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Addition and cycloaddition reactions via photoinduced electron transfer

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 169))

Abstract

This review article deals with addition and cycloaddition reactions of organic compounds via photoinduced electron transfer. Various reactive species such as exciplex, triplex, radical ion pair and free radical ions are generated via photoinduced electron transfer reactions. These reactive species have their characteristic reactivities and discrimination among these species provides selective photoreactions. The solvent and salt effects and also the effects of electron transfer sensitizers on photoinduced electron transfer reactions can be applied to the selective generation of the reactive species. Examples and mechanistic features of photoaddition and photocycloaddition reactions that proceed via the following steps are given: reactions of radical cations with nucleophiles; reactions of radical anions with electrophiles; reactions of radical cations and radical anions with neutral radicals; radical-radical coupling reactions; addition and cycloaddition reactions via triplexes; three-component addition reactions.

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7 References

  1. Chanon M, Hawley MD, Fox MA (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, Part A, Elsevier, Amsterdam, p 1; Chanon M, Eberson L (1988) Ibid, p 409

    Google Scholar 

  2. Roth H (1990) In: Mattay J (ed) Photoinduced electron transfer I, Topics in Current Chemistry, vol 156. Springer, Berlin Heidelberg New York, p 1; Mattay J (1991) In: Mattay J (ed) Photoinduced electron transfer III, Top Curr Chem, vol 159, p 219

    Google Scholar 

  3. Mariano PS, Stavinoha JL (1984) In: Horspool WM (ed) Synthetic organic photochemistry. New York, p 145

    Google Scholar 

  4. Mattes SL, Farid S (1983) Org Photochem 6: 233

    Google Scholar 

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

    Google Scholar 

  6. Chanon M (1985) Bull Soc Chim Fr 209; Chanon M, Rajzmann M, Chanon F (1990) Tetrahedron 46: 6193

    Google Scholar 

  7. Kochi JK (1988) Angew Chem Int Ed Engl 27: 1227

    Article  Google Scholar 

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

    Article  Google Scholar 

  9. Davidson RS (1983) In: Gold V, Bethel D (ed) Advances in Physical organic chemistry, vol 19, Academic, London New York, p 1

    Google Scholar 

  10. Mattay J (1989) Synthesis 233

    Google Scholar 

  11. Beens H, Weller A (1968) Chem Phys Lett 2: 140

    Article  Google Scholar 

  12. Saltiel J, Townsend DE, Watson BD, Shannon P (1975) J Am Chem Soc 97: 5688

    Article  Google Scholar 

  13. Yang NC, Minsek DW, Johnson DG, Larson JR, Petrich JW, Gerald III R, Wasieleski MR (1989) Tetrahedron 45: 4669

    Article  Google Scholar 

  14. Masaki Y, Yanagida S, Pac C (1988) Chem Lett 1305; Masaki Y, Uehara Y, Yanagida S, Pac C (1990) Ibid. 1339; (1992) Ibid. 315

    Google Scholar 

  15. Caldwell RA, Creed D (1978) J Am Chem Soc 100: 2905

    Article  Google Scholar 

  16. Caldwell RA, Creed D (1980) Acc Chem Res 13: 45

    Article  Google Scholar 

  17. Caldwell RA, Creed D, DeMarco DC, Melton LA, Ohta H, Wine PH (1980) J Am Chem Soc 102: 2369

    Article  Google Scholar 

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

    Google Scholar 

  19. Marcus RA (1956) J Chem Phys 24: 966; Marcus RA (1959) Can J Chem 37: 155; Marcus RA (1965) J Chem Phys 43: 58

    Article  Google Scholar 

  20. Gould IR, Young RH, Farid S (1991) In: Honda K (ed) Photochemical processes in organized molecular systems. Elsevier, Amsterdam, p 19; Miller JR (1991) Ibid, p 41

    Google Scholar 

  21. Mataga N (1992) In: Mataga N, Okada T, Masuhara H (eds) Dynamics and mechanisms of photoinduced electron transfer and related phenomena. Elsevier, Amsterdam, p 1; Kakitani T (1992) Ibid, p 71

