Skip to main content
SpringerLink
Log in

Photoinduced electron transfer oxygenations

  • Conference paper
  • First Online:
Photoinduced Electron Transfer I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 156))

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

10 References

  1. Gollnick K, Schenck GO (1964) Pure Appl. Chem. 9: 507

    Google Scholar 

  2. Kavarnos GJ, Turro NJ (1986) Chem. Rev. 86: 401

    Google Scholar 

  3. Kautsky H (1939) Trans. Farad. Soc. 35: 216

    Google Scholar 

  4. Selinger HH (1960) Analyt. Biochem. 1: 60

    Google Scholar 

  5. Thompson QE (1961) J. Am. Chem. Soc. 83: 845

    Google Scholar 

  6. Brannan ME (1970) J. Chem. Soc., Chem. Comm. 956

    Google Scholar 

  7. Khan AU, Kasha MJ (1963) J. Chem. Phys. 39: 2105

    Google Scholar 

  8. Murray RW, Kaplan ML (1968) J. Am. Chem. Soc. 90: 537

    Google Scholar 

  9. Wasserman HH, Scheffer JR (1967) J. Am. Chem. Soc. 89: 3073

    Google Scholar 

  10. Peters JW, Pitts jr JN, Rosenthal I, Fuhr H (1972) J. Am. Chem. Soc. 94: 4348

    Google Scholar 

  11. Schaap AP, Thayer AL, Faler GR, Goda K, Kimura T (1974) J. Am. Chem. Soc. 96: 4025

    Google Scholar 

  12. Nonox JF (1961) Can. J. Phys. 39: 1110

    Google Scholar 

  13. Wayne RP (1969) Adv. Photochem. 7: 311

    Google Scholar 

  14. Corey EJ, Taylor WC (1964) J. Am. Chem. Soc. 86: 3881

    Google Scholar 

  15. Arnold SJ, Ogryzlo EA (1967) Can. J. Phys. 45: 2053

    Google Scholar 

  16. Scheffer JR, Ouchi MD (1970) Tetrahedron Lett. 223

    Google Scholar 

  17. Adam W (1975) Chem. Zeit. 99: 142

    Google Scholar 

  18. Schaap AP, Zaklika KA (1979), in: Wasserman HH, Murray RW (eds) Singlet Oxygen. Academic Press, New York, p 173

    Google Scholar 

  19. Frimer AA (1979) Chem. Rev. 79: 359

    Google Scholar 

  20. Adam W (1983), in: Patai S (ed) The Chemistry of Functional Groups, Peroxides. Wiley, NY, p 829

    Google Scholar 

  21. Blossey EC, Neckers DC, Thayer AL, Schaap AP (1970) J. Am. Chem. Soc. 95: 5820

    Google Scholar 

  22. Williams JR, Orton G, Unger LR (1973) Tetrahedron Lett. 4603

    Google Scholar 

  23. Nielsson R, Kearns DR (1974) Photochem. Photobiol. 19: 181

    Google Scholar 

  24. Foote CS, Dennery RW (1971) J. Am. Chem. Soc. 93: 5162

    Google Scholar 

  25. Kopecky KR, Reich HJ (1965) Can. J. Chem. 43: 2265

    Google Scholar 

  26. Gollnick K (1968) Adv. Photochem. 6: 1

    Google Scholar 

  27. Wilson T, Hastings JW (1970) in: Giese AC (ed) Photophysiology 5: 49, Academic Press, New York

    Google Scholar 

  28. Stevens B (1973) Acc. Chem. Res. 6: 90

    Google Scholar 

  29. Adam W, Epe B, Schiffmann D, Vargas F, Wild D (1988) Angew. Chem. 27: 429

    Google Scholar 

  30. Adam W, Bhushan V, Fuchs R, Kirckgassner U (1987) J. Org. Chem. 52: 3059

    Google Scholar 

  31. Schaap AP, Handley R, Giri BP (1987) Tetrahedron Lett. 28: 935

    Google Scholar 

  32. Schaap AP (1971) Tetrahedron Lett. 1757

    Google Scholar 

  33. Richardson WH, Hodge V (1970) J. Org. Chem. 35: 1216

    Google Scholar 

  34. Wieringa J, Strating J, Wynberg H, Adam W (1972) Tetrahedron Lett. 169

    Google Scholar 

  35. Bartlett PD, Ho MS (1974) J. Am. Chem. Soc. 96: 627

    Google Scholar 

  36. Schaap AP, Faler GR (1973) J. Am. Chem. Soc. 95: 3381

    Google Scholar 

