Combined computational and experimental studies of the mechanism and scope of the retro-Nazarov reaction

Journal of the American Chemical Society

Volumn 126, Issue 35, 2004, Pages 10954-10957

  Harmata, Michael ^a   Schreiner, Peter R ^b   Lee, Dong Reyoul ^a   Kirchhoefer, Patrick L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON DONERS; OXYALLYLIC CATION; RETRO-NAZOROV REACTIONS;

ACCELERATION; CARBON; ELECTRONS; POSITIVE IONS; PROBABILITY DENSITY FUNCTION; SYNTHESIS (CHEMICAL);

REACTION KINETICS;

ALKYL GROUP; CARBON; CYCLOPENTENE DERIVATIVE; CYCLOPENTENYL OXYALLYLIC CATION; METHYL GROUP; NATURAL PRODUCT; TURMERONE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONJUGATION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; RETRO NAZAROV REACTION; SYNTHESIS;

EID: 4444315884     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048942h     Document Type: Article

References (9)

1. Harmata, M.; Lee, D. R. J. Am. Chem. Soc. 2002, 124, 14328-14329.
2. 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 x.x; Gaussian, Inc.: Pittsburgh, PA, 1998.
3. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
4. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. The Lee-Yang-Parr nonlocal correlation functional:
5. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
6. Kallel, E. A.; Houk, K. N. J. Org. Chem. 1989, 54, 6006.
7. Paquette, L. A.; Tae, J.; Arrington, M. P.; Sadoun, A. H. J. Am. Chem. Soc. 2000, 122, 2742.
8. Motoyoshiya, J.; Miyajima, M.; Hirakawa, K.; Kakurai, T. J. Org. Chem. 1985, 50, 1326.
9. When this reaction was conducted in trifluoroethanol in triethylamine, 38 and the corresponding Michael adduct were produced in a 1:1 ratio (crude NMR) in a combined yield of 60%.