Superelectrophiles and the effects of trifluoromethvl substituents

Journal of the American Chemical Society

Volumn 132, Issue 10, 2010, Pages 3266-3267

  O'Connor, Matthew J ^a   Boblak, Kenneth N ^a   Topinka, Michael J ^a   Kindelin, Patrick J ^a   Briski, Jason M ^a   Zheng, Chong ^a   Klumpp, Douglas A ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATIONIC SITES; CHARGE DELOCALIZATION; ELECTRONWITHDRAWING; ELECTROPHILIC CHARACTER; SUPERACID; SUPERELECTROPHILES; TRIFLUOROMETHYL; TRIFLUOROMETHYL GROUP;

ACIDS; GRAFTING (CHEMICAL);

SYNTHESIS (CHEMICAL);

ALCOHOL; ELECTROPHILE; HETEROCYCLIC COMPOUND; METHYL GROUP; DRUG DERIVATIVE; MESYLIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; TRIFLUOROACETIC ACID; TRIFLUOROMETHANESULFONIC ACID;

ALKYLATION; ARTICLE; CHEMICAL REACTION KINETICS; HEATING; IONIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PROTON TRANSPORT; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; CHEMISTRY; SYNTHESIS;

MESYLATES; PYRIDINES; TRIFLUOROACETIC ACID;

EID: 77950515423     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1001482     Document Type: Article

References (20)

1. (a) Olah, G. A.; Chambers, R. D.; Prakash, G. K. S. Synthetic Fluorine Chemistry; Wiley: New York, 1992.
2. (b) Schlosser, M. Angew. Chem., Int. Ed. 1998, 37, 1496.
3. (c) Olah, G. A.; Prakash, G. K S.; Molnar, A.; Sommer, J. Superacid Chemistry, 2nd ed.; Wiley: New York, 2009.
4. Klumpp, D. A. ACS Symp. Ser. 2007, 395, 144.
5. Olah, G. A.; Klumpp, D. A. Superelectrophiles and Their Chemistry; Wiley: New York, 2008.
6. Klumpp, D. A.; Garza, G.; Sanchez, G. V.; Lau, S.; DeLeon, S. J. Org. Chem. 2000, 65, 8997.
7. Prakash, G. K. S.; Panja, C.; Shakhmin, A.; Shah, E.; Mathew, T.; Olah, G. A. J. Org. Chem. 2009, 74, 8659, and references cited therein.
8. (a) Allen, A. D.; Kanagasabapathy, V. M.; Tidwell, T. T. J. Am. Chem. Soc. 1986, 108, 3470.
9. (b) Allen, A. D.; Fujio, M.; Mohammed, N.; Tidwell, T. T.; Tsuji, Y. J. Org. Chem. 1997, 62, 246.
10. (c) Creary, X. Chem. Rev. 1991, 91, 1625.
11. (d) Begue, J.-P.; Benayoud, F.; Bonnet-Delpon, D.; Allen, A. D.; Cox, R. A.; Tidwell, T. T. Gazz- Chim. Ital. 1995, 125, 399.
12. (a) Olah, G. A.; Prakash, G. K S.; Shih, J. G.; Krishnamurthy, V. V.; Mateescu, G. D.; Liang, G.; Sipos, G.; Buss, V.; Gund, T. M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1985, 107, 2764.
13. (b) Prakash, G. K. S.; Krishnamurthy, V. V.; Arvanaghi, M.; Olah, G. A. J. Org. Chem. 1985, 50, 3985.
14. (c) Olah, G. A.; Comisarow, M. B. J. Am. Chem. Soc. 1966, 88, 3313.
15. For somewhat related examples of biphenyl group formation, see: (a) Ohwada, T.; Okabe, K.; Ohta, T.; Shudo, K. Tetrahedron 1990, 46, 7539.
16. (b) Shudo, K.; Ohta, T.; Ohwada, T. J. Am. Chem. Soc. 1981, 103, 645.
17. (c) Nakamura, S.; Sugimoto, H.; Ohwada, T. J. Am. Chem. Soc. 2007, 129, 1724.
18. The exact role of dicationic superelectrophiles in the condensation of 25a has not been determined, but by analogy to other diketones (see pp 140142 of ref 3), the reaction may be initiated by protonation of both carbonyl groups. The final cyclization step occurs via the monocationic electrophile 27. Substrates 11 and 12 react via distonic superelectrophiles.
19. (a) Cakir, S. P.; Stokes, S.; Sygula, A.; Mead, K. T. J. Org. Chem. 2009, 74, 7529.
20. (b) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.