Abstract
The fundamental work of Weller and co-workers on the dynamic fluorescence quenching of singlet excited states of electron acceptors by donors with the generation of free radical ions and the Marcus treatment of these processes, that attempted to bring order into organic electron-transfer chemistry, can be considered as basic studies that, in the late '70s, gave the impulse to the development of the photoinduced electron-transfer oxygenation of several classes of organic compounds as a useful synthetic tool in peroxide chemistry. The enormous interest of this new mode of oxygen functionalization, that can be applied either to reactive substrates towards singlet oxygen or to those totally inert versus this intriguing electronic excited state of molecular oxygen, has been documented by numerous publications on this topic.
After a brief introduction on the singlet oxygenation, the first and more studied procedure of oxygen functionalization of unsaturated organic compounds, it shall be tried to present a brief overview of the theoretical work and of the sophisticated analytical techniques that support and permit the detection and characterization of the elusive radical ions involved in the P.E.T-oxygenation procedure. Following a short mechanistic orientation on the original Foote's proposal, there will be detailed, in relation to the peculiar physical properties of the sensitizers and organic compounds, the actual different mechanisms that can operate in these processes and how they can be controlled or modified upon the addition of inert reagents such as salts, aromatic hydrocarbons, quinones, and amines. From the synthetic point of view, this critical analysis appears of fundamental importance. In fact, although this area has been extensively reviewed in the last years, its potential as a synthetic tool in peroxide chemistry has not yet been stressed. In this regard, the search for new nonconventional sensitizers together with a simultaneous growing interest in organic syntheses that proceed via electron-transfer processes should greatly help in this effort.
Preview
Unable to display preview. Download preview PDF.
Similar content being viewed by others
10 References
Gollnick K, Schenck GO (1964) Pure Appl. Chem. 9: 507
Kavarnos GJ, Turro NJ (1986) Chem. Rev. 86: 401
Kautsky H (1939) Trans. Farad. Soc. 35: 216
Selinger HH (1960) Analyt. Biochem. 1: 60
Thompson QE (1961) J. Am. Chem. Soc. 83: 845
Brannan ME (1970) J. Chem. Soc., Chem. Comm. 956
Khan AU, Kasha MJ (1963) J. Chem. Phys. 39: 2105
Murray RW, Kaplan ML (1968) J. Am. Chem. Soc. 90: 537
Wasserman HH, Scheffer JR (1967) J. Am. Chem. Soc. 89: 3073
Peters JW, Pitts jr JN, Rosenthal I, Fuhr H (1972) J. Am. Chem. Soc. 94: 4348
Schaap AP, Thayer AL, Faler GR, Goda K, Kimura T (1974) J. Am. Chem. Soc. 96: 4025
Nonox JF (1961) Can. J. Phys. 39: 1110
Wayne RP (1969) Adv. Photochem. 7: 311