    Google Scholar 

  22. Mattes SL, Farid S (1986) J Am Chem Soc 108: 7356

    Article  Google Scholar 

  23. Mizuno K, Ichinose N, Otsuji Y (1992) J Org Chem 57: 1855; Mizuno K, Hiromoto Z, Ohnishi K, Otsuji Y (1983) Chem Lett 1059; Ichinose N, Mizuno K, Hiromoto Z, Otsuji Y (1986) Tetrahedron Lett 27: 5619

    Article  Google Scholar 

  24. Santamaria J (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, Part B. Elsevier, Amsterdam, p 483

    Google Scholar 

  25. Pac C, Ishitani O (1988) Photochem Photobio 1988: 47

    Google Scholar 

  26. Loupy A, Tchoubar B, Astruc D (1992) Chem Rev 92: 1141

    Article  Google Scholar 

  27. Mizuno K, Otsuji Y (1988) Yuki Gousei Kagaku Kyoukaishi (J Synth Org Chem Japan) 47: 916

    Google Scholar 

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

    Article  Google Scholar 

  29. Majima T, Pac C, Sakurai H (1981) J Am Chem Soc 103: 4499; Pac C, Nakasone A, Sakurai H (1977) Ibid. 99: 5806

    Article  Google Scholar 

  30. Pac C (1986) Pure & Appl Chem 58: 1249

    Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

  33. Neunteufel RA, Arnold DR (1973) J Am Chem Soc 95: 4080

    Article  Google Scholar 

  34. Shigemitsu Y, Arnold DR (1975) J Chem Soc, Chem Commun 407; Maroulis AJ, Shigemitsu Y, Arnold DR (1978) J Am Chem Soc 100: 535

    Google Scholar 

  35. Maroulis AJ, Arnold DR (1979) Synthesis 819

    Google Scholar 

  36. Maroulis AJ, Arnold DR (1979) J Chem Soc, Chem Commun 351

    Google Scholar 

  37. Mizuno K, Nakanishi I, Ichinose N, Otsuji Y (1989) Chem Lett 1095

    Google Scholar 

  38. Mizuno K, Tamai T, Tani K, Otsuji Y (to be published)

    Google Scholar 

  39. Gassman PG, De Silva SA (1991) J Am Chem Soc 113: 9870

    Article  Google Scholar 

  40. Rao VR, Hixson SS (1979) J Am Chem Soc 101: 6458

    Article  Google Scholar 

  41. Mizuno K, Ogawa J, Otsuji Y (1981) Chem Lett 741

    Google Scholar 

  42. Mazzocchi PH, Somich C, Edwards M, Morgan T, Ammon HL (1986) J Am Chem Soc 108: 682

    Google Scholar 

  43. Ichinose N, Kitamura N, Masuhara H (1991) J Chem Soc, Chem Commun 985; Tomioka H, Inoue O (1988) Bull Chem Soc Jpn 61: 1404

    Google Scholar 

  44. Dinnocenzo JP, Todd WP, Simpson TR, Gould IR (1990) J Am Chem Soc 112: 2462

    Article  Google Scholar 

  45. Gassman PG, Olson KD, Walter L, Yamaguchi R (1981) J Am Chem Soc 103: 4977; Gassman PG, Smith JL (1983) J Org Chem 48: 4438

    Article  Google Scholar 

  46. Gassman PG (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, Part C. Elsevier, Amsterdam, p 70

    Google Scholar 

  47. Mizuno K, Yoshioka K, Otsuji Y (1983) Chem Lett 941

    Google Scholar 

  48. Murai S, Tsutsumi S (1966) Bull Chem Soc Jpn 34: 198

    Google Scholar 

  49. Mizuno K, Ogawa, Kagano, Otsuji Y (1981) Chem Lett 437

    Google Scholar 

  50. Kojima M, Sakuragi H, Tokumaru K (1985) Bull Chem Soc Jpn 58: 521

    Google Scholar 

  51. Asai M, Matsui H, Tazuke S (1974) Bull Chem Soc Jpn 47: 864

    Google Scholar 

  52. Shono T, Matsumura Y (1970) J Org Chem 35: 4157

    Article  Google Scholar 

  53. Mizuno K, Pac C, Sakurai H (1975) J Chem Soc, Chem Commun 553; Yasuda M, Pac C, Sakurai H (1981) J Chem Soc Perkin Trans I 746

