Synthesis and Isolation of Polytrityl Cations by Utilizing Hexaphenylbenzene and Tetraphenylmethane Scaffolds

Journal of Organic Chemistry

Volumn 69, Issue 5, 2004, Pages 1524-1530

  Rathore, Rajendra ^a   Burns, Carrie L ^a   Guzei, Ilia A ^a,b  

^a Marquette University   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

POLYTRITYL CATIONS;

AROMATIC COMPOUNDS;

BENZENE DERIVATIVE; BORANE DERIVATIVE; CATION; CYCLOHEPTATRIENE; DIMETHYL SULFIDE; METHANE; POLYTRITYL DERIVATIVE; TRIETHYLSILANE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG ISOLATION; ELECTRON TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 1442301847     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035598i     Document Type: Article

References (51)

1. (a) Shchepinov, M. S.; Korshun, V. A. Chem. Soc. Rev. 2003, 32, 170.
2. (b) Plack, V.; Schmutzler, R. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144-146, 273.
3. (c) Kobayashi, S. Kagaku Kogyo 1989, 42, 245.
4. (d) Wu, J.-T. Petrochemistry 1974, 13, 19.
5. (a) Baird, M. C.; Reid, S. J. Organometallics 2002, 21, 2325.
6. (b) Rüchardt, C. Top. Curr. Chem. 1980, 88, 1 and references therein,
7. (c) House, H. O.; Trost, B. M. J. Org. Chem. 1965, 30, 1341.
8. (a) Cox, R. A. Org. React. Mech. 1991, 283.
9. (b) Corma, A.; Garcia, H. Top. Catal. 1998, 6, 127.
10. (c) Bullock, R. M.; Cheng, T.-Y. Organometallics 2002, 21, 2325 and references therein,
11. (d) Dauben, H. J., Jr.; Bertelli, D. J. J. Am. Chem. Soc. 1961, 83, 4657 and 4659.
12. (a) Fukuzumi, S.; Ohkubo, K.; Otera, J. J. Org. Chem. 2001, 66, 1450 and references therein.
13. (b) Hart, H.; Sulzberg, T.; Schwendeman, R. H.; Young, R. H. Tetrahedron Lett. 1967, 15, 1337.
14. (c) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
15. (d) Fukuzumi, S.; Kitano, T.; Ishikawa, M. J. Am. Chem. Soc. 1990, 112, 5631.
16. (a) Hou, Z.; Kaita, S.; Wakatsuki, Y. Pure Appl. Chem. 2001, 73, 291.
17. (b) Baird, M. C.; Reid, S. J. Organometallics 2002, 21, 2325.
18. (c) Williams, V. C.; Irvine, G. J.; Piers, W. E.; Li, Z.; Collins, S.; Clegg, W.; Elsegood, M. R.; Marder, T. B. Organometallics 2000, 19, 1621.
19. (d) Shafir, A.; Arnold, J. Organometallics 2003, 22, 567 and references therein.
20. (a) Reed, C. A. Acc. Chem. Res. 1998, 31, 133,
21. (b) Ivanov, S. V.; Davis, J. A.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. Inorg. Chem. 2003, 42, 4489.
22. (a) Head, N. J.; Prakash, G. K.; Bashir-Hashemi, A.; Olah, G. A. J. Am. Chem. Soc. 1995, 117, 12005.
23. (b) Heagy, M. D.; Wang, Q.; Olah, G. A.; Prakash, G. K. J. Org. Chem. 1995, 60, 7351.
24. (a) MacDonald, R. A.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383.
25. (b) Desiraju, G. R. Crystal Engineering: The design of Organic Solids; Elsevier: New York, 1989; p 54.
26. (c) Zyss, J.; Josse, D.; Ledoux, I. MCLC S&T, Sect. B: Nonlinear Opt. 1994, 7, 169.
27. (d) Allen, N. S. Polym. Degrad. Stab. 1994, 44, 357.
28. (a) Yeh, C.-H.; Lee, R.-H.; Chan, L.-H.; Lin, T.-Y.; Chen, C.-T.; Balasubramaniam, E.; Tao, Y.-T. Chem. Mater. 2001, 13, 2788.
29. (b) Zimmermann, T. J.; Freundel, O.; Gompper, R.; Muller, J. J. J. Eur. J. Org. Chem. 2000, 3305.
30. (c) Keegstra, M. A.; Feyter, S. D.; Schryver, F. C. D.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 774.
31. (d) Oldham, W. J., Jr.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1998, 120, 2987.
32. (e) Wang, S.; Oldham, W. J., Jr.; Hudock, R. A., Jr.; Bazan, G. C. J. Am. Chem. Soc. 2000,124, 5695 and references therein.
33. (f) Berresheim, A. J.; Müller, M.; Müllen, K. Chem. Rev. 1999, 99, 1747.
34. (g) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267 and references therein.
35. (a) Rathore, R.; Burns, C. L.; Deselnicu, M. I. Org. Lett. 2001, 3, 2887.
36. (b) Rathore, R.; Burns, C. L.; Abdelwahed, S. A. Org. Lett. submitted for publication.
37. (a) Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1995, 6, 1713.
38. (b) Zimmermann, T. J.; Muller, T. J. J. Synthesis 2002, 9, 1157.
39. Burns, C. L.; Rathore, R. Org. Synth. Submitted for publication.
40. (a) Lambert, J. B.; Zhang, S.; Stern, C. L.; Huffman, J. C. Science 1993, 260, 1917.
41. (b) Also see: Badejo, I. T.; Karaman, R.; Fry, J. L. J. Org. Chem. 1989, 54, 4591.
42. A precise structure of 9 could not be determined due to the disordered solvent molecules.
43. (a) Farnum, D. G. J. Am. Chem. Soc. 1964, 86, 934.
44. (b) Also see: Farnum, D. G. Adv. Phys. Org. Chem. 1975, 11, 123.
45. Shida, T. Electronic Absorption Spectra of radical Ions; Elsevier: Amsterdam, The Netherlands, 1988.
46. Conrow, K. Org. Synth. 1963, 43, 101. Also see: Conrow, K. J. Am. Chem. Soc. 1959, 81, 5461.
47. Conrow, K. Org. Synth. 1963, 43, 101. Also see: Conrow, K. J. Am. Chem. Soc. 1959, 81, 5461.
48. (a) Hill, C. L. Chem. Rev. 1998, 98, 1.
49. (b) Pope, M. T. Heteropoly and Isopoly Oxometalates; Springer-Verlag: Berlin, Germany, 1983.
50. Bushby, R.-J. Magnetism: Molecules to Materials; Wiley-VCH: New York, 2001; Vol II, p 149.
51. Grimm, M.; Kirste, B.; Kurreck, H. Angew. Chem. 1986, 98, 1095.