Isolation and low-temperature X-ray analysis of intramolecular triarylmethane-triarylmethylium complex: Preference for a C-H-bridged unsymmetric structure exhibiting a facile 1,5-hydride shift and charge-transfer interaction

Journal of the American Chemical Society

Volumn 127, Issue 35, 2005, Pages 12172-12173

  Kawai, Hidetoshi ^a   Takeda, Takashi ^a   Fujiwara, Kenshu ^a   Suzuki, Takanori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; METHANE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; GEOMETRY; LOW TEMPERATURE PROCEDURES; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 24644437278     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053161h     Document Type: Article

References (31)

1. (a) Kirchen, R. P.; Sorensen, T. S.; Wagstaff, K. J. Am. Chem. Soc. 1978, 100, 6761.
2. (b) McMurry, J. E.; Hodge, C. N. J. Am. Chem. Soc. 1984, 106, 6450.
3. (a) Sorensen, T. S.; Whitworth, S. M. J. Am. Chem. Soc. 1990, 112, 8135.
4. (b) McMurry, J. E.; Lectka, T. Acc. Chem. Res. 1992, 25, 47.
5. (c) Taeschler, C.; Parvez, M.; Sorensen, T. S. J. Phys. Org. Chem. 2002, 15, 36.
6. (a) Tantillo, D. J.; Hoffmann, R. J. Am. Chem. Soc. 2003, 125, 4042.
7. (b) Ponec, R.; Yuzhakov, G.; Tantillo, D. J. J. Org. Chem. 2004, 69, 2992.
8. (c) DuPré, D. B. J Phys. Chem. A 2005, 109, 622.
9. 2C units: Kawai. H.: Nagasu, T.: Takeda, T.; Fujiwara, K.; Tsuji, T.; Ohkita, M.; Nishida, J.; Suzuki, T. Tetrahedron Lett. 2004, 45, 4553.
10. (b) Gabbaï et al. have proposed the involvement of a similar cationic complex as a transient intermediate during the reduction of the correspondes dication species: Wang, H.; Gabbaï, F. P. Angew. Chem., Int. Ed. 2004, 43, 184.
11. (a) Arduengo, A. J., III; Gamper, S. F.; Tamm, M.; Calabrese, J. C.; Davidson, F.; Craig, H. A. J. Am. Chem. Soc. 1995, 117, 572.
12. (b) Akiba, K.; Yamashita, M.; Yamamoto, Y.; Nagase, S. J. Am. Chem. Soc. 1999, 121, 10644.
13. (a) Komatsu, K.; Abe, N.; Takahashi, K.; Okamoto, K. J. Org. Chem. 1979, 44, 2712.
14. (b) Tsuji, R.; Komatsu, K.; Inoue, Y.; Takeuchi, K. J. Org. Chem. 1992, 57, 636.
15. (c) Cozzi, F.; Cineuini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729.
16. (d) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683.
17. (e) Katoh, T.: Ogawa, K.; Inagaki, Y. Okazaki, R. Tetrahedron 1997, 53, 3557.
18. (f) Wolf, C.; Mei, X. J. Am. Chem. Soc. 2003, 125, 10651.
19. Kawai, H.; Takeda, T.; Fujiwara, K.; Suzuki, T. Tetrahedron Lett. 2004, 45, 8289.
20. (a) 3.076(2) A: ref 4b.
21. (b) 3.1 12(4) Å: Wang, H.; Webster, C. E.; Pérez, L. M.; Hall, M. B.; Gabbaï. F. P. J. Am. Chem. Soc. 2004, 126, 8189.
22. (c) 3.062(5) Å: Suzuki, T.; Tanaka, S.; Higuchi, H.; Kawai, H.; Fujiwara, K. Tetrahedron Lett. 2004, 45, 8563.
23. The nature of heteroatomic 3c bonds was investigated by adopting the naphthalenediyl framework: (a) Katz, H. E. J. Am. Chem. Soc. 1985, 107, 1420.
24. (b) Staab, H. A.; Saupe, T. Angew. Chem., Int. Ed. Engl. 1988, 27, 865.
25. (c) Hoefelmeyer, J. D.; Schulte, M.; Tschinkl, M.; Gabbaï. F. P. Coord. Chem. Rev. 2002, 235, 93.
26. (d) Reiter, S. A.; Nogai, S. D.; Karaghiosoff, K.; Schmidbaur, H. J. Am. Chem. Soc. 2004, 126, 15833.
27. See Supporting Information.
28. 2+ salts with hydride reagents gave two products: arylenebis(N-methylacridan) by double hydride addition and the 2e reduction product with two (spiro-N-methylacridan) units.
29. Altman, L. J.; Laungani, P.; Gunnarsson, G.; Wennerström, H.; Forsén, S. J. Am. Chem. Soc. 1978, 100, 8264.
30. Frisch, M. J. et al. Gaussian 98, revision A.7: Gaussian, Inc.: Pittsburgh. PA, 1998.
31. Studies on the localized/delocalized geometry in the organic 3c bonds have the common concerns to the organic intervalence ion radicals with the localized/delocalized structure: Nelsen, S. F.; Konradsson, A. E.; Telo, J. P. J. Am. Chem. Soc. 2005, 127, 920 and references therein.