    Google Scholar 

  54. Mizuno K, Okamoto H, Pac C, Sakurai H (1975) J Chem Soc, Chem Commun 839; Yasuda M, Pac C, Sakurai H (1981) J Org Chem 46: 788

    Google Scholar 

  55. Cornelisse J, Havinga E (1975) Chem Rev 75: 353

    Article  Google Scholar 

  56. Yasuda M, Yamashita T, Matsumoto T, Shima K, Pac C (1985) J Org Chem 50: 3667

    Article  Google Scholar 

  57. Yasuda M, Yamashita T, Shima K, Pac C (1987) J Org Chem 52: 753

    Article  Google Scholar 

  58. Yasuda M, Shima K (1991) Reviews on Heteroatom Chem 4: 27

    Google Scholar 

  59. Yasuda M, Kubo J, Shima K (1990) Heterocycles 31: 1007; Yasuda M, Hamasuma, Yamano K, Kubo J, Shima K (1992) Heterocycles 34: 965

    Google Scholar 

  60. Pac C, Sakurai H (1969) Tetrahedron Lett 3829; Yasuda M, Pac C, Sakurai H (1981) Bull Chem Soc Jpn 54: 2352

    Google Scholar 

  61. Sugimoto A, Sumida R, Tamai N, Inoue H, Otsuji Y (1981) Bull Chem Soc Jpn 54: 3500; Sugimoto A, Sumi K, Urakawa K, Ikemura M, Sakamoto S, Yoneda S, Otsuji Y (1983) Bull Chem Soc Jpn 56: 3118

    Google Scholar 

  62. Sugimoto A, Yamano J, Suyama K, Yoneda S (1989) J Chem Soc Perkin Trans 1 483; Sugimoto A, Yoneda S (1982) J Chem Soc Chem Commun 376

    Article  Google Scholar 

  63. Sugimoto A, Hiraoka R, Inoue H, Adachi T (1992) J Chem Soc, Perkin Trans, 1, 1559; Sugimoto A, Hiraoka R, Fukada N, Kosaka H, Inoue H (1992) Ibid 1, 2871

    Google Scholar 

  64. Gilbert A (1984) In: Horspool WM (ed) Synthetic organic photochemistry. New York, p 1

    Google Scholar 

  65. Albini A, Sulpizio A (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, Part C. Elsevier, Amsterdam, p 88

    Google Scholar 

  66. Lewis FD, Reddy GD, Schneider S, Gahr M (1989) J Am Chem Soc 111: 6465

    Article  Google Scholar 

  67. Lewis FD, Reddy GD, Schneider S, Gahr M (1991) J Am Chem Soc 113: 3498

    Article  Google Scholar 

  68. Ohashi M, Miyake K, Tsujimoto K (1980) Bull Chem Soc Jpn 53: 1683

    Google Scholar 

  69. Naruto S, Yonemitsu O, Kanamaru N, Kimura K (1971) J Am Chem Soc 93: 4053

    Article  Google Scholar 

  70. Kanaoka Y (1978) Acc Chem Res 11: 407; Sato Y, Nakai H, Mizoguchi T, Hatanaka Y, Kanaoka Y (1976) J Am Chem Soc 98: 1976

