Synthesis and Reactivity of a 1,8-Bis(methylium)naphthalenediyl Dication

Angewandte Chemie - International Edition

Volumn 43, Issue 2, 2003, Pages 184-187

  Wang, Huadong ^a   Gabbaï, François P ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Arenes; Carbocations; Cooperative effects; Electrochemistry; Lewis acids

Indexed keywords

ELECTRONS; MOLECULAR DYNAMICS; REDUCTION; SYNTHESIS (CHEMICAL);

ELECTRON AFFINITY;

NAPHTHALENE;

1,8 BIS(METHYLIUM)NAPTHALENEDIYL DICATION; CATION; LEWIS ACID; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTROCHEMISTRY; ELECTRON; REDUCTION; SYNTHESIS;

EID: 0345862327     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353011     Document Type: Article

References (38)

1. H. H. Freedman in Carbonium Ions, Vol. IV (Eds.: G. A. Olah, P. von R. Schleyer), Wiley-Interscience, New York, 1973, chap. 28.
2. C. Herse, D. Bas, F. C. Krebs, T Bürgi, J. Weber, T. Wesolowski, B. W. Laursen, J. Lacour, Angew. Chem. 2003, 115, 3270-3274; Angew. Chem. Int. Ed. Engl. 2003, 42, 3162-3166.
3. C. Herse, D. Bas, F. C. Krebs, T Bürgi, J. Weber, T. Wesolowski, B. W. Laursen, J. Lacour, Angew. Chem. 2003, 115, 3270-3274; Angew. Chem. Int. Ed. Engl. 2003, 42, 3162-3166.
4. D. F. Duxbury, Chem. Rev. 1993, 93, 381-433.
5. For examples, see: a) E. Y.-X. Chen, T. J. Marks, Chem. Rev. 2000, 100, 1391-1434;
6. b) W. E. Piers, G. J. Irvine, V. C. Williams, Eur. J. Inorg. Chem. 2000, 2131-2142.
7. J. Nishida, T. Suzuki, T. Tsuji, J. Syn. Org. Chem. Jpn. 2002, 60, 40-51, and references therein.
8. a) T. Suzuki, J. Nishida, T. Tsuji, Angew. Chem. 1997, 109, 1387-1389; Angew. Chem. Int. Ed. Engl. 1997, 36, 1329-1331;
9. a) T. Suzuki, J. Nishida, T. Tsuji, Angew. Chem. 1997, 109, 1387-1389; Angew. Chem. Int. Ed. Engl. 1997, 36, 1329-1331;
10. b) T. Suzuki, J. Nishida, T. Tsuji, Chem. Commun. 1998, 2193-2194.
11. a) J. Nishida, T. Suzuki, M. Ohkita, T. Tsuji, Angew. Chem. 2001, 113, 3351-3354; Angew. Chem. Int. Ed. 2001, 40, 3251-3254;
12. a) J. Nishida, T. Suzuki, M. Ohkita, T. Tsuji, Angew. Chem. 2001, 113, 3351-3354; Angew. Chem. Int. Ed. 2001, 40, 3251-3254;
13. b) H. Higuchi, E. Ohta, H. Kawai, K. Fujiwara, T. Tsuji, T. Suzuki, J. Org. Chem. 2003, 68, 6605-6610.
14. W. Neugebauer, T. Clark, P. von R. Schleyer, Chem. Ber. 1983, 116, 3283-3292.
15. E. M. Arentt, R. A. Flowers II, R. T. Ludwig, A. E. Meekhof, S. A. Walek, J. Phys. Org. Chem. 1997, 10, 499.
16. 2 using the SHELXTL/PC package (version 5.1) allowed location of the remaining nonhydrogen atoms. CCDC-220813 and 220814 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrie-ving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
17. Computational details have been assembled in the Supporting Information.
18. a) J. D. Hoefelmeyer, F. P. Gabbaï, J. Am. Chem. Soc. 2000, 122, 9054-9055;
19. b) J. D. Hoefelmeyer, M. Schulte, M. Tschinkl, F. P. Gabbaï, Coord. Chem. Rev. 2002, 235, 93-103.
20. +, these potentials can be calculated at -0.28 and 1.01 V by substraction of 0.46 V (see: N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877-910.
21. T.-Y. Cheng, R. M. Bullock, J. Am. Chem. Soc. 1999, 121, 3150-3155.
22. a) H. E. Katz, J. Am. Chem. Soc. 1985, 107, 1420-1421;
23. b) F. P. Gabbaï, Angew. Chem. 2003, 115, 2318-2321; Angew. Chem. Int. Ed. 2003, 42, 2218-2221.
24. b) F. P. Gabbaï, Angew. Chem. 2003, 115, 2318-2321; Angew. Chem. Int. Ed. 2003, 42, 2218-2221.
25. J. E. McMurry, T. Lectka, Acc. Chem. Res. 1992, 25, 47-53.
26. a) K. K. Baldridge, Y. Kasahara, K. Ogawa, J. S. Siegel, K. Tanaka, F. Toda, J. Am. Chem. Soc. 1998, 120, 6167-6168, and references therein;
27. b) H. F. Bettinger, P. von R. Schleyer, H. F. Schaefer, Chem. Commun. 1998, 769-770;
28. c) K. Toda, Tanaka, M. Watanabe, K. Tamura, I. Miyahara, T. Nakai, K. Hirotsu, J. Org. Chem. 1999, 64, 3102;
29. d) B. Kahr, D. V. Engen, K. Mislow, J. Am. Chem. Soc. 1986, 108, 8305;
30. e) T. Suzuki, K. Ono, H. Kawai, T. Tsuji J. Chem. Soc. Perkin Trans. 2 2001, 1798-1801.
31. 2-. See a) J. J. Novoa, P. Lafuente, R. E. Del Sesto, J. S. Miller, Angew. Chem. 2001, 113, 2608-2613; Angew. Chem. Int. Ed. 2001, 40, 2540-2545;
32. 2-. See a) J. J. Novoa, P. Lafuente, R. E. Del Sesto, J. S. Miller, Angew. Chem. 2001, 113, 2608-2613; Angew. Chem. Int. Ed. 2001, 40, 2540-2545;
33. b) J.-M. Lü, S. V. Rosokha, J. K. Kochi, J. Am. Chem. Soc. 2003, 125, 12161-12171.
34. a) R. K. Thauer, A. R. Klein, G. C. Hartmann, Chem. Rev. 1996, 96, 3031-3042;
35. b) S. Sankararaman, W. Lau, J. K. Kochi, J. Chem. Soc. Chem. Commun. 1991, 396-398;
36. c) K. Komatsu, H. Akamatsu, S. Aonuma, Y. Jinbu, N. Maekawa, K. Takeuchi, Tetrahedron 1991, 47, 6951-6966.
37. This reaction bears some analogy with the acid-induced formation of a monocationic ketocarbenium species. See: T. Suzuki, T. Nagasu, H. Kawai, K. Fujiwara, T. Tsuji, Tetrahedron Lett. 2003, 44, 6095-6098.
38. G. A. Olah, G. K. S. Prakash, J. Sommer, Superacids, Wiley-Interscience, New York, 1985.