  37. Jefford CW, Boschung AF (1977) Helv. Chem. Acta 60: 2673

    Google Scholar 

  38. Schaap AP, Recher SG, Faler GR, Villasenor SR (1983) J. Am. Chem. Soc. 105: 1691

    Google Scholar 

  39. Foote CS, Liu JWP (1968) Tetrahedron Lett. 3267

    Google Scholar 

  40. Foote CS, Dzakapasu AA, Liu JWP (1975) Tetrahedron Lett. 1247

    Google Scholar 

  41. Thomas MJ, Foote CS (1978) Photochem. Photobiol. 24: 683

    Google Scholar 

  42. Matsuura T, Yoshimura N, Nishinaga A, Saito I (1972) Tetrahedron 28: 4933

    Google Scholar 

  43. Gu CL, Foote CS, Kacher ML (1981) J. Am. Chem. Soc. 103: 5949

    Google Scholar 

  44. Landis ME, Madoux DC (1979) J. Am. Chem. Soc. 101: 5106

    Google Scholar 

  45. Ogryzlo EA, Tang CW (1970) J. Am. Chem. Soc. 92: 5034

    Google Scholar 

  46. Saito I, Matsuura T, Inoue K (1981) J. Am. Chem. Soc. 103: 188

    Google Scholar 

  47. Saito I, Matsuura T, Inoue K (1983) J. Am. Chem. Soc. 105: 3200

    Google Scholar 

  48. Peters G, Rodgers MAJ (1981) Biochem. Biophys. Acta 637

    Google Scholar 

  49. Chuang TS, Hoffman GW, Eisenthal KB (1974) Chem. Phys. Lett. 25: 201

    Google Scholar 

  50. Zaklika KA, Kaskar B, Schaap AP (1980) J. Am. Chem. Soc. 102: 386

    Google Scholar 

  51. Eberson L (1987) Electron Transfer Reactions in Organic Chemistry. Springer-Verlag, Heidelberg/Berlin/New York

    Google Scholar 

  52. Lowry TH, Richardson KS (1981) Mechanism and Theory in Organic Chemistry. Harper + Row, New York

    Google Scholar 

  53. Dimroth O (1933) Angew. Chem. 46: 571

    Google Scholar 

  54. Michaelis L (1935) Chem. Rev. 16: 243

    Google Scholar 

  55. Lewis GN, Lipkin D (1942) J. Am. Chem. Soc. 64: 2801

    Google Scholar 

  56. Weiss J (1941) Nature 147: 512

    Google Scholar 

  57. Hickling A (1942) Trans Faraday Soc. 38: 27

    Google Scholar 

  58. Lund H (1957) Acta Chem. Scan. 11: 1323

    Google Scholar 

  59. Rehm D, Weller A (1970) Isr. J. Chem. 8: 259

    Google Scholar 

  60. Guttenplan JB, Cohen SG (1972) J. Am. Chem. Soc. 94: 4040

    Google Scholar 

  61. Porter G (1963) in: Friess SL, Lewis ES, Weissenberger A (eds) Techniques of Organic Chemistry, 2nd edn, vol 8, Wiley Interscience, New York

    Google Scholar 

  62. Rebek JF (1982) Experimental Methods in Photochemistry and Photophysics. Wiley Interscience, New York, p 822

    Google Scholar 

  63. Kaptein R (1975) Adv. Free Radical Chem. 5: 319

    Google Scholar 

  64. Roth HD, Shilling MLM (1980) J. Am. Chem. Soc. 102: 4303

    Google Scholar 

  65. Turro NJ (1984) J. Photochem. 25: 69

    Google Scholar 

  66. Marcus RA (1964) Ann. Rev. Phys. Chem. 15: 155

    Google Scholar 

  67. Shaik SS (1985) Prog. Phys. Org. Chem. 15: 197

    Google Scholar 

  68. Pross A (1985) Acc. Chem. Res. 18: 212

    Google Scholar 

  69. Fox MA (1986) Adv. Photochem. 13: 237

    Google Scholar 

  70. Mariano PS (1984) in: Horspool WM (ed) Synthetic Organic Photochemistry. Plenum Press, New York, p 145

    Google Scholar 

  71. Mattes SL, Farid S (1983) in: Padwa A (ed) Organic Photochemistry, 6: 233, Dekker, New York

    Google Scholar 

  72. Mattay J (1987) Angew. Chem. Int. Ed. Engl. 26: 825

    Google Scholar 

  73. Koizumi M, Kato S, Mataga N, Matsuura T, Usui Y (1978) in: Photosensitized Reactions, Kagakudojiin Publ Co, Kyoto, Japan, Chaps 5, 11, 12

