Novel Organic Syntheses Through Semiconductor Photocatalysis

Electron Transfer in Chemistry

Volumn 4, Issue , 2008, Pages 232-278

  Kisch, Horst ^a   Hopfner, Matthias ^a  

^a Institut für Anorganische Chemie   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC SYNTHESIS; SEMICONDUCTOR PHOTOCATALYSIS;

EID: 84955347778     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527618248.ch52     Document Type: Chapter

References (229)

1. V. Carassiti, EPA Newsl. 1984, 21, 12
2. H. Kisch, H. Pfennig, EPA Newsl. 1983, 19, 23
3. A. Albini, J. Chem. Educ. 1986, 63, 383.
4. H. Hennig, D. Rehorek, R. D. Archer, Coord. Chem. Rev. 1985, 61, 1.
5. C. Kutal, Coord. Chem. Rev. 1985, 64, 191.
6. L. Moggi, A. Juris, D. Sandrini, M. F. Manfrin, Res. Chem. Intermed. 1981, 4, 171.
7. J. Plotnikov, Allgemeine Photochemie, Walter de Gruyter, Berlin, 1936, p. 362.
8. R. G. Salomon, Tetrahedron 1983, 39. 485.
9. S. J. Teichner, M. Formenti, in Photoelectrochemistry, Photocatalysis and Photoreactors (Ed. M. Schiavello), Reidel, Dordrecht, 1985, p. 457.
10. M. S. Wrighton, D. S. Ginley, M. A. Schroeder, D. L. Morse, Pure Appl. Chem. 1975, 41, 671.
11. G. G. Wubbels, Acc. Chem. Res. 1983, 16, 285.
12. As defined in 'Glossary of Terms used in Photochemistry', EPA Newsl. 1985, 25, 13.
13. V. Balzani, F. Boletta, M. Ciano, M. Maestri, J. Chem. Educ. 1983, 60, 447.
14. A. J. Bard, J. Photochem. 1979, 10, 59.
15. M. Boudart, G. Djega-Mariadassou, Kinetics of Heterogeneous Catalytic Reactions, Princeton University Press, Princeton, NJ, 1984, p. 6.
16. F. Basolo, R. G. Pearson, Mechanism of Inorganic Reactions, Wiley, New York, 1967.
17. S. G. Davies, Organotransition Metal Chemistry: Applications to Organic Synthesis, Pergamon Press, Oxford, 1982.
18. It was proposed to take the number of molecules present in one monolayer, about 1014 per cm2, as an estimate [17].
19. L. P. Childs, D. F. Ollis, J. Catal. 1980, 66, 383.
20. G. N. Schrauzer, T. D. Guth, J. Am. Chem. Soc. 1977, 99, 7189.
21. H. Gerischer, in Physical Chemistry, Vol. 9A (Eds. M. Eyring, D. Henderson, W. Jost), Academic Press, New York, 1970, p. 463.
22. S. N. Frank, A. J. Bard. J. Am. Chem. Soc. 1977, 99, 4667.
23. S. N. Frank, A. J. Bard, J. Am. Chem. Soc. 1977, 99, 303.
24. S. N. Frank, A. J. Bard, J. Phys. Chem. 1977, 81, 1484.
25. B. Kraeutler, A. J. Bard, J. Am. Chem. Soc. 1977, 99, 7729.
26. A. J. Nozik, R. Memming, J. Phys. Chem. 1996, 100, 13061.
27. M. A. Fox, Top. Curr. Chem. 1987, 142, 71.
28. A. Henglein, Top. Curr. Chem. 1988, 143, 113.
29. N. Serpone, E. Pelizzetti, Photocatalysis, Wiley, New York, 1989.
30. J. G. Edwards, J.-A. Davies, D. L. Boucher, A. Mennad, Angew. Chem. 1992, 104, 489.
31. W. Hetterich, H. Kisch, Chem. Ber. 1989, 122, 621.
32. H. Reiche, A. J. Bard, J. Am. Chem. Soc. 1979, 101, 3127
33. J. Onoe, T. Kawai, S. Kawai, Chem. Lett. 1985, 1667.
34. A. Heller, Y. Degani, D. W. Johnson, P. K. Gallagher, J. Phys. Chem. 1987, 91, 43.
35. A. Fujishima, K. Hashimoto, T. Watanabe, TiO2 Photocatalysis, Fundamentals and Applications, Koyo Printing, Tokyo, 1999.
36. P. V. Kamat, Chem. Rev. 1993, 93, 267.
37. R. Memming, Top. Curr. Chem. 1988, 149, 137.
38. H. Tributsch, in Ref. [27], Chap. 11.
39. B. Kraeutler, A. J. Bard, J. Am. Chem. Soc. 1978, 100, 59-85.
40. H. Gerischer, J. Phys. Chem. 1984, 88, 60-96.
41. D. E. Aspnes, A. Heller, J. Phys. Chem. 1983, 67, 49-19.
42. A. J. Bard, Science 1980, 207, 172.
43. G. Hodes, in Energy Resources Through Photochemistry and Catalysis (Ed. M. Grätzel), Academic Press, New York, 1983, p. 421.
44. G. Rothenberger, J. Moser, M. Grätzel, N. Serpone, D. K. Sharma, J. Am. Chem. Soc. 1985, 107, 80-94.
45. P. V. Kamat, T. W. Ebbesen, N. M. Dimitrijevic, A. J. Nozik, Chem. Phys. Lett. 1989, 157, 384.
46. G. Hodes, J. Electrochem. Soc. 1992, 139, 3136.
47. A. Wahl, J. Augustynski, J. Phys. Chem. B 1998, 102, 7820.
48. W. Schindler, H. Kisch, J. Photochem. Photobiol. A: Chem. 1997, 103, 257.
49. J. Cunningham, S. Srijaranai. J. Photochem. Photobiol. A: Chem. 1991, 58, 361
50. J. Cunningham, G. Al-Sayyed, P. Sedlak, J. Caffrey, Catal. Today, 1999, 53, 145.
51. C. Anderson, A. J. Bard, J. Phys. Chem. B 1997, 101, 2611.
52. C. Anderson, A. J. Bard, J. Phys. Chem. 1995, 99, 9882.
53. The redox potential may change by almost 1 V when one form of the redox couple is adsorbed much more strongly than the other; see Ref. [50].
54. J. F. Rodriguez, J. E. Harris, M. E. Bothwell, Th. Mebrahