Electrostatic interactions between substituents as regioselectivity control elements in Diels-Alder cycloadditions. A DFT study of cycloadditions of 1-methoxy-4-trimethylsiloxy dienes with acrylonitrile

Journal of Organic Chemistry

Volumn 67, Issue 21, 2002, Pages 7179-7184

  Ujaque, Gregori ^a   Norton, Joseph E ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVITY; SUBSTITUENTS;

ADDITION REACTIONS; ELECTROSTATICS; NITROGEN COMPOUNDS; PHASE TRANSITIONS; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS;

BUTADIENE;

1 METHOXY 4 TRIMETYLSILOXYDIENE; ACRYLONITRILE; ALKADIENE; CYCLOBUTANE DERIVATIVE; FUNCTIONAL GROUP; SOLVENT; UNCLASSIFIED DRUG; XYLENE;

ARTICLE; COLOR; CONFORMATIONAL TRANSITION; CYCLOADDITION; DIELECTRIC CONSTANT; ELECTRICITY; ELECTRON TRANSPORT; GAS; PREDICTION AND FORECASTING; STEREOCHEMISTRY; THERMODYNAMICS;

ACRYLONITRILE; ALKADIENES; ELECTROSTATICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0037131142     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020441w     Document Type: Article

References (14)

1. (a) Houk, K. N. Acc. Chem. Res. 1975, 8, 361.
2. (b) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley & Sons: New York, 1976.
3. (c) Houk, K. N.: Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
4. Kahn, S. D.; Pau, C. F.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381.
5. (a) Danishefsky, S. J.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976, 98, 3028.
6. (b) Danishefsky, S. J. Acc. Chem. Res. 1981, 14, 400.
7. Hentemann, M. F.; Allen, J. G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 1937.
8. Allen, J. G.; Hentemann, M. F.; Danishefsky, S. J. J. Am. Chem. Soc. 2000, 122, 571.
9. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; Plenum Press: New York, 1990.
10. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
11. 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.
12. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439.
13. (a) McCarrick, M. A.; Wu, Y.-D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1499.
14. (b) Liu, J.; Niwayama, S.; You, Y.; Houk, K. N. J. Org. Chem. 1998, 63, 1064 and references therein.