    Article  Google Scholar 

  71. Ledwith A (1972) Acc Chem Res 5: 133

    Article  Google Scholar 

  72. Shirota Y, Mikawa H (1978) J Macromol Sci Rev Macromol Chem C16: 129

    Google Scholar 

  73. Shirota Y (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, Part D, Elsevier, Amsterdam, p 441

    Google Scholar 

  74. Kuwata S, Shigemitsu Y, Odaira Y (1972) Chem Commun 2; Kuwata S, Shigemitsu Y, Odaira Y (1973) J Org Chem 38: 3803

    Google Scholar 

  75. Evans TR, Wake RW, Jaenicke O (1975) In: Gordon M, Ware WR (eds) The exciplex. Academic, New York, p 345

    Google Scholar 

  76. Mizuno K, Kagano H, Kasuga T, Otsuji Y (1983) Chem Lett 133; Mizuno K, Otsuji Y (1986) Chem Lett 683

    Google Scholar 

  77. Farid S, Shealer SE (1973) J Chem Soc Chem Commun 677

    Google Scholar 

  78. Yasuda M, Pac C, Sakurai (1980) Bull Chem Soc Jpn 53: 502; Cedheim L, Eberson L (1976) Acta Chem. Scand. B30: 527

    Google Scholar 

  79. Lewis FD, Kojima M (1988) J Am Chem Soc 110: 8664; Kojima M, Sakuragi H, Tokumaru K (1991) Tetrahedron Lett 22: 2889

    Article  Google Scholar 

  80. Asanuma T, Gotoh T, Tsuchida A, Yamamoto M, Nishijima Y (1977) J Chem Soc Chem Commun 485; Yamamoto M, Asanuma T, Nishijima Y (1975) J Chem Soc Chem Commun 53; Asanuma T, Yamamoto M, Nishijima Y (1975) J Chem Soc Chem Commun 56

    Google Scholar 

  81. Mizuno K, Ogawa J, Kamura M, Otsuji Y (1979) Chem Lett 731

    Google Scholar 

  82. Ilyas M, de Mayo P (1985) J Am Chem Soc 107: 5093

    Article  Google Scholar 

  83. Mattes SL, Farid S (1980) J Chem Soc Chem Commun 126

    Google Scholar 

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

    Article  Google Scholar 

  85. Shirota Y, Nishikata A, Aoyama T, Saimatsu J, Oh S-C, Mikawa H (1984) J Chem Soc Chem Commun 64

    Google Scholar 

  86. Yamaguchi K, Oh S-C, Shirota Y (1986) Chem Lett 1445

    Google Scholar 

  87. Mattay J, Trampe G, Runsink J (1988) Chem Ber 121: 1991

    Google Scholar 

  88. Mella M, Fasani E, Albini A (1991) Tetrahedron 47: 3137; Jones CR, Allman BJ, Mooring A, Spahic B (1983) J Am Chem Soc 105: 652

    Article  Google Scholar 

  89. Mizuno K, Kaji R, Otsuji Y (1977) Chem Lett 1027

    Google Scholar 

  90. Farid S, Hartman SE, Evans TR (1975) In: Gordon M, Ware WR (eds) The exciplex. Academic, New York, p 327

    Google Scholar 

  91. Mizuno K, Kaji R, Okada H, Otsuji Y (1978) J Chem Soc, Chem Commun 594

    Google Scholar 

  92. Mizuno K, Ishii M, Otsuji Y (1981) J Am Chem Soc 103: 5570

    Article  Google Scholar 

  93. Mizuno K, Ueda H, Otsuji Y (1981) Chem Lett 1237

    Google Scholar 

  94. Maroulis AJ, Arnold DR (1979) J Chem Soc Chem Commun 351

    Google Scholar 

  95. Arnold DR, Borg RM, Albini A (1981) J Chem Soc Chem Commun 138

    Google Scholar 

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

    Article  Google Scholar 

  97. Bauld NL, Bellville DJ, Pabon PA, Chelsky R, Green G (1983) J Am Chem Soc 105: 2378

    Article  Google Scholar 

  98. Bauld NL, Bellville DJ, Harirchian B, Lorenz KT, Pabon PA, Reynolds DW, Wirth DD, Chion HS, Marsh BK (1987) Acc Chem Res 20: 371

    Article  Google Scholar 

  99. Mizuno K, Hashizume T, Otsuji Y (1983) J Chem Soc, Chem Commun 772

    Google Scholar 

  100. Mella M, Fasani E, Albini A (1992) J Org Chem 57: 6210

    Article  Google Scholar 

  101. Davis HF, Chattopadhyay SK, Das PK (1984) J Phys Chem 88: 2798

    Article  Google Scholar 

  102. Pac C, Ohtsuki S, Yanagida S, Sakurai H (1986) Bull Chem Soc Jpn 59: 1133

    Google Scholar 

  103. Mizuno K, Hashizume T, Otsuji Y (1983) J Chem Soc, Chem Commun 977

    Google Scholar 

  104. Nakanishi K, Mizuno K, Otsuji Y (1991) J Chem Soc, Chem Commun 90

    Google Scholar 

  105. Calhoun GC, Schuster GB (1986) J Am Chem Soc 108: 8021

    Article  Google Scholar 

  106. Wolfle I, Chan S, Schuster GB (1991) J Org Chem 56: 7313

    Article  Google Scholar 

  107. Hartsough D, Schuster GB (1989) J Org Chem 54: 3

    Article  Google Scholar 

  108. Kim J, Schuster GB (1990) J Am Chem Soc 112: 9635

    Article  Google Scholar 

  109. Lopez L (1990) In: Mattay J (ed) Photoinduced electron transfer I, Topics in current chemistry, vol 156. Springer, Berlin Heidelberg, New York

