Synthesis and Properties of Azoles and Their Derivatives. Part LV*. Mechanism of c,C,N-Triphenylnitrone [2+3]-Cycloaddition with (E)-3,3,3-Trichloro-1-nitropropene-1 in the Light of AM1 and AM1/COSMO Calculations

• Autorzy: Jasiński R. , Brandel E. , Barański A.
• Języki publikacji: EN

Abstrakty

EN

AM1 calculations suggest that the [2+3]-cycloaddition of C,C,N-triphenylnitrone (1) to (E)-3,3,3-trichloro-1-nitropropene-1 (2) in gas phase occurs in concerted manner. Kinetic factors favour the formation of cycloadduct with nitrogen group in position C4 of the isoxazolidine ring (path A). Introduction of toluene as a dielectric medium does not alter this preferable. However, the character of the energy profile for path A undergoes a critical change. In this case, two transition states and intermediate with zwitterionic character were localized by means of AM1/COSMO method.

Słowa kluczowe

EN

[2+3] cycloaddition; AM1 calculation; nitrone; nitroalkene; isoxazolidine

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 1
• Strony: 83--88
• Opis fizyczny: Bibliogr. 17 poz., rys.

Twórcy

autor

Jasiński R.

• Institute of Organic Chemistry and Technology, Technical University, ul. Warszawska 24, 31-155 Cracov, Poland

autor

Brandel E.

• Institute of Organic Chemistry and Technology, Technical University, ul. Warszawska 24, 31-155 Cracov, Poland

autor

Barański A.

• Institute of Organic Chemistry and Technology, Technical University, ul. Warszawska 24, 31-155 Cracov, Poland

Bibliografia

• 1. Jasiński R., Ciężkowska A., Lubimcev A. and Barański A., Izv. VUZ (Khim. & Khim. Tekhnol), (2003), in press.
• 2. Barański A., Jasiński R. and Żurowski K., J. Phys. Org. Chem., 16, 279 (2003).
• 3. Barański A., J. Mol. Struct. (TheoChem), 499, 185 (2000).
• 4. Huisgen R., Mlostoń G. and Langhals E., J. Am. Chem. Soc., 108, 6401 (1986).
• 5. Huisgen R., Mlostoń G. and Langhals E., J. Org. Chem., 51,4085 (1986).
• 6. Mlostoń G., Huisgen R. and Giera H., Tetrahedron, 58, 4185 (2002).
• 7. Huisgen R., Mlostoń G., Giera H. and Langhals E., Tetrahedron, 58, 507 (2002).
• 8. Huisgen R., Langhals E., Mlostoń G. and Oshima T., Heterocycles, 29, 2069 (1999).
• 9. Huisgen R., Langhals E. and Oshima T., Heterocycles, 29, 2075 (1999).
• 10. Huisgen R., Mlostoń G. and Langhals E., Helv. Chim. Acta., 84, 1805 (2001).
• 11. Black D.St.C. and Crozier R.F.I.D., A ust J. Chem., 31, 2239 (1978).
• 12. Houk K.N., Acc. Chem. Res., 8, 361 (1975).
• 13. Dewar M.J., Zoebisch E.G., Haely E.F. and Steward J.J.P., J. Am. Chem. Soc., 107, 3902 (1985).
• 14. Barański A., Olszańska M. and Barańska K., J. Phys. Org. Chem., 13, 489 (2000).
• 15. Jasiński R., Ciężkowska A. and Barański A., Chem. Het. Comp. (2003), in press.
• 16. Barański A., Jasiński R. and Bujak M., Polish J. Chem., 76, 145 (2002).
• 17. Leroy G., Sana M., Burke L.A. and Nguyen M.T., Quantum Theory Chem. React., 1, 91