, P.; Jacquet, L.; Kirsch-De Mesmaeker, A.; Hueber, R.; van Dorsselaer, A. Inorg. Chem. 1992, 31, 4803, and refs 9a and 15 therein.
36. (e) Vogler, C.; Schwederski, B.; Klein, A.; Kaim, W. J. Organomet. Chem. 1992, 436, 367.
37. (f) Masschelein, A.; Kirsch-De Mesmaeker, A.; Willsher, C. J.; Wilkinson, F. J. Chem. Soc., Faraday Trans. 1991, 87, 259, and ref 19 therein.
38. Wrighton, M.; Morse, D. L. J. Am. Chem. Soc. 1974, 96, 998.
39. Pallenberg, A. J.; Koenig, K. S.; Barnhart, D. M. Inorg. Chem. 1995, 34, 2833.
40. 28b
41. (a) Canty, A. J.; Skelton, B. W.; Traill, P. R.; White, A. H. Aust. J. Chem. 1992, 45, 417.
42. (b) Newkome, G. R.; Fronczek, F. R.; Gupta, V. K.; Puckett, W. E.; Pantaleo, D. C.; Kiefer, G. E. J. Am. Chem. Soc. 1982, 104, 1782.
43. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
44. 3CN, 544 nm when it is benzene, and 527 nm when it is THF. The spectra are displayed in the Supporting Information.
45. M + 2 peaks are frequently observed in the mass spectra of o-quinones. Thus, the observed peak in the mass spectrum of 9 corresponds to (M + 2) + 1. See Zeller, K.-P. In The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; Wiley: London, 1974; Chapter 5.