Corey EJ, Taylor WC (1964) J. Am. Chem. Soc. 86: 3881
Arnold SJ, Ogryzlo EA (1967) Can. J. Phys. 45: 2053
Scheffer JR, Ouchi MD (1970) Tetrahedron Lett. 223
Adam W (1975) Chem. Zeit. 99: 142
Schaap AP, Zaklika KA (1979), in: Wasserman HH, Murray RW (eds) Singlet Oxygen. Academic Press, New York, p 173
Frimer AA (1979) Chem. Rev. 79: 359
Adam W (1983), in: Patai S (ed) The Chemistry of Functional Groups, Peroxides. Wiley, NY, p 829
Blossey EC, Neckers DC, Thayer AL, Schaap AP (1970) J. Am. Chem. Soc. 95: 5820
Williams JR, Orton G, Unger LR (1973) Tetrahedron Lett. 4603
Nielsson R, Kearns DR (1974) Photochem. Photobiol. 19: 181
Foote CS, Dennery RW (1971) J. Am. Chem. Soc. 93: 5162
Kopecky KR, Reich HJ (1965) Can. J. Chem. 43: 2265
Gollnick K (1968) Adv. Photochem. 6: 1
Wilson T, Hastings JW (1970) in: Giese AC (ed) Photophysiology 5: 49, Academic Press, New York
Stevens B (1973) Acc. Chem. Res. 6: 90
Adam W, Epe B, Schiffmann D, Vargas F, Wild D (1988) Angew. Chem. 27: 429
Adam W, Bhushan V, Fuchs R, Kirckgassner U (1987) J. Org. Chem. 52: 3059
Schaap AP, Handley R, Giri BP (1987) Tetrahedron Lett. 28: 935
Schaap AP (1971) Tetrahedron Lett. 1757
Richardson WH, Hodge V (1970) J. Org. Chem. 35: 1216
Wieringa J, Strating J, Wynberg H, Adam W (1972) Tetrahedron Lett. 169
Bartlett PD, Ho MS (1974) J. Am. Chem. Soc. 96: 627
Schaap AP, Faler GR (1973) J. Am. Chem. Soc. 95: 3381
Jefford CW, Boschung AF (1977) Helv. Chem. Acta 60: 2673
Schaap AP, Recher SG, Faler GR, Villasenor SR (1983) J. Am. Chem. Soc. 105: 1691
Foote CS, Liu JWP (1968) Tetrahedron Lett. 3267
Foote CS, Dzakapasu AA, Liu JWP (1975) Tetrahedron Lett. 1247
Thomas MJ, Foote CS (1978) Photochem. Photobiol. 24: 683
Matsuura T, Yoshimura N, Nishinaga A, Saito I (1972) Tetrahedron 28: 4933
Gu CL, Foote CS, Kacher ML (1981) J. Am. Chem. Soc. 103: 5949
Landis ME, Madoux DC (1979) J. Am. Chem. Soc. 101: 5106
Ogryzlo EA, Tang CW (1970) J. Am. Chem. Soc. 92: 5034
Saito I, Matsuura T, Inoue K (1981) J. Am. Chem. Soc. 103: 188
Saito I, Matsuura T, Inoue K (1983) J. Am. Chem. Soc. 105: 3200
Peters G, Rodgers MAJ (1981) Biochem. Biophys. Acta 637
Chuang TS, Hoffman GW, Eisenthal KB (1974) Chem. Phys. Lett. 25: 201
Zaklika KA, Kaskar B, Schaap AP (1980) J. Am. Chem. Soc. 102: 386
Eberson L (1987) Electron Transfer Reactions in Organic Chemistry. Springer-Verlag, Heidelberg/Berlin/New York
Lowry TH, Richardson KS (1981) Mechanism and Theory in Organic Chemistry. Harper + Row, New York
Dimroth O (1933) Angew. Chem. 46: 571
Michaelis L (1935) Chem. Rev. 16: 243
Lewis GN, Lipkin D (1942) J. Am. Chem. Soc. 64: 2801
Weiss J (1941) Nature 147: 512
Hickling A (1942) Trans Faraday Soc. 38: 27
Lund H (1957) Acta Chem. Scan. 11: 1323
Rehm D, Weller A (1970) Isr. J. Chem. 8: 259
Guttenplan JB, Cohen SG (1972) J. Am. Chem. Soc. 94: 4040
Porter G (1963) in: Friess SL, Lewis ES, Weissenberger A (eds) Techniques of Organic Chemistry, 2nd edn, vol 8, Wiley Interscience, New York