    Google Scholar 

  110. Fox MA (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, Part D. Elsevier, Amsterdam, p 1

    Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

  113. Arnold DR, Maroulis AJ (1977) J Am Chem Soc 99: 7355

    Article  Google Scholar 

  114. Lewis FD (1986) Acc Chem Res 19: 401; Pienta NJ (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, Part C, Elsevier, Amsterdam, p 421

    Article  Google Scholar 

  115. Tomioka H, Miyagawa H (1988) J Chem Soc Chem Commun 1183

    Google Scholar 

  116. Pac C, Ihama M, Yasuda M, Miyauchi Y, Sakurai H (1981) J Am Chem Soc 103: 6495

    Article  Google Scholar 

  117. Ishitani O, Ihama M, Miyauchi Y, Pac C (1985) J Chem Soc, Perkin Trans 1 1527

    Google Scholar 

  118. Pac C, Miyauchi Y, Ishitani O, Ihama M, Yasuda M, Sakurai H (1984) J Org Chem 49: 26

    Article  Google Scholar 

  119. Tazuke S, Ozawa H (1975) J Chem Soc, Chem Commun 273

    Google Scholar 

  120. Toki S, Hida S, Takamuku S, Sakurai H (1984) Nippon Kagaku Kaishi 152

    Google Scholar 

  121. Mizuno K, Ichinose N, Tamai T, Otsuji Y (1985) Tetrahedron Lett 26: 5823

    Article  Google Scholar 

  122. Mizuno K, Tamai T, Nakanishi I, Ichinose N, Otsuji Y (1988) Chem Lett 2065

    Google Scholar 

  123. Tamai T, Mizuno K, Hashida I, Otsuji Y (1991) Photochem Photobiol 54: 23

    Google Scholar 

  124. Mizuno K, Ikeda M, Otsuji Y (1988) Chem Lett 1507; Mizuno K, Nakanishi K, Tachibana A, Otsuji Y (1991) J Chem Soc, Chem Commun 344

    Google Scholar 

  125. Dinnocenzo JP, Farid S, Goodman JL, Gould IR, Todd WP, Mattes SL (1989) J Am Chem Soc 111: 8973; Nakadaira Y, Otani S, Kyushin S, Ohashi M, Sakurai H, Funada Y, Sakamoto K, Sekiguchi A (1991) Chem Lett 601

    Article  Google Scholar 

  126. Viehe HG (1979) Angew Chem Int Ed Engl 18: 917; (1985) Acc Chem Res 18: 148

    Article  Google Scholar 

  127. Mizuno K, Nakanishi K, Chosa J, Nguyen T, Otsuji Y (1989) Tetrahedron Lett 28: 3689

    Article  Google Scholar 

  128. Mizuno K, Nakanishi K, Chosa J, Otsuji Y, to be published

    Google Scholar 

  129. Bruno JW, Marks TJ, Lewis FD (1982) J Am Chem Soc 104: 5579

    Google Scholar 

  130. Pandey G, Soma Sekhar BBV, Bhalerio UT (1990) J Am Chem Soc 112: 5650

    Article  Google Scholar 

  131. Ohga K, Mariano PS (1982) J Am Chem Soc 104: 617

    Article  Google Scholar 

  132. Ohga K, Yoon UC, Mariano PS (1984) J Org Chem 49: 213

    Article  Google Scholar 

  133. Ahmed-Schofield R, Mariano PS (1985) J Org Chem 50: 5667; (1987) Ibid 52: 1478

    Article  Google Scholar 

  134. Mariano PS (1983) Tetrahedron 39: 3485

    Article  Google Scholar 

  135. Mariano PS (1983) Acc Chem Res 16: 130

    Article  Google Scholar 

  136. Yoon UC, Mariano PS (1992) Acc Chem Res 25: 233

    Article  Google Scholar 

  137. Hasegawa E, Xu W, Mariano PS, Yoon UC, Kim JU (1988) J Am Chem Soc 110: 8099; Xu W, Jeon YT, Hasegawa E, Yoon UC, Mariano PS (1989) J Am Chem Soc 111: 413; Xu W, Zhang XM, Mariano PS (1991) J Am Chem Soc 113: 8863