    Google Scholar 

  74. Eberson L (1982) Adv. Phys. Org. Chem. 18: 79

    Google Scholar 

  75. Parker VD (1984) Acc. Chem. Res. 17: 243

    Google Scholar 

  76. Turro NJ (1978) Modern Molecular Photochemistry. Chap 8, Benjamin/Cummings, Menlo Park CA

    Google Scholar 

  77. Ware WR, Holms JD, Arnold DR (1974) J. Am. Chem. Soc. 95: 861

    Google Scholar 

  78. Eberson L, Nyberg K (1966) J. Am. Chem. Soc. 88: 1686

    Google Scholar 

  79. Zweig A, Hodson WG, Jura WH (1964) J. Am. Chem. Soc. 86: 4124

    Google Scholar 

  80. Masuhara H, Mataga N (1981) Acc. Chem. Res. 14: 312

    Google Scholar 

  81. Mattes SL, Farid S (1983) J. Am. Chem. Soc. 195: 1386 J. Am. Chem. Soc. 108: 7356

    Google Scholar 

  82. Mataga N, Shioyama H, Kanda Y (1987) J. Phys. Chem. 91: 314

    Google Scholar 

  83. Gould IR, Moser JE, Ege D, Farid S (1988) J. Am. Chem. Soc. 110: 1991

    Google Scholar 

  84. Eriksen J, Foote CS, Parker TL (1977) J. Am. Chem. Soc. 99: 6455

    Google Scholar 

  85. Orbach N, Ottolenghi M (1975) in: Gordon M, Ware WR (eds) The Exciplex Academic Press, New York, p 75

    Google Scholar 

  86. Schomburg H, Staerk H, Weller A (1973) Chem. Phys. Lett. 22: 1

    Google Scholar 

  87. Mattes SL, Farid S (1980) J. Chem. Soc., Chem. Comm. 126

    Google Scholar 

  88. Saeva FD, Olin GR (1980) J. Am. Chem. Soc. 102: 299

    Google Scholar 

  89. Okada K, Hisanaritsu K, Mukai T (1981) Tetrahedron Lett. 22: 1251

    Google Scholar 

  90. Lopez L, Calò V (1984) J. Chem. Soc., Chem. Comm. 1266

    Google Scholar 

  91. Peover EM (1961) Nature 191: 702

    Google Scholar 

  92. McCullogh JJ, Miller RC, Fung D, Wu WS (1975) J. Am. Chem. Soc. 97: 5942

    Google Scholar 

  93. Chien CK, Wang HC, Szwarc M, Bard AJ, Itaya K (1980) J. Am. Chem. Soc. 102: 3100

    Google Scholar 

  94. Spada LT, Foote CS (1980) J. Am. Chem. Soc. 102: 391

    Google Scholar 

  95. Eriksen J, Foote CS (1980) J. Am. Chem. Soc. 102: 6083

    Google Scholar 

  96. Gollnick K, Schanatterer A (1984) Tetrahedron Lett. 25: 185, and 2735

    Google Scholar 

  97. Ando W, Kabe Y, Takata T (1982) J. Am. Chem. Soc. 104: 7314

    Google Scholar 

  98. Schaap AP, Zaklika KA, Kaskar B, Fung LMW (1980) J. Am. Chem. Soc. 102: 389

    Google Scholar 

  99. Mattes SL, Farid S (1980) J. Chem. Soc., Chem. Comm. 457

    Google Scholar 

  100. Berenjian N, deMayo P, Phoenix FH, Weedon AC (1979) Tetrahedron Lett. 4179

    Google Scholar 

  101. Ando W, Nagashima T, Saito K, Kohmoto S (1979) J. Chem. Soc., Chem. Comm. 154

    Google Scholar 

  102. Schaap AP, Anderson SD, Gagnon SD, Lopez L, Recher SG (1982) IX Symp. on Photochem. Pau (France) Abstract ST 15

    Google Scholar 

  103. Schaap AP, Lopez L, Anderson SD, Gagnon SD (1982) Tetrahedron Lett. 5493

    Google Scholar 

  104. Mizuno K, Kamiyama N, Ichinose N, Otsuji Y (1985) Tetrahedron 41: 2207

    Google Scholar 

  105. Griffin GW, Kirschenheuter GP, Vaz C, Umrigar PP, Lankin DC, Christensen S (1985) Tetrahedron 41: 2069

