The reactive nature of α-ammonium distonic radical cations

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 7041-7044

  Rios, Luz Amalia ^a,b   Bartberger, Michael D ^a   Dolbier Jr , William R ^a   Paredes, Rodrigo ^b  

^a University of Florida ^*  (United States)

^b UNIVERSIDAD DEL VALLE   (Colombia)

Author keywords

[No Author keywords available]

Indexed keywords

QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030866022     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01707-3     Document Type: Article

References (11)

1. Rios, L. A.; Dolbier, W. R., Jr.; Paredes, R.; Lusztyk, J.; Ingold, K. U.; Jonsson, M. J. Am. Chem. Soc. 1996, 118, 11313-11314.
2. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
3. Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062-3072.
4. Gauld, J. W.; Radom, L. J. Phys. Chem. 1994, 98, 777-784.
5. a) Bordwell, F. G.; Cheng, J.-P.; Seyedrezai, S. E.; Wilson, C. A. J. Am. Chem. Soc. 1988, 110, 8178-8183;
6. b) Bordwell, F. G.; Lynch, T.-Y. J. Am. Chem. Soc. 1989, 111, 7558-7562.
7. ∧2> values were approximately 0.76, indicating only very minor spin contamination. An approximation to the [QCISD(T)/6-311G**] theoretical model, denoted as [QCISD(T)/6-311G**]′ is described by E[QCISD(T)/6-311G**]′= E[QCISD(T)/6-311G**] = E[QCISD(T)/6-31G*] + E(MP2/6-311G**) - E(MP2/6-31G*) where the effect of basis set extension is partially taken into account by evaluation at the MP2 level of theory.
8. Gaussian 94 (Revision C.3), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, , C. Y.; Ayala, P. A.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; and Pople, J. A., Gaussian, Inc., Pittsburgh PA, 1995.
9. Lias, S. G.; Bartmess, J.E.; Liebman, J. F.; Holmes, J. L.; Levin, R.D.; Mallard, W. G. J. Phys. Chem. Ref. Data, Suppl. 1988, 17.
10. Radical precursors, 3a-e, were mixtures of E and Z isomers. Control studies indicated no significant kinetic impact resulting from this; indeed NMR examination of reactions terminated after 50% completion indicated that unreacted 3 had been completely isomerized to the E isomer under the reaction conditions.
11. 13C NMR, HRMS, and elemental analyses.