Abstract
Electron transfer between organic molecules, almost non existent in the ground state, is common occurrence when an excited state is involved. The innovative characteristics of (photoinduced) single electron transfer between organic molecules are discussed in the frame of the general mechanism of organic chemistry. The redox step generates a pair of oppositely charged radical ions under exceptionally mild conditions in neat organic solvent by irradiation. These hitherto little investigated species show a rich and varied chemistry. Representative examples are illustrated, in particular photoinduced radical conjugate alkylation using unconventional radical precursors. The versatility of the photochemical method for radical ions generation suggests that it may give a significant contribution to the development of organic synthesis in the next years.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
J. Mattay, A. Griesbeck, Eds. Photochemical Key Steps in Organic Synthesis, VCH, Weinheim, 1998.
W. H. Horspool, P. S. Song, Eds. CRC Handbook of Organic Photochemistry and Photobiology, CRC Press, Boca Raton, 1995.
W. Horspool, D. Armesto, Organic Photochemistry: a Comprehensive Treatment, Ellis Horwood, New York, 1992.
D. Rehm, A. Weiler, Isr. J. Chem., 1970, 8, 259.
M. A. Fox, M. Chanon, Eds. Photoinduced Electron Transfer, Elsevier, Amsterdam, 1988.
G. J. Kavarnos, N. J. Turro, Chem. Rev., 1986, 86, 401.
G. J. Kavarnos, Top. Curr. Chem., 1991, 156, 21
J. Mattay, Ed., Top. Curr. Chem., 1990, 156; 1990, 158; 1991, 159; 1992, 163; 1993, 168.
L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Berlin, 1987.
P. S. Mariano, Ed. Advances in Electron Transfer Chemsitry, JAI Press, Greenwich, CT, 1991–1998, Vol. 1–6.
A. Pross, S. S. Shaik. Acc. Chem. Res., 1983, 16, 363.
W. Schlenck, E. Bergmann, Liebigs. Ann. Chem., 1928, 464, 1.
D. Caine, Org. React, 1976, 23, 1.
L. Eberson, R. Gonzalez-Luque, M. Merchan, F. Radner, B. O. Roos, S. Shaiks, J. Chem. Soc., Perkin Trans. 2, 1997, 463.
L. Eberson, M. P. Hartshorn, F. Radner, M. Merchan, B. O. Roos. Acta. Chem. Scand., 1993, 47, 176.
J. Ko, G. B. Schuster, J. Am. Chem. Soc., 1977, 99, 6107.
S. G. Cohen, A. Parola, G. H. Parsons, Chem. Rev., 1973, 73, 141.
J. Cossy, J. P. Pete, inref. 9, Vol 5, p. 141.
I. R. Gould, D. Ege, J. E. Moser, S. Fand, J. Am. Chem. Soc., 1990, 112, 4290.
M. Freccero, M. Mella, A. Albini Tetrahedron 1994, 50, 2115.
M. A. Keller, D. G. Whitten, I. R. Gould, W. R. Bergmark, J. Am. Chem. Soc., 1991, 113, 358.
M. Mella, M. Fagnoni, M. Freccero, E. Fasani, A. Albini, Chem. Rev., 1998, 27, 81.
A. Albini, M. Mella, M. Freccero, Tetrahedron, 1994, 50, 575.
A. Albini, E. Fasani, M. Mella, Top. Curr. Chem., 1993, 168, 143.
U. C. Yoon, P. S. Mariano, Acc. Chem. Res., 1992, 25, 233.
E. R. Gaillard, D. G. Whitten, Acc. Chem. Res., 1996, 29, 292.
R. Popielartz, D. R. Arnold, J. Am. Chem. Soc, 1990, 112, 3068.
F. D. Lewis, Acc. Chem. Res., 1986, 29, 520.
I. R. Gould, S. Farid, Acc. Chem. Res., 1996, 29, 520.
K. Mizuno, Y. Otsuji, Top. Curr. Chem., 1994, 169, 301.
G. Pandey, Top. Curr. Chem., 1993, 168, 175.
P. Maslak, Top. Curr. Chem., 1993, 168, 1.
F. D. Saeva, Top. Curr. Chem., 1991, 156, 59.
C. F. Guertler, S. Blechert, E. Steckhan, Synlett, 1994, 141.
T. Hirao, Synlett., 1999, 175.
M. Yasuda, C. Pac, H. Sakurai, J. Org. Chem., 1981, 46, 788.
M. Mella, E. Fasani, A. Albini, Tetrahedron, 1991, 47, 3137.
B. Giese, Radicals in Organic Synthesis. Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986.
D. P. Curran, in B. M. Trost, I. Fleming, Comprehensive Organic Synthesis, Pergamon, Oxford, 1991, Vol. 6, p. 714.
B. B. Snider, Chem. Rev., 1996, 96, 339.
V. Nair, J. Mathew, J. Prabhakaran, Chem. Soc. Rev., 1997, 97, 127.
M. Fagnoni, M. Mella, A. Albini, J. Am. Chem. Soc., 1995, 117, 7877.
M. Fagnoni, M. Mella, A. Albini, J. Org. Chem., 1994, 59, 5614.
M. Fagnoni, M. Mella, A. Albini, Tetrahedron, 1995, 51, 859.
M. Fagnoni, M. Mella, A. Albini, J. Org. Chem., 1998, 63, 4026
A. Albini, S. Spreti, J. Chem. Soc., Chem. Commun., 1986, 1426.
L. Cermenati, M. Mella, A. Albini, Tetrahedron, 1998, 54, 2575.
L. Cermenati, C. Richter, A. Albini, J. Chem. Soc., Chem. Commun., 1998, 805.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2000 Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
Albini, A., Fagnoni, M., Mella, M. (2000). Photoinduced Electron Transfer: Perspectives in Organic Synthesis. In: Fabbrizzi, L., Poggi, A. (eds) Chemistry at the Beginning of the Third Millennium. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-04154-3_5
Download citation
DOI: https://doi.org/10.1007/978-3-662-04154-3_5
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-08687-8
Online ISBN: 978-3-662-04154-3
eBook Packages: Springer Book Archive