    Google Scholar 

  106. Brown-Wensley KA, Mattes SL, Farid S (1978) J. Am. Chem. Soc. 100: 4162

    Google Scholar 

  107. Futumara S, Kusunose S, Otha H, Kamiya Y (1984) J. Chem. Soc. Perkin Trans I 15

    Google Scholar 

  108. Schaap AP, Lopez L, Gagnon SD (1983) J. Am. Chem. Soc. 105: 663

    Google Scholar 

  109. Schaap AP, Siddiqui S, Prasad G, Palomino E, Lopez L (1984) J. Photochem. 25: 167

    Google Scholar 

  110. Gollnick K, Schanatterer A (1985) Tetrahedron Lett. 26: 173

    Google Scholar 

  111. Lopez L, Calò V, Aurora R (1986) J. Photochem. 32: 95

    Google Scholar 

  112. Lopez L (1985) Tetrahedron Lett. 26: 4383

    Google Scholar 

  113. Santamaria J, Ouchabane R (1986) Tetrahedron 42: 5559

    Google Scholar 

  114. Santamaria J, Ouchabane R, Rigaudy J (1989) Tetrahedron Lett. 30: 3977

    Google Scholar 

  115. Lopez L, Troisi L, Rashid SMK, Schaap AP (1989) Tetrahedron Lett. 30: 485

    Google Scholar 

  116. Akasaka T, Ando W (1987) J. Am. Chem. Soc. 109: 1260

    Google Scholar 

  117. Kabe Y, Takata T, Ueno K, Ando W (1984) J. Am. Chem. Soc. 106: 8174

    Google Scholar 

  118. Kopecky RK, Mumford C (1969) Can. J. Chem. 47: 709

    Google Scholar 

  119. Foote CS (1985) Tetrahedron 41: 2221

    Google Scholar 

  120. Nelsen SF (1987) Acc. Chem. Res. 20: 269

    Google Scholar 

  121. Clennan EL, Simmons W, Almgreen CW (1981) J. Am. Chem. Soc. 103: 2098

    Google Scholar 

  122. Numan H, Wieringa JH, Wynberg H, Hess J, Vos A (1977) J. Chem. Soc., Chem. Commun. 591

    Google Scholar 

  123. Krebs A, Schmalstieg H, Jarchow O, Klaska KH (1980) Tetrahedron Lett. 21: 3171

    Google Scholar 

  124. Manring LE, Erikson J, Foote CS (1980) J. Am. Chem. Soc. 102: 4275

    Google Scholar 

  125. Barton DHR, Leclerc G, Magnus PD, Menzies ID (1972) J. Chem. Soc., Chem. Commun. 447

    Google Scholar 

  126. Manring LE, Kramer MK, Foote CS (1984) Tetrahedron Lett. 25: 2523

    Google Scholar 

  127. Kwon BM, Foote CS, Khan SI (1989) J. Org. Chem. 54: 3378

    Google Scholar 

  128. Lopez L, Troisi L (1989) Tetrahedron Lett. 30: 485

    Google Scholar 

  129. Mattes SL, Farid S (1982) J. Am. Chem. Soc. 104: 1454

    Google Scholar 

  130. Maroulis AJ, Shigemitsu Y, Arnold DR (1978) J. Am. Chem. Soc. 100: 535

    Google Scholar 

  131. Jiang ZQ, Foote CS (1983) Tetrahedron Lett. 24: 461

    Google Scholar 

  132. Adam W, Arias LA, Zinner K (1983) Chem. Ber. 116: 839

    Google Scholar 

  133. Adam W, Arias LA, Scheutzow D (1982) Tetrahedron Lett. 23: 2835

    Google Scholar 

  134. Nelsen SF, Kapp DL, Teasley MF (1984) J. Org. Chem. 49: 579

    Google Scholar 

  135. Steichen DS, Foote CS (1981) J. Am. Chem. Soc. 103: 1855

    Google Scholar 

  136. Nelsen SF, Teasley MF, Kapp DL (1986) J. Am. Chem. Soc. 108: 5503

    Google Scholar 

  137. Gollnick K, Schnatterer A (1986) Photochem. Photobiol. 43: 365

    Google Scholar 

  138. Barton DHR, Haynes RK, Leclerc G, Magnus PD, Menzies ID (1975) J. Chem. Soc. Perkin Trans. 1: 2055

