Computational discovery of a novel automerization process for 1-fluorocyclopropene

Organic Letters

Volumn 4, Issue 2, 2002, Pages 233-235

  Dolbier Jr , William R ^a   Robert Shelton, G ^a   Battiste, Merle A ^a   Stanton, John F ^b   Price, David R ^b  

^a University of Florida   (United States)

^b University of Texas at Austin   (United States)

Author keywords

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ARTICLE;

EID: 0037545680     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0169574     Document Type: Article

References (28)

1. Getty, S. J.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 1521-1527.
2. Dolbier, W. R., Jr. Acc. Chem. Res. 1981, 14, 195-200.
3. Tian, F.; Lewis, S. B.; Bartberger, M. D.; Dolbier, W. R.; Borden, W. T. J. Am. Chem. Soc. 1998, 120, 6187-6188.
4. Abdo, B. T.; Alberts, I. L.; Attfield, C. J.; Banks, R. E.; Blake, A. J.; Brain, P. T.; Cox, A. P.; Puham, C. R.; Rankin, D. W. H.; Robertson, H. E.; Murtagh, V.; Heppeler, A.; Morrison, C. J. Am. Chem. Soc. 1996, 118, 209-216.
5. Baird, M. S.; Spencer, K.; Krasnoshchiokov, S. V.; Panchenko, Y. N.; Stepanov, N. F.; De Mare, G. R. J. Phys. Chem. A 1998, 102, 2363-2371.
6. Xidos, J. D.; Gosse, T. L.; Burke, E. D.; Poirier, R. A.; Burnell, D. J. J. Am. Chem. Soc. 2001, 123, 5482-5488.
7. Wiberg, K. B.; Marquez, M. J. Am. Chem. Soc. 1998, 120, 2932-2938.
8. 13 Calculated rate constants were derived from transition-state theory.
9. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
10. Becke, A. D. J. Chem. Phys. 1993, 95, 5648-5652.
11. Hariharan, P. C.; Pople, J. A. Theor. Chem. Acta 1973, 28, 213-222.
12. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
13. Raghavachari, K.; Trucks, G. W. J. Chem. Phys. 1989, 91, 1062-1065.
14. Srinivasan, R. J. Am. Chem. Soc. 1969, 91, 6250-6253.
15. Bailey, I. M.; Walsh, R. J. Chem. Soc., Faraday Trans, 1 1978, 74, 1146.
16. Karni, M.; Oref, I.; Barzilai-Gilboa, S.; Lifshitz, A. J. Phys. Chem. 1988, 92, 6924-6929.
17. York, E. J.; Dittmar, W.; Stevenson, J. R.; Bergman, R. G. J. Am. Chem. Soc. 1973, 95, 5680-5687.
18. Yoshimine, M.; Pacansky, J.; Honjou, N. J. Am. Chem. Soc. 1989, 111, 2785-2798.
19. Yoshimine, M.; Pacansky, J.; Honjou, N. J. Am. Chem. Soc. 1989, 111, 4198-4209.
20. Likhotvorik, I. R.; Brown, D. W.; Jones, M., Jr. J. Am. Chem. Soc. 1994, 116, 6175-6178.
21. Hopf, H.; von der Schulenburg, W. G.; Walsh, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 381-383.
22. Note that the 17.7 kcal/mol difference between an α-fluoro- and a β-fluorocarbene that was estimated in eq 2 provides a value for the energy of the putative carbene intermediate from distal bond cleavage (31.4 kcal/ mol) that is quite close, but higher than the computed ΔE‡ value of 29.7 kcal/mol.
23. 28
24. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479-483.
25. The basis is fully described in the following: Szalay, P. G.; Stanton, J. F.; Bartlett, R. J. Chem. Phys. Lett. 1992, 193, 573.
26. Head, J. D.; Zerner, M. C. Adv. Quantum Chem. 1988, 20, 241.
27. Sclick, T. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publisher: New York, 1992; Vol. 3, pp 1-71.
28. Gauss, J.; Stanton, J. F. Chem. Phys. Lett. 1997, 276, 70-77.