Abstract
Photochemical excitation may induce intermolecular electron-transfer. Thus an electron donor-acceptor couple can be activated by light which then transforms an inert substrate by enhancing its redox properties. This is particularly significant if a very efficient process or a chain reaction follows the initial activation induced by electron-transfer.
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References
M. Julliard and M. Chanon, Chem. Rev. 82 (1983) 425.
M. Julliard and M. Chanon, Chem. Scr. 24 (1984) 11.
M. Chanon, Bull. Soc. Chim. Fr., 2 (1985) 209.
M. Chanon, Acc. Chem. Res., (1987) 214.
P. Nelleborg, H. Lund and J. Eriksen, Tetrahedron Lett. 26 (1985) 1773.
M. Kojima, H. Sakuragi and K. Tokumaru, Bull. Chem. Soc. Jpn. 58 (1981) 521.
C. Amatore and J.M. Saveant, J. Electroanal. Chem. Interfacial Electrochem. 126.(1981) 1.
J.M. Saveant, Acc. Chem. Res., 13 (1980) 323.
C. Amatore, J. Pinson, J.M. Saveant and A. Thiebault, J. Am. Chem. Soc. 103 (1981) 6930.
J. Pinson and J.M. Saveant, J. Chem. Soc. Chem. Commun. (1974) 933.
J. Pinson and J. M. Saveant, J. Am. Chem. Soc., 100 (1978) 1506.
W. J. M. van Tilborg and C.J. Smit, Tetrahedron Lett., (1977) 3651.
W.J.M. van Tilborg, C. J. Smit and J. J. Scheele, Tetrahedron Lett., (1978) 776.
H. Tagaya, T. Aruga, O. Ito and M. Matsuda, J. Am. Chem. Soc. 103, (1981) 5484.
D.R. Stranks and J.K. Yandell, J. Phys. Chem., 73 (1969) 840.
D. R. Stranks and J. K. Yandell, Exch. React. Proc. Symp. (1965) 83.
L. M. Tolbert J. Am. Chem. Soc., 102 (1980) 6808.
E.S. Huyser, “Free Radical Chain Reactions”, Wiley Intersciences New York, N. Y. (1970) p 44.
J.F. Bunnett “Investigation of Rates and Mechanisms of Reactions” 3rd ed., Part 1, E.S. Lewis Ed., Wiley, New York, N. Y. (1974) p 381.
A. W. Adamson and A. H. Sporer, J. Am. Chem. Soc., 80 (1958) 3865.
S. Hoz and J.F. Bunnett, J. Am. Chem. Soc. 99 (1977) 4690.
E.S. Huyser “Free-Radical Chain Reactions”, Wiley Intersciences New York, N. Y. (1970) p 51.
B. Helgee and V.D. Parker, Acta Chemica Scandinavica, B 34, (1980) 129.
M. Chanon and L. Eberson, “Photochemistry of Homogeneous and Heterogeneous Gears Involving Electron Transfer Catalysis” in Photoinduced Electron Transfer, M.A. Fox and M. Chanon Eds., Elsevier, Amsterdam (1988), Vol. A, p 409.
A. Albini and D.R. Arnold, Can. J. Chem., 56 (1978) 2985.
M. Yasuda, T. Yamashita, T. Matsumoto, K. Shima and C. Pac, J. Org. Chem., 19 (1985) 3667.
S. Fukuzumi, S. Kuroda and T. Tanaka, J. Chem. Soc. Chem. Commun., (1987) 120.
K. Gollnick and A. Schnatterer, Tetrahedron Lett., 26(1985) 173.
D. Rehm and A. Weiler, Isr. J. Chem. 8 (1970) 259.
S. Steenken in “Free Radicals Chemistry, Pathology and Médecine” Vol 3, Rice Evans and Dormonty T. Eds., Richilieu Press London (1987).
E. Bothe, G. Behrens and D. Schulte-Frolhinde, Z. Naturforsch. 32b (1977) 886.
A.P. Schaap, S. Siddiqui, D. Gagnon and L. Lopez, J. Am. Chem. Soc., 105 (1983) 5149.
A.P. Schaap, L. Lopez, S.D. Anderson and S.D. Gagnon, Tetrahedron Lett., 23 (1982) 5493.
A.P. Schaap, L. Lopez and S.D. Gagnon, J. Am. Chem. Soc., 105 (1983) 663.
J. Santamaria, “Photoinduced Electron-Transfer”, M.A. Fox and M. Chanon Eds., Elsevier, Amsterdam (1988), Vol. B, p 483.
M. Julliard,“Photoinduced Electron-Transfer”, M.A. Fox and M. Chanon Eds., Elsevier, Amsterdam (1988), Vol. B, p 216.
A. Albini and S. Spreti, Z. Naturforsch.. 41B (1986) 1286.
I. Saito, K. Tamoto and T. Matsuura, Tetrahedron Lett., 31 (1979) 2889.
A.M. De Nicholas and D.A. Arnold, Can. J. Chem., 60 (1982) 2165.
K. Schested, J. Holemen and E.J. Hart, J. Phys. Chem., 81 (1977) 1363.
K. Schested and J. Holeman, J. Phys. Chem., 82 (1978) 651.
D.T. Sawyer, E.J. Nanni and J.L. Roberts, “Electrochemical and Spectrochemical Studies of Biological Redox Compounds” K.M. Kadish Ed., Adv. Chem. Ser. n• 21, ACS 1982 p 585.