Rebek JF (1982) Experimental Methods in Photochemistry and Photophysics. Wiley Interscience, New York, p 822
Kaptein R (1975) Adv. Free Radical Chem. 5: 319
Roth HD, Shilling MLM (1980) J. Am. Chem. Soc. 102: 4303
Turro NJ (1984) J. Photochem. 25: 69
Marcus RA (1964) Ann. Rev. Phys. Chem. 15: 155
Shaik SS (1985) Prog. Phys. Org. Chem. 15: 197
Pross A (1985) Acc. Chem. Res. 18: 212
Fox MA (1986) Adv. Photochem. 13: 237
Mariano PS (1984) in: Horspool WM (ed) Synthetic Organic Photochemistry. Plenum Press, New York, p 145
Mattes SL, Farid S (1983) in: Padwa A (ed) Organic Photochemistry, 6: 233, Dekker, New York
Mattay J (1987) Angew. Chem. Int. Ed. Engl. 26: 825
Koizumi M, Kato S, Mataga N, Matsuura T, Usui Y (1978) in: Photosensitized Reactions, Kagakudojiin Publ Co, Kyoto, Japan, Chaps 5, 11, 12
Eberson L (1982) Adv. Phys. Org. Chem. 18: 79
Parker VD (1984) Acc. Chem. Res. 17: 243
Turro NJ (1978) Modern Molecular Photochemistry. Chap 8, Benjamin/Cummings, Menlo Park CA
Ware WR, Holms JD, Arnold DR (1974) J. Am. Chem. Soc. 95: 861
Eberson L, Nyberg K (1966) J. Am. Chem. Soc. 88: 1686
Zweig A, Hodson WG, Jura WH (1964) J. Am. Chem. Soc. 86: 4124
Masuhara H, Mataga N (1981) Acc. Chem. Res. 14: 312
Mattes SL, Farid S (1983) J. Am. Chem. Soc. 195: 1386 J. Am. Chem. Soc. 108: 7356
Mataga N, Shioyama H, Kanda Y (1987) J. Phys. Chem. 91: 314
Gould IR, Moser JE, Ege D, Farid S (1988) J. Am. Chem. Soc. 110: 1991
Eriksen J, Foote CS, Parker TL (1977) J. Am. Chem. Soc. 99: 6455
Orbach N, Ottolenghi M (1975) in: Gordon M, Ware WR (eds) The Exciplex Academic Press, New York, p 75
Schomburg H, Staerk H, Weller A (1973) Chem. Phys. Lett. 22: 1
Mattes SL, Farid S (1980) J. Chem. Soc., Chem. Comm. 126
Saeva FD, Olin GR (1980) J. Am. Chem. Soc. 102: 299
Okada K, Hisanaritsu K, Mukai T (1981) Tetrahedron Lett. 22: 1251
Lopez L, Calò V (1984) J. Chem. Soc., Chem. Comm. 1266
Peover EM (1961) Nature 191: 702
McCullogh JJ, Miller RC, Fung D, Wu WS (1975) J. Am. Chem. Soc. 97: 5942
Chien CK, Wang HC, Szwarc M, Bard AJ, Itaya K (1980) J. Am. Chem. Soc. 102: 3100
Spada LT, Foote CS (1980) J. Am. Chem. Soc. 102: 391
Eriksen J, Foote CS (1980) J. Am. Chem. Soc. 102: 6083
Gollnick K, Schanatterer A (1984) Tetrahedron Lett. 25: 185, and 2735
Ando W, Kabe Y, Takata T (1982) J. Am. Chem. Soc. 104: 7314
Schaap AP, Zaklika KA, Kaskar B, Fung LMW (1980) J. Am. Chem. Soc. 102: 389
Mattes SL, Farid S (1980) J. Chem. Soc., Chem. Comm. 457
Berenjian N, deMayo P, Phoenix FH, Weedon AC (1979) Tetrahedron Lett. 4179
Ando W, Nagashima T, Saito K, Kohmoto S (1979) J. Chem. Soc., Chem. Comm. 154
Schaap AP, Anderson SD, Gagnon SD, Lopez L, Recher SG (1982) IX Symp. on Photochem. Pau (France) Abstract ST 15
Schaap AP, Lopez L, Anderson SD, Gagnon SD (1982) Tetrahedron Lett. 5493
Mizuno K, Kamiyama N, Ichinose N, Otsuji Y (1985) Tetrahedron 41: 2207
