Radical ring expansion reactions of methylenecyclopropane derivatives: A theoretical study

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 4803-4809

  Ardura, Diego ^a   Sordo, Tomás L ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BOND; METHYLENECYCLOPROPANE; PROPYL-SUBSTITUTED RADICALS; THERMODYNAMIC CONTROL;

CHEMICAL BONDS; CHEMICAL REACTIONS; DERIVATIVES; GIBBS FREE ENERGY; SOLVENTS; THERMODYNAMIC PROPERTIES;

PROPYLENE;

1 (3 BROMOBUTYL) 1 TRIMETHYLSILYL 2 METHYLENECYCLOPROPANE; 1 (3 BROMOBUTYL) 2 ETHYL 3 METHYLENECYCLOPROPANE; 1 (3 BROMOPROPYL) 1 TRIMETHYLSILYL 2 METHYLENECYCLOPROPANE; 1 (3 BROMOPROPYL) 2 ETHYL 3 METHYLENECYCLOPROPANE; CYCLOPROPANE DERIVATIVE; METHYLENECYCLOPROPANE DERIVATIVE; PROPANE; RADICAL; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COVALENT BOND; DENSITY FUNCTIONAL THEORY; DOUBLE BOND; ENERGY TRANSFER; EXPERIMENT; GIBBS ENERGY BARRIER; LYSIS; MOLECULAR MODEL; RADICAL RING EXPANSION; THEORETICAL STUDY; THERMODYNAMICS;

COMPUTER SIMULATION; CYCLIZATION; CYCLOPROPANES; FREE RADICALS; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM; THERMODYNAMICS;

EID: 33745446612     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0602625     Document Type: Article

References (25)

1. Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991.
2. Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115.
3. Destabel, C.; Kilburn, J. D. J. Chem. Soc., Chem. Commun. 1992, 596-598.
4. Destabel, C.; Kilburn, J. D.; Knight, J. Tetrahedron Lett. 1993, 34, 3151-3154.
5. See, for example: (a) Giese, B. Radicals in Organic Syntheses: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986.
6. (b) Curran, D. P. In Comprehensive Organic Sythesis; Trost, B. M., Flemming, I. M., Semmelhack, M. F., Eds.: Pergamon: Oxford, 1991; Vol. 4.
7. (c) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995.
8. (d) Fischer, H.; Radom, L. Angew. Chem., Int. Ed. 2001, 40, 1340-1371.
9. (e) Henry, D. J.; Coote, M. L.; Gomez-Balderas, R.; Radom, L. J. Am. Chem. Soc. 2004, 126 (6), 1732-1740.
10. Hammond, D. S. J. Am. Chem. Soc. 1955, 77, 334-338.
11. Baldwin, J. E.; J. Chem. Soc., Chem. Commun. 1976, 734-736.
12. Wong, M. W.; Radom, L. J. Phys. Chem. 1995, 99, 8582-8585.
13. 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; Gaussian, Inc.: Pittsburgh, PA, 1998.
14. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
15. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
16. (c) Becke, A. D. J. Chem. Phys. 1993, 98 5648-5652.
17. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
18. Hehre, W. J.; Radom, L.; Pople, J. A.; Schleyer, P. v. R. Ab Initio Molecular Orbital Theory: John Wiley & Sons Inc.: New York, 1986.
19. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
20. McQuarrie, D. A. Statistical Mechanics; Harper & Row: New York, 1976.
21. Rivail, J. L.; Rinaldi, D.; Ruiz-López, M. F. In Theoretical and Computational Model for Organic Chemistry; Formosinho, S. J., Csizmadia, I. G., Arnaut, L., Eds.: NATO ASI Ser. C: Kluwer Academic Publishers: Dordrecht, 1991; Vol. 339, pp 79-92.
22. (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
23. (b) Cammi, R.; Tomasi, J. J. Comput. Chem. 1995, 16, 1449-1458.
24. Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161-2200.
25. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.