    Article  Google Scholar 

  138. Kubo Y, Imaoka T, Shiragami, Araki T (1986) Chem Lett 1749

    Google Scholar 

  139. Maruyama K, Imahori, Osuka A, Takuwa A, Tagawa H (1986) Chem Lett 1719

    Google Scholar 

  140. Takuwa A, Nishigaichi Y, Yamashita K, Iwamoto H (1990) Chem Lett 639; Takuwa A, Nishigaichi Y, Iwamoto H (1991) Ibid 1013

    Google Scholar 

  141. Cohen SG, Parola A, Parsons Jr GH (1973) Chem Rev 73: 141

    Article  Google Scholar 

  142. Pac C, Sakurai H, Tosa T (1970) Chem Commun 1311

    Google Scholar 

  143. Pac C, Mizuno K, Tosa T, Sakurai H (1974) J Chem Soc Perkin I 561

    Google Scholar 

  144. Mizuno K, Ikeda M, Otsuji Y (1985) Tetrahedron Lett 26: 461; Mizuno K, Nakanishi K, Otsuji Y (1988) Chem Lett 1833; Mizuno K, Kobata T, Maeda R, Otsuji Y (1990) Ibid 1821

    Article  Google Scholar 

  145. Mizuno K, Toda S, Otsuji Y (1987) Chem Lett 203; (1987) Nippon Kagaku Kaishi 1183

    Google Scholar 

  146. Mizuno K, Terasaka K, Ikeda M, Otsuji Y (1985) Tetrahedron Lett 26: 5819; Mizuno K, Terasaka K, Yasueda M, Otusji Y (1988) Chem Lett 145; Mizuno K, Nishiyama T, Terasaka K, Yasuda M, Shima K, Otsuji Y (1992) Tetrahedron (in press)

    Article  Google Scholar 

  147. Eaton DF (1980) J Am Chem Soc 102: 328; (1981) J Am Chem Soc 103: 7235

    Article  Google Scholar 

  148. Mella M, Fasani E, Albini A (1992) J Photochem Photobiol A: Chem 65: 383; (1992) J Org Chem 57: 6210

    Article  Google Scholar 

  149. Lan JY, Schuster GB (1985) J Am Chem Soc 107: 6710; (1986) Tetrahedron Lett 4261

    Article  Google Scholar 

  150. Kyushin S, Ehara Y, Nakadaira Y, Ohashi M (1989) J Chem Soc Chem Commun 279; Kyushin S, Nakadaira Y, Ohashi M (1990) Chem Lett 2191; Kyushin S, Masuda Y, Matsushita K, Nakadaira Y, Ohashi M (1990) Tetrahedron Lett 31: 6395

    Google Scholar 

  151. Fukuzumi S, Kuroda S, Tanaka T (1986) J Chem Soc Chem Commun 1553; Fukuzumi S, Kitano T, Mochida K (1989) Chem Lett 2177

    Google Scholar 

  152. Mattes SL, Farid S (1986) J Am Chem Soc 108: 7356

    Article  Google Scholar 

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

    Article  Google Scholar 

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

    Google Scholar 

  155. Tamai T, Mizuno K, Hashida I, Otsuji Y (1993) Tetrahedron Lett 34: 2641

    Google Scholar 

  156. Mizuno K, Murakami K, Kamiyama N, Otsuji Y (1983) J Chem Soc Chem Commun 462

    Google Scholar 

  157. Mizuno K, Kamiyama N, Ichinose N, Otsuji Y (1985) Tetrahedron 41: 2207; Mizuno K, Kamiyama N, Otsuji Y (1983) Chem Lett 477

