Rate constants are determined for methyl iodide quaternisations of a series of 2-substituted quinolines and pyridines. Relative rates are interpreted in terms of steric effects, electronic effects and calculated geometries.
References
1.
Part 20: MarkgrafJ.H., CortJ. R., DavisH. A., LindemanN. I., MyersC. R., ChristlM., and KraftA., J. Org. Chem., 1991, 56, 3755.
DuffinG.F., Adv. Heterocycl. Chem., 1964, 3, 1; J.A. Zoltewicz and L.W. Deady, Adv. Heterocycl. Chem., 1978, 22, 71; R. Gallo, C. Roussel and U. Berg, Adv. Heterocycl. Chem., 1988, 43, 173.
4.
CoppensG., DeclerckF., GilletC., and NasielskiJ., Bull. Soc. Chim. Belges, 1963, 72, 25; J.A. Zoltewicz and L.W. Deady, J. Am. Chem. Soc., 1972, 94, 2765; L.W. Deady, Aust. J. Chem., 1973, 26, 1949; Y. Kondo, S. Izawa and S. Kusabayashi, J. Chem. Soc., Perkin Trans. 2, 1988, 1925.
5.
DeadyL.W., and ZoltewiczJ. A., J. Org. Chem., 1972, 37, 603.
6.
SeemanJ.I., GalzeranoR., CurtisK., SchugJ. C., and ViersJ. W., J. Am. Chem. Soc., 1981, 103, 5982; J.I. Seeman, J.W. Viers, J.C. Schug and M.D. Stovall, J. Am. Chem. Soc., 1984, 106, 143; J. I. Seeman, Pure Appl. Chem., 1987, 57, 1661.
7.
ArnettE.M., and ReichR. R., J. Am. Chem. Soc., 1978, 100, 2930; E.M. Arnett and R.R. Reich, J. Am. Chem. Soc., 1980, 102, 5892; C.D. Johnson, I. Roberts and P.G. Taylor, J. Chem. Soc., Perkin Trans. 2, 1981, 409.
8.
MarkgrafJ.H., and ScottW. L., J. Chem. Soc., Chem. Commun., 1967, 296; J.H. Markgraf, H.A. Davis, P.S. Ernst, K.S. Hirsch, K.J. Leonard, M.E. Morrison and C.R. Myers, Tetrahedron, 1991, 47, 183.
9.
SchugJ.C., and ViersJ. W., Tetrahedron, 1984, 40, 3971.
10.
RousselC., BalabanA. T., BergU., ChanonM., GalloR., KlatteG., MemiagheJ. A., MetzgerJ., OniciuD., and Pierrot-SandersJ., Tetrahedron, 1983, 39, 4209.
11.
The program PC MODEL was obtained from Serena Software, Bloomington, IN.
12.
DeroskiB.R., MarkgrafJ. H., and RicciJ. S.Jr.., J. Heterocycl. Chem., 1983, 20, 1155.
13.
PieperU., and StalkeD., Organometallics, 1993, 12, 1201.
14.
CoppensG., and NasielskiJ., Bull. Soc. Chim. Belges, 1962, 71, 5.
15.
ThummelR.P., and KohliD. K., J. Org. Chem., 1978, 43, 4882; R.P. Thummel and D.K. Kohli, Tetrahedron Lett., 1979, 143; R. P. Thummel, Tetrahedron, 1991, 47, 6851.