The Influence of Fluorine Substitution on Diels-Alder Reaction of 3-Vinylcoumarin and Ethylene

• Autorzy: Koroniak H. , Pasikowska M. , Fiedorow P.
• Języki publikacji: EN

Abstrakty

EN

Density Functional Theory (DFT) has been applied to study the concerted mechanism of the Diels-Alder reaction between 3-vinylcoumarin and ethylene, as well as their fluorinated analogues. The main goal was to establish the fluorine influence on reactivity and structure of transition state (TS) and predict the reaction path. Computations were performed at the B3LYP/6-31G* level, which allowed to optimise the structure of reactants and products.

Słowa kluczowe

EN

coumarin; Diels-Alder reaction; fluorine-substituted compounds; molecular modelling; DFT

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 11
• Strony: 1523--1528
• Opis fizyczny: Bibliogr. 14 poz., rys.

Twórcy

autor

Koroniak H.

• Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Pasikowska M.

• Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Fiedorow P.

• Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

Bibliografia

• 1. Bissell E.R., Mitchell A.R. and Smith R.E., J. Org. Chem., 45, 2283 (1980).
• 2. Work presented at the National Meeting of the ACS (’97) by C.A. Roney.
• 3. Schimitschek E.J., Trias J.A., Hammond P.R. and Atkins R.L., Optics Commun., 11, 352 (1974).
• 4. Mtihlpfordt A., Schanz R., Emsting N.P., Farztdinov V. and Grimme S., Phys. Chem. Chem. Phys., 1, 3209(1999).
• 5. Fletcher A.N., Pietrak M.E. and Bliss D.E., Appl. Phys. B, 42, 79 (1987).
• 6. Gee K.R., Haugland R.P. and Sun W„ Pat. US 5, 830, 912.
• 7. Li H.Y. and Boswell G.A., Tetrahedron Lett., 37 (10), 1551 (1996).
• 8. Minami T.,Matsumoto Y., Nakamura S., Koyanagi S.and Yamaguchi M., J. Org. Chem.,57, 167(1992).
• 9. Hudlicky M. and Pavlath A.E., Organic Fluorine Compounds II, A Critical Review, ACS Monograph, American Chemical Society, Washington, DC 1995.
• 10. Houk K.N., Acc. Chem. Res., 8, 361 (1975).
• 11. Becke A.D..J. Chem. Phys., 98, 5648 (1993).
• 12.Houk K.N., Li Y and Evanseck J.D., Angew. Chem. Int. Ed. Engl., 31, 682 (1992).
• 13. Goldstein E., Beno B. and Houk K.N., J. Am. Chem. Soc., 118, 6036 (1996). 
• 14. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski' Montgomery J.A., 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., Adam Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q, Morokuma K., Malick D.K., Rabuck/ Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Pis P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M. A., Peng C.J., Nanayal A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B.G., Chen W., Wong M.W., Andres Head-Gordon M., Replogle E.S. and Pople J.A., Gaussian 98 (Revision A. 1), Gaussian, Inc., Pittsburg PA, 1998.