    Google Scholar 

  139. Haynes RK (1978) Aust. J. Chem. 31: 121, 131

    Google Scholar 

  140. Tang R, Yue HJ, Wolf JF, Mares F (1978) J. Am. Chem. Soc. 100: 5248

    Google Scholar 

  141. Farid S, Brown KA (1976) J. Chem. Soc., Chem. Commun. 564

    Google Scholar 

  142. Lopez L, Troisi L (1989) Tetrahedron Lett. 30: 3097

    Google Scholar 

  143. Delaunay J, Lebouc A, Tallec A, Simonet J (1982) J. Chem. Soc., Chem. Commun. 387

    Google Scholar 

  144. Gill GB, Hands D (1974) Tetrahedron Lett. 181

    Google Scholar 

  145. Haynes RK, Probert MKS, Wilmot ID (1978) Aust. J. Chem. 31: 1737

    Google Scholar 

  146. Curci R, Lopez L, Troisi L, Rashid SMK, Schaap AP (1987) Tetrahedron Lett. 28: 5319

    Google Scholar 

  147. Bell FA, Ledwith A, Sherrington DC (1969) J. Chem. Soc. (C) 2719

    Google Scholar 

  148. Eberson L, Larsson B (1986) Acta Chem. Scand. 40: 210

    Google Scholar 

  149. Belville DJ, Wirth DD, Bauld NL (1981) J. Am. Chem. Soc. 103: 718

    Google Scholar 

  150. Mann CK, Barnes KK (1970) Electrochemical Reactions in Nonaqueous Systems. Dekker, New York

    Google Scholar 

  151. Ouannes C, Wilson (1968) J. Am. Chem. Soc. 90: 6527

    Google Scholar 

  152. Goerner H, Schulte-Frohlinde D (1986) Chem. Phys. Lett. 124: 321

    Google Scholar 

  153. Lopez L, Lacerenza S (1987) XIIIth Int. Conf. of Photochem. Budapest, 9/14 August Abst 2P083

    Google Scholar 

  154. George MV, Kumar CV, Scaiano IC (1979) J. Phys. Chem. 83: 2452

    Google Scholar 

  155. Adam W, Platsch H, Schmidt E (1985) Chem. Ber. 118: 4385

    Google Scholar 

  156. Pagni RM (1984) Tetrahedron 40: 4161

    Google Scholar 

  157. Lopez L, Cal`o V, Stasi F (1987) Synthesis 947

    Google Scholar 

  158. Lopez L, Calò V (1985) Synthesis 774

    Google Scholar 

  159. Ciminale F, Lopez L (1985) Tetrahedron Lett. 26: 789

    Google Scholar 

  160. Schaap AP, Siddiqui S, Gagnon SD, Lopez L (1983) J. Am. Chem. Soc. 105: 5149

    Google Scholar 

  161. Schaap AP, Siddiqui S, Balakrishnan P, Lopez L, Gagnon SD (1983) Isr. J. Chem. 23:415

    Google Scholar 

  162. Schaap AP, Siddiqui S, Prasad G, Palomino E, Sandison M (1985) Tetrahedron 41:2229

    Google Scholar 

  163. Futumara S, Kusunose S, Ohta M, Kamiya Y (1982) J. Chem. Soc., Chem. Commun. 1223

    Google Scholar 

  164. Albini A, Arnold DR (1978) Can. J. Chem. 56: 2985

    Google Scholar 

  165. Griffin GW (1971) Angew. Chem., Int. Ed. Engl. 10: 537

    Google Scholar 

  166. Schaap AP, Siddiqui S, Prasad G, Raham AFM, Oliver JP (1984) J. Am. Chem. Soc. 106: 6087

    Google Scholar 

  167. Farid S, Hartmann SE, Evans TR (1975) in: Gordon M, Ware WR (eds) The Exciplexes. Academic Press, New York, p 327

    Google Scholar 

  168. Mattes SL, Farid S (1982) Acc. Chem. Res. 15: 80

    Google Scholar 

  169. Majima T, Pac C, Sakurai H (1980) J. Am. Chem. Soc. 102: 5265

    Google Scholar 

  170. Majima T, Pac C, Nakasone A, Sakurai H (1981) J. Am. Chem. Soc. 103: 4499

    Google Scholar 

