Abstract
Since the classical studies by Ingold in the nineteen thirties the mechanism of the aliphatic nucleophilic substitution reaction has been described as a polar two-electron mechanism in which the nucleophile transfers two electrons to the new bond which is established to the electrophilic center. Depending on the reaction order the abbreviations SN1 and SN2 were used for first-order and second-order reactions, respectively.
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N. Kornblum, R.E. Michel, and R.C. Kerber, J. Am. Chem. Soc. 88: 5660, 5662 (1966).
N. Kornblum, Angellw. Chem. 87: 797 (1975).
G.A. Russell and W.C. Danen, J. Am. Chem. Soc. 88: 5663 (1966).
G.A. Russell, M. Jawdosiuk, and M. Makosza, J. Am. Chem. Soc. 101: 2355 (1979).
G.A. Russell and G.W. Holland, J. Am. Chem. Soc. 91: 3967 (1969).
H.R. Ward, R.G. Lawler, and R.A. Cooper, J. Am. Chem. Soc. 91: 746 (1969).
A.R. Lepley and R.L. Landau, J. Am. Chem. Soc. 91: 748 (1969).
S. Bank and D.A. Noyd, J. Am. Chem. Soc. 95: 8203 (1973).
J.F. Garst, Acc. Chem. Res. 4:400 (1971) and references therein.
S. Bank and D.A. Juckett, J. Am. Chem. Soc. 89: 7742 (1976).
H. Lund, M.A. Michel, and J. Simonet, Acta Chem. Scand. B28: 900 (1974).
J. Simonet, M.A. Michel, and H. Lund, Acta Chem. Scand. B29: 489 (1975).
H. Lund and J. Simonet, J. Electroanal. Chem. 65: 205 (1975).
H. Lund, J. Mol. Cat. 38: 203 (1986).
H. Lund and L.H. Kristensen, Acta Chem. Scand. B33: 495 (1979).
L. Eberson, Acta Chem. Scand. B38: 439 (1984).
T. Lund and H. Lund, Acta Chem. Scand. B40: 470 (1986);
T. Lund and H. Lund, Acta Chem. Scand. B41: 93 (1987);
T. Lund and H. Lund, Acta Chem. Scand. B42: 269 (1988).
K. Daasbjerg, T. Lund, and H. Lund, Tetrahedron Lett. 30: 493 (1989).
R. Fuhlendorff, D. Occhialini, S.U. Pedersen, and H. Lund, Acta Chem. Scand. B43 (1989), 803.
T. Lund, S.U. Pedersen, H. Lund, K.M. Cheung, and J.H.P. Utley, Acta Chem. Scand. B41: 285 (1987).
A. Pross and S.S. Shaik, Acc. Chem. Res. 16: 363 (1983).
A. Pross, Acc. Chem. Res. 18: 212 (1985).
J.F. Bunnett, Acc. Chem. Res. 11: 413 (1978).
J.-M. Savéant, Acc. Chem. Res. 13: 323 (1980).
L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer Verlag, Berlin, Heidelberg (1987)
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© 1990 Plenum Press, New York
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Lund, H. (1990). Single Electron Transfer in Aliphatic Nucleophilic Substitution. In: Chatgilialoglu, C., Asmus, KD. (eds) Sulfur-Centered Reactive Intermediates in Chemistry and Biology. NATO ASI Series, vol 197. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5874-9_8
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DOI: https://doi.org/10.1007/978-1-4684-5874-9_8
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