Griffin GW, Kirschenheuter GP, Vaz C, Umrigar PP, Lankin DC, Christensen S (1985) Tetrahedron 41: 2069
Brown-Wensley KA, Mattes SL, Farid S (1978) J. Am. Chem. Soc. 100: 4162
Futumara S, Kusunose S, Otha H, Kamiya Y (1984) J. Chem. Soc. Perkin Trans I 15
Schaap AP, Lopez L, Gagnon SD (1983) J. Am. Chem. Soc. 105: 663
Schaap AP, Siddiqui S, Prasad G, Palomino E, Lopez L (1984) J. Photochem. 25: 167
Gollnick K, Schanatterer A (1985) Tetrahedron Lett. 26: 173
Lopez L, Calò V, Aurora R (1986) J. Photochem. 32: 95
Lopez L (1985) Tetrahedron Lett. 26: 4383
Santamaria J, Ouchabane R (1986) Tetrahedron 42: 5559
Santamaria J, Ouchabane R, Rigaudy J (1989) Tetrahedron Lett. 30: 3977
Lopez L, Troisi L, Rashid SMK, Schaap AP (1989) Tetrahedron Lett. 30: 485
Akasaka T, Ando W (1987) J. Am. Chem. Soc. 109: 1260
Kabe Y, Takata T, Ueno K, Ando W (1984) J. Am. Chem. Soc. 106: 8174
Kopecky RK, Mumford C (1969) Can. J. Chem. 47: 709
Foote CS (1985) Tetrahedron 41: 2221
Nelsen SF (1987) Acc. Chem. Res. 20: 269
Clennan EL, Simmons W, Almgreen CW (1981) J. Am. Chem. Soc. 103: 2098
Numan H, Wieringa JH, Wynberg H, Hess J, Vos A (1977) J. Chem. Soc., Chem. Commun. 591
Krebs A, Schmalstieg H, Jarchow O, Klaska KH (1980) Tetrahedron Lett. 21: 3171
Manring LE, Erikson J, Foote CS (1980) J. Am. Chem. Soc. 102: 4275
Barton DHR, Leclerc G, Magnus PD, Menzies ID (1972) J. Chem. Soc., Chem. Commun. 447
Manring LE, Kramer MK, Foote CS (1984) Tetrahedron Lett. 25: 2523
Kwon BM, Foote CS, Khan SI (1989) J. Org. Chem. 54: 3378
Lopez L, Troisi L (1989) Tetrahedron Lett. 30: 485
Mattes SL, Farid S (1982) J. Am. Chem. Soc. 104: 1454
Maroulis AJ, Shigemitsu Y, Arnold DR (1978) J. Am. Chem. Soc. 100: 535
Jiang ZQ, Foote CS (1983) Tetrahedron Lett. 24: 461
Adam W, Arias LA, Zinner K (1983) Chem. Ber. 116: 839
Adam W, Arias LA, Scheutzow D (1982) Tetrahedron Lett. 23: 2835
Nelsen SF, Kapp DL, Teasley MF (1984) J. Org. Chem. 49: 579
Steichen DS, Foote CS (1981) J. Am. Chem. Soc. 103: 1855
Nelsen SF, Teasley MF, Kapp DL (1986) J. Am. Chem. Soc. 108: 5503
Gollnick K, Schnatterer A (1986) Photochem. Photobiol. 43: 365
Barton DHR, Haynes RK, Leclerc G, Magnus PD, Menzies ID (1975) J. Chem. Soc. Perkin Trans. 1: 2055
Haynes RK (1978) Aust. J. Chem. 31: 121, 131
Tang R, Yue HJ, Wolf JF, Mares F (1978) J. Am. Chem. Soc. 100: 5248
Farid S, Brown KA (1976) J. Chem. Soc., Chem. Commun. 564
Lopez L, Troisi L (1989) Tetrahedron Lett. 30: 3097
Delaunay J, Lebouc A, Tallec A, Simonet J (1982) J. Chem. Soc., Chem. Commun. 387
Gill GB, Hands D (1974) Tetrahedron Lett. 181
Haynes RK, Probert MKS, Wilmot ID (1978) Aust. J. Chem. 31: 1737
Curci R, Lopez L, Troisi L, Rashid SMK, Schaap AP (1987) Tetrahedron Lett. 28: 5319
Bell FA, Ledwith A, Sherrington DC (1969) J. Chem. Soc. (C) 2719
Eberson L, Larsson B (1986) Acta Chem. Scand. 40: 210
Belville DJ, Wirth DD, Bauld NL (1981) J. Am. Chem. Soc. 103: 718