  171. Lee GA (1978) J. Org. Chem. 43: 4256

    Google Scholar 

  172. Huisgen R, Mader H (1969) Angew. Chem., Int. Ed. Engl. 8: 604

    Google Scholar 

  173. Huisgen R, Markowski H (1976) Tetrahedron Lett. 4643

    Google Scholar 

  174. Trozzolo AM, Leslie TM, Sarpotdar AS, Small RD, Ferraudi GJ, Do Minh T, Harless RL (1979) Pure Appl. Chem. 51: 261

    Google Scholar 

  175. Clawson P, Lunn PM, Whiting DA (1984) J. Chem. Soc., Chem. Commun. 134

    Google Scholar 

  176. Wong JPK, Fahmi AA, Griffin GW, Bhacca NS (1981) Tetrahedron 37: 3354

    Google Scholar 

  177. Miyashi T, Kamata M, Mukai T (1986) J. Chem. Soc., Chem. Commun. 1577

    Google Scholar 

  178. Miyashi T, Kamata M, Mukai T (1986) J. Am. Chem. Soc. 108: 2755

    Google Scholar 

  179. Ulmann EF, Henderson Jr WA (1967) J. Am. Chem. Soc. 89: 4390

    Google Scholar 

  180. Saveant JM (1980) Acc. Chem. Res. 113: 19

    Google Scholar 

  181. Schaap AP, Prasad G, Gagnon SD (1983) Tetrahedron Lett. 3047

    Google Scholar 

  182. Schaap AP, Prasad G, Siddiqui S (1984) Tetrahedron Lett. 3035

    Google Scholar 

  183. Sakuragi M, Sakuragi H (1980) Chem. Lett. 1017

    Google Scholar 

  184. Landis M, Madoux DC (1979) J. Am. Chem. Soc. 101: 5106

    Google Scholar 

  185. Akaba R, Aihara S, Sakuragi H, Tokumaru K (1987) J. Chem. Soc., Chem. Commun. 1262

    Google Scholar 

  186. Nicholson RS, Shain I (1964) Anal. Chem. 36: 706

    Google Scholar 

  187. Okada K, Hisamitsu K, Mukai T (1981) Tetrahedron Lett. 22: 1251

    Google Scholar 

  188. Okada K, Hisamitsu K, Miyashi T, Mukai T (1982) J. Chem. Soc., Chem. Commun. 974

    Google Scholar 

  189. Calò V, Lopez L., Pesce G, Todesco PE (1973) Tetrahedron 29: 1625

    Google Scholar 

  190. Calò V, Lopez L, Fiandanese V, Naso F, Ronzini L (1978) Tetrahedron Lett. 4693

    Google Scholar 

  191. Brisimitzakis AC, Schuster DI (1982) Tetrahedron Lett. 23: 4531, 4534

    Google Scholar 

  192. Schuster DI (1978) Accounts Chem. Res. 19: 3329

    Google Scholar 

  193. Lopez L (1987) Conference on Photochem. Como 12/14 Sept. Abst. CO4

    Google Scholar 

  194. Roth HD, Schilling MLM (1979) J. Am. Chem. Soc. 101: 1898

    Google Scholar 

  195. Roth HD, Schilling MLM (1980) J. Am. Chem. Soc. 102: 4303

    Google Scholar 

  196. Roth HD, Schilling MLM (1981) J. Am. Chem. Soc. 103: 7210

    Google Scholar 

  197. Roth HD, Schilling MLM, Jones G (1981) J. Am. Chem. Soc. 103: 1246

    Google Scholar 

  198. Haselbach E, Vauthey E, Suppan P (1988) Tetrahedron 44: 7335

    Google Scholar 

  199. Hilinski EF, Milton SV, Rentzepis PM (1983) J. Am. Chem. Soc. 105: 5196

    Google Scholar 

  200. Foote CS, Burns PA, Mazur S, Lerdal D (1973) J. Am. Chem. Soc. 95: 586

    Google Scholar 

  201. Matsumoto M, Kuroda K (1979) Tetrahedron Lett. 1607

    Google Scholar 

  202. Steichen DS, Foote CS (1979) Tetrahedron Lett. 4363

    Google Scholar 

  203. Eriksen J, Foote CS (1978) J. Phys. Chem. 82: 2654

    Google Scholar 

  204. Manring LE, Gu CI, Foote CS (1983) J. Phys. Chem. 87: 40