S.L. Mattes and S. Farid, J. Am. Chem. Soc. 108.(1986) 7356.
F.D. Lewis and J.R. Petisce, Tetrahedron, 42 (1986) 6207.
I.M. Kolthoff and A.I. Medalia, J. Am. Chem. Soc. 71 (1949) 3789.
A. J. Everett and G.J. Minkoff, Trans. Faraday Soc. 49 (1953) 410.
B. Maillard, K.U. Ingold and J.C. Scaiano, J. Am. Chem. Soc., 105 (1983) 5095.
R.O.C. Norman, C.B. Thomas and P.J. Ward, J. Chem. Soc. Perkin Trans I, 23 (1973) 2914.
S. Uemara, T. Ikeda, S. Tanaka and M. Okano, J. Chem. Soc. Perkin Trans II, 10 (1979) 2574.
O. Hammerich and V.D. Parker, Adv. Phys. Org. Chem., 20 (1984) 55.
C. Walling, D.M. Camaioni and S.S. Kim, J. Am.Chem. Soc., 100 (1978) 4814.
J. Bonnard and G. Poilane, Rhone Poulenc, US Patent 3,387,036 (June 4, 1968).
Jouffret, Rhone Poulenc Textile, US Patent 3,948,995 (April 6, 1976).
F. Chanon and M. Chanon in “Photocatalysis” E. Pelizetti and N. Serpone Eds., Wiley, New York, N. Y., (1988).
E. Baciocchi, T. Del Giacco, C. Rol and G.V. Sebastiani, Tetrahedron Lett., 26 (1985) 3353.
G.V. Sebastiani, Tetrahedron Lett., 26 (1985) 3353.
I. Saito, T. Matsuura and K. Inoue, J. Am. Chem. Soc., 105 (1983) 3200.
G. Crank and M.I.H. Makin, Aust. J. Chem., 32 (1984) 845.
R. Barone and M. Chanon, “Computer Aids to Chemistry”, G. Vernin and M. Chanon Ed., Horwood-Wiley, Chichester, New-York, 1986, p19.
A.E. Williams, Encyclopedia of Chemical Technology, Kirk-Othmer, Wiley, New-York, 1978, p736.
J.C. Brunic, M. Costantini, N. Crenne, M. Jouffret, (Rhône-Poulenc)U.S.Pat.3, 658, 875, Apr 25, 1972.
M. Nakada, C. Miura, K. Ogawa, R. Hayashida, S. Fukushi, M. Hirota, T. Ishi, Kenkyu Hokoku-Chiba Kogyo Daigaku, Riko-hen, 32, 27(1987).
B. Jonson, R. Larsson and B. Rebenstorf, J. Catal., 102, 29 (1986).
A. Monaci, Gazz. Chim. Ital., 116, 339 (1986).
P.J. Van der Berg, K. Van der Wiele, J.J.J. Den Ridder, Int. Congr. Cat. 5Proced.) 8th, 1984, 5, V393, Verlag Chemie Weinheim.
P. Maggioni, F. Minisci, Chimica e l’Industria, 61, 101(1979).
C. Walling, C. Zhao, G.M. El Taliani, J. Org. Chem., 48, 4910 (1983).
G.B. Shulpin, P. Lederer and E. Macova, Izv. Akad. Nauk. SSR, Ser. Khim., 2638 (1986).
M. Fujihara, Y. Satoh, T. Osa, Bull. Chem. Soc. Jpn, 55, 666 (1982).
D. Pletcher, Chem. and Ind., 358 (1982).
D. Degner, “Techniques of Chemistry”, Ed. N.L. Weinber and B.V. Tilak, J. Wiley, New-York, 1982, p 251.
R. Clarke, A.T. Kunh and E. Okoh, Chem. in Britain, 11, 2, 59 (1975).
J. Chaussard, l’Actualité Chimique, 29 (Nove. 1982).
J.H. Wagenknecht, Angew. Chem. Int. Ed., 25, 683 (1986).
R.P. Kreh, R.M. Spotnitz and J.T. Lundquist, Tet. Letters, 28, 1067 (1987).
R.P. Kreh, R.M. Spotnitz (W.R. Grace and Co) U.S. US 4, 647, 349 March 3 1987.
E. Steckhan, Angew. Chem. Inter. Ed., 25, 683 (1986).
G. Kreysa, H. Medin, J. Appl. Electrochemistry, 16, 757 (1986) and references therein.
J.J. Jow, A.C. Lee and T.C. Chou, J. Appl. Electrochem., 17, 753 (1987).
Ger. Offen 2 848 397 (1980).
Ger. Offen 2 851 732 (1980).
Ger. Offen 2 912 058 (1980).
US Patent 4 212 711 (1980).
Ger. Offen 2 435 985 (1975).
K.B. Wiberg, “Oxidation in Organic Chemistry”, K.B. Wiberg Ed., Vol 5A, p 94.
F. Minisci, A. Citterio, C. Giordano, Acc. Chem. Res., 16, 27 (1983).
I. Nishigushi, T. Hirashima, J.Org.Chem., 50, 539 (1985)
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Galadi, A., Julliard, M., Chanon, M. (1989). Electron-Transfer Photosensitization in the Oxidation of Alkyl Aromatics and Heteroaromatics. In: Minisci, F. (eds) Free Radicals in Synthesis and Biology. NATO ASI Series, vol 260. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0897-0_17
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DOI: https://doi.org/10.1007/978-94-009-0897-0_17
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