Mann CK, Barnes KK (1970) Electrochemical Reactions in Nonaqueous Systems. Dekker, New York
Ouannes C, Wilson (1968) J. Am. Chem. Soc. 90: 6527
Goerner H, Schulte-Frohlinde D (1986) Chem. Phys. Lett. 124: 321
Lopez L, Lacerenza S (1987) XIIIth Int. Conf. of Photochem. Budapest, 9/14 August Abst 2P083
George MV, Kumar CV, Scaiano IC (1979) J. Phys. Chem. 83: 2452
Adam W, Platsch H, Schmidt E (1985) Chem. Ber. 118: 4385
Pagni RM (1984) Tetrahedron 40: 4161
Lopez L, Cal`o V, Stasi F (1987) Synthesis 947
Lopez L, Calò V (1985) Synthesis 774
Ciminale F, Lopez L (1985) Tetrahedron Lett. 26: 789
Schaap AP, Siddiqui S, Gagnon SD, Lopez L (1983) J. Am. Chem. Soc. 105: 5149
Schaap AP, Siddiqui S, Balakrishnan P, Lopez L, Gagnon SD (1983) Isr. J. Chem. 23:415
Schaap AP, Siddiqui S, Prasad G, Palomino E, Sandison M (1985) Tetrahedron 41:2229
Futumara S, Kusunose S, Ohta M, Kamiya Y (1982) J. Chem. Soc., Chem. Commun. 1223
Albini A, Arnold DR (1978) Can. J. Chem. 56: 2985
Griffin GW (1971) Angew. Chem., Int. Ed. Engl. 10: 537
Schaap AP, Siddiqui S, Prasad G, Raham AFM, Oliver JP (1984) J. Am. Chem. Soc. 106: 6087
Farid S, Hartmann SE, Evans TR (1975) in: Gordon M, Ware WR (eds) The Exciplexes. Academic Press, New York, p 327
Mattes SL, Farid S (1982) Acc. Chem. Res. 15: 80
Majima T, Pac C, Sakurai H (1980) J. Am. Chem. Soc. 102: 5265
Majima T, Pac C, Nakasone A, Sakurai H (1981) J. Am. Chem. Soc. 103: 4499
Lee GA (1978) J. Org. Chem. 43: 4256
Huisgen R, Mader H (1969) Angew. Chem., Int. Ed. Engl. 8: 604
Huisgen R, Markowski H (1976) Tetrahedron Lett. 4643
Trozzolo AM, Leslie TM, Sarpotdar AS, Small RD, Ferraudi GJ, Do Minh T, Harless RL (1979) Pure Appl. Chem. 51: 261
Clawson P, Lunn PM, Whiting DA (1984) J. Chem. Soc., Chem. Commun. 134
Wong JPK, Fahmi AA, Griffin GW, Bhacca NS (1981) Tetrahedron 37: 3354
Miyashi T, Kamata M, Mukai T (1986) J. Chem. Soc., Chem. Commun. 1577
Miyashi T, Kamata M, Mukai T (1986) J. Am. Chem. Soc. 108: 2755
Ulmann EF, Henderson Jr WA (1967) J. Am. Chem. Soc. 89: 4390
Saveant JM (1980) Acc. Chem. Res. 113: 19
Schaap AP, Prasad G, Gagnon SD (1983) Tetrahedron Lett. 3047
Schaap AP, Prasad G, Siddiqui S (1984) Tetrahedron Lett. 3035
Sakuragi M, Sakuragi H (1980) Chem. Lett. 1017
Landis M, Madoux DC (1979) J. Am. Chem. Soc. 101: 5106
Akaba R, Aihara S, Sakuragi H, Tokumaru K (1987) J. Chem. Soc., Chem. Commun. 1262
Nicholson RS, Shain I (1964) Anal. Chem. 36: 706
Okada K, Hisamitsu K, Mukai T (1981) Tetrahedron Lett. 22: 1251
Okada K, Hisamitsu K, Miyashi T, Mukai T (1982) J. Chem. Soc., Chem. Commun. 974
Calò V, Lopez L., Pesce G, Todesco PE (1973) Tetrahedron 29: 1625
Calò V, Lopez L, Fiandanese V, Naso F, Ronzini L (1978) Tetrahedron Lett. 4693
Brisimitzakis AC, Schuster DI (1982) Tetrahedron Lett. 23: 4531, 4534
Schuster DI (1978) Accounts Chem. Res. 19: 3329
Lopez L (1987) Conference on Photochem. Como 12/14 Sept. Abst. CO4
Roth HD, Schilling MLM (1979) J. Am. Chem. Soc. 101: 1898