    Google Scholar 

  205. Dobrowolski DC, Ogilby PR, Foote CS (1983) J. Phys. Chem. 87: 2261

    Google Scholar 

  206. Ogilby PR, Foote CS (1983) J. Am. Chem. Soc. 105: 3423

    Google Scholar 

  207. Araki Y, Dobrowolski DC, Goyne TE, Hanson DC, Jiang ZQ, Lee KJ, Foote CS (1984) J. Am. Chem. Soc. 106: 4570

    Google Scholar 

  208. Albini A, Spreti S (1985) Gazz. Chim. Ital. 115: 227

    Google Scholar 

  209. Santamaria J (1981) Tetrahedron Lett. 22: 4511

    Google Scholar 

  210. Santamaria J, Gabillet P, Bokobza L (1984) 25: 2139

    Google Scholar 

  211. Van Den Heuvel CJM, Streinberg H, de Boer TJ, Roy J (1980) Neth. Chem. Soc. 99: 109

    Google Scholar 

  212. Rigaudy J, Maumy M (1972) Bull. Soc. Chim. Fr. 3936

    Google Scholar 

  213. Wei SK, Adelman AH (1969) Tetrahedron Lett. 3297

    Google Scholar 

  214. Albini A, Spreti S (1987) J. Chem. Soc. Perkin Trans. II 1175

    Google Scholar 

  215. Saito I, Tamoto K, Matsuura T (1979) Tetrahedron Lett. 2855

    Google Scholar 

  216. Reichel LW, Griffin GW, Muller AJ, Das PK, Ege SN (1984) Can. J. Chem. 62: 424

    Google Scholar 

  217. Davis HF, Das PK, Reichel LW, Griffin GW (1984) J. Am. Chem. Soc. 106: 6968

    Google Scholar 

  218. Fox MA (1987) Top. Curr. Chem. 142: 72

    Google Scholar 

  219. Bard AJ (1982) J. Phys. Chem. 86: 172

    Google Scholar 

  220. Wrighton MS (1979) Acc. Chem. Res. 12: 303

    Google Scholar 

  221. Mozzanega MN, Herrmann JM, Pichat P (1977) Tetrahedron Lett. 2965

    Google Scholar 

  222. Kanno T, Oguchi T, Sakuragi H, Tokumaru K (1980) Tetrahedron Lett. 467

    Google Scholar 

  223. Fox MA, Liding B, Chen CC (1982) J. Am. Chem. Soc. 104: 5828

    Google Scholar 

  224. Fox MA, Chen CC (1983) Tetrahedron Lett. 24: 547

    Google Scholar 

  225. Davidson RS, Pratt JE (1983) Tetrahedron Lett. 24: 5903

    Google Scholar 

  226. Hussein FH, Rudham R (1984) J. Chem. Soc. Faraday Trans. I. 80: 2817

    Google Scholar 

  227. Hirdchwald WH (1985) Acc. Chem. Res. 18: 228

    Google Scholar 

  228. Okamoto K, Yamamoto Y, Tanaka H, Itaya A (1985) Bull. Chem. Soc. Japan 58: 2015

    Google Scholar 

  229. Fox MA, Younathan JN (1986) Tetrahedron 42: 6285

    Google Scholar 

  230. Pavlik JW, Tantayanon S (1981) J. Am. Chem. Soc. 103: 6755

    Google Scholar 

  231. Gerischer H, Willig F (1976) Top. Curr. Chem. 61: 33

    Google Scholar 

  232. Kabir-ud Din, Owen RC, Fox MA (1981) J. Phys. Chem. 85: 1679

    Google Scholar 

  233. Westheimer F (1985) Adv. Phys. Org. Chem. 21: 1

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Centro di Studio sulle Metodologie Innovative di Sintesi Organiche del CNR Dipartimento di Chimica, Università di Bari, via Amendola, 173-70126, Bari, Italy

    Luigi Lopez

Authors
  1. Luigi Lopez
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Jochen Mattay

Rights and permissions

Reprints 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

Publish with us

Policies and ethics

Search

Navigation