    Article  Google Scholar 

  158. Tamai T, Mizuno K, Hashida I, Otsuji Y (1992) J Org Chem 57: 5338

    Google Scholar 

  159. Ichinose N, Mizuno K, Tamai T, Otsuji Y (1990) J Org Chem 55: 4079

    Google Scholar 

  160. Shim SC, Song JS (1986) J Org Chem 51: 2817

    Google Scholar 

  161. Takahashi Y, Miyashi T, Mukai T (1983) J Am Chem Soc 105: 6511; Miyashi T, Takahashi Y, Mukai T, Roth HD, Schilling MLM (1985) Ibid 107: 1079

    Google Scholar 

  162. Miyashi T, Kamata M, Mukai T (1986) J Chem Soc Chem Commun 1577; Miyashi T, Kamata M, Mukai T (1987) J Am Chem Soc 109: 2780

    Google Scholar 

  163. Tomioka H, Kobayashi D, Hashimoto A, Murata S (1989) Tetrahedron Lett 30: 4685

    Google Scholar 

  164. Miyashi T, Konno A, Takahashi Y (1988) J Am Chem Soc 110: 3676; Miyashi T, Ikeda H, Konno A, Okitsu O, Takahashi Y (1990) Pure & Appl Chem 62: 1531

    Google Scholar 

  165. Schaap AP, Siddiqui S, Gagnon SD, Prasad G, Palmono E, Lopez L (1984) J Photochem 25: 167; Schaap AP, Prasad G, Siddiqui S (1984) Tetrahedron Lett 25: 3035

    Google Scholar 

  166. Akasaka T, Sato K, Kako M, Ando W (1991) Tetrahedron Lett 32: 6605

    Google Scholar 

  167. Mizuno K, Ichinose N, Tamai T, Otsuji Y (1992) J Org Chem 57: 4669; Ichinose N, Mizuno K, Yoshida K, Otsuji Y (1988) Chem Lett 723

    Google Scholar 

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

    Google Scholar 

  169. Muller F, Mattey J (1991) Angew Chem Int Ed Engl 30: 1336

    Google Scholar 

  170. Kamata M, Miyashi T (1989) J Chem Soc Chem Commun 557

    Google Scholar 

  171. McCullough JJ, Wu WS (1972) J Chem Soc Chem Commun 1136; McCullough JJ, Miller RC, Fung D, Wu WS (1975) J Am Chem Soc 97: 5942; McCullough JJ, Miller RC, Wu W-S (1977) Can J Chem 55: 2909

    Google Scholar 

  172. Mizuno K, Pac C, Sakurai H (1974) J Am Chem Soc 96: 2993

    Google Scholar 

  173. Lewis FD, DeVoe RJ, MacBlane DB (1982) J Org Chem 47: 1392

    Google Scholar 

  174. Lewis FD, DeVoe RJ (1982) Tetrahedron 38: 1069

    Google Scholar 

  175. Borg RM, Arnold DR, Cameron TS (1984) Can J Chem 62: 1785; Arnold DR, Snow MS (1988) Can J Chem 66: 3012; Arnold Dr, Du X (1989) J Am Chem Soc 111: 7666

    Google Scholar 

  176. Kubo Y, Suto M, Araki T, Mazzocchi PH, Klingler L, Shook D, Somich C (1986) J Org Chem 51: 4404; Maruyama K, Kubo Y (1985) Ibid 50: 1426; Maruyama K, Kubo Y, Machida M, Oda K, Kanaoka Y, Fukuyama K (1978) Ibid 43: 2303

    Google Scholar 

  177. Mariano PS, Stavinoha JL, Pepe G, Meyer EF (1978) J Am Chem Soc 100: 7114

    Google Scholar 

  178. Mazzocchi PH, Minamikawa S, Wilson P (1985) J Org Chem 50: 2681

    Google Scholar 

  179. Yamada S, Kimura Y, Ohashi M (1977) J Chem Soc Chem Commun 667

    Google Scholar 

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Mizuno, K., Otsuji, Y. (1994). Addition and cycloaddition reactions via photoinduced electron transfer. In: Mattay, J. (eds) Electron Transfer I. Topics in Current Chemistry, vol 169. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-57565-0_79

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  • DOI: https://doi.org/10.1007/3-540-57565-0_79

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  • Publisher Name: Springer, Berlin, Heidelberg

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  • Online ISBN: 978-3-540-48225-3

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