Roth HD, Schilling MLM (1980) J. Am. Chem. Soc. 102: 4303
Roth HD, Schilling MLM (1981) J. Am. Chem. Soc. 103: 7210
Roth HD, Schilling MLM, Jones G (1981) J. Am. Chem. Soc. 103: 1246
Haselbach E, Vauthey E, Suppan P (1988) Tetrahedron 44: 7335
Hilinski EF, Milton SV, Rentzepis PM (1983) J. Am. Chem. Soc. 105: 5196
Foote CS, Burns PA, Mazur S, Lerdal D (1973) J. Am. Chem. Soc. 95: 586
Matsumoto M, Kuroda K (1979) Tetrahedron Lett. 1607
Steichen DS, Foote CS (1979) Tetrahedron Lett. 4363
Eriksen J, Foote CS (1978) J. Phys. Chem. 82: 2654
Manring LE, Gu CI, Foote CS (1983) J. Phys. Chem. 87: 40
Dobrowolski DC, Ogilby PR, Foote CS (1983) J. Phys. Chem. 87: 2261
Ogilby PR, Foote CS (1983) J. Am. Chem. Soc. 105: 3423
Araki Y, Dobrowolski DC, Goyne TE, Hanson DC, Jiang ZQ, Lee KJ, Foote CS (1984) J. Am. Chem. Soc. 106: 4570
Albini A, Spreti S (1985) Gazz. Chim. Ital. 115: 227
Santamaria J (1981) Tetrahedron Lett. 22: 4511
Santamaria J, Gabillet P, Bokobza L (1984) 25: 2139
Van Den Heuvel CJM, Streinberg H, de Boer TJ, Roy J (1980) Neth. Chem. Soc. 99: 109
Rigaudy J, Maumy M (1972) Bull. Soc. Chim. Fr. 3936
Wei SK, Adelman AH (1969) Tetrahedron Lett. 3297
Albini A, Spreti S (1987) J. Chem. Soc. Perkin Trans. II 1175
Saito I, Tamoto K, Matsuura T (1979) Tetrahedron Lett. 2855
Reichel LW, Griffin GW, Muller AJ, Das PK, Ege SN (1984) Can. J. Chem. 62: 424
Davis HF, Das PK, Reichel LW, Griffin GW (1984) J. Am. Chem. Soc. 106: 6968
Fox MA (1987) Top. Curr. Chem. 142: 72
Bard AJ (1982) J. Phys. Chem. 86: 172
Wrighton MS (1979) Acc. Chem. Res. 12: 303
Mozzanega MN, Herrmann JM, Pichat P (1977) Tetrahedron Lett. 2965
Kanno T, Oguchi T, Sakuragi H, Tokumaru K (1980) Tetrahedron Lett. 467
Fox MA, Liding B, Chen CC (1982) J. Am. Chem. Soc. 104: 5828
Fox MA, Chen CC (1983) Tetrahedron Lett. 24: 547
Davidson RS, Pratt JE (1983) Tetrahedron Lett. 24: 5903
Hussein FH, Rudham R (1984) J. Chem. Soc. Faraday Trans. I. 80: 2817
Hirdchwald WH (1985) Acc. Chem. Res. 18: 228
Okamoto K, Yamamoto Y, Tanaka H, Itaya A (1985) Bull. Chem. Soc. Japan 58: 2015
Fox MA, Younathan JN (1986) Tetrahedron 42: 6285
Pavlik JW, Tantayanon S (1981) J. Am. Chem. Soc. 103: 6755
Gerischer H, Willig F (1976) Top. Curr. Chem. 61: 33
Kabir-ud Din, Owen RC, Fox MA (1981) J. Phys. Chem. 85: 1679
Westheimer F (1985) Adv. Phys. Org. Chem. 21: 1
Author information
Authors and Affiliations
Editor information
Rights and permissions
Copyright information
© 1990 Springer-Verlag
About this paper
Cite this paper
Lopez, L. (1990). Photoinduced electron transfer oxygenations. In: Mattay, J. (eds) Photoinduced Electron Transfer I. Topics in Current Chemistry, vol 156. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-52379-0_5
Download citation
DOI: https://doi.org/10.1007/3-540-52379-0_5
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-52379-6
Online ISBN: 978-3-540-46976-6
eBook Packages: Springer Book Archive