Dienophile twisting and substituent effects influence reaction rates of intramolecular Diels-Alder cycloadditions: A DFT study

Journal of the American Chemical Society

Volumn 127, Issue 11, 2005, Pages 3688-3689

  Khuong, Kelli S ^a   Beaudry, Chris M ^a   Trauner, Dirk ^a   Houk, K N ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,4 CYCLOHEXADIENE; 5 VINYL 1,3 CYCLOHEXADIENE DERIVATIVE; ALKENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; ENERGY TRANSFER; ENTHALPY; ISOMERISM; REACTION TIME; STEREOCHEMISTRY;

CYCLOHEXANES; CYCLOHEXENES; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; VINYL COMPOUNDS;

EID: 15744381257     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050135a     Document Type: Article

References (10)

1. Ng, S. M.; Beaudry, C. M.; Trauner, D. Org. Lett. 2003, 5, 1701-1704.
2. (In T1)(ΔG1/T1) = (In T2)(ΔG2/T2)
3. Frisch, M. J. et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
4. Guner, V.; Khuong, K. S.; Leach, A. G.; Lee, P. S.; Bartberger, M. D.; Houk, K. N. J. Phys. Chem. A 2003, 107, 11445-11459.
5. (a) Belikova, N. A.; Berezkin, V. G.; Plate, A. F. Zh. Obshch. Khim. 1962, 32, 2942-2951.
6. (b) Berson, J. A.; Hamlet, Z.; Mueller, W. A. J. Am. Chem. Soc. 1962, 84, 297-304.
7. (a) Fotiadu, R.; Michel, F.; Buono, G. Tetrahedron Lett. 1990, 31, 4863-4886.
8. (b) Takeda, K.; Imaoka, I.; Yoshii, E. Tetrahedron 1994, 50, 10839-10848.
9. (c) Kobuke, Y.; Fueno, T.; Furukawa, J. J. Am. Chem. Soc. 1970, 92, 6548-6533.
10. (d) Kobuke, Y.; Sugimoto, T.; Furukawa, J.; Fueno, T. J. Am. Chem. Soc. 1972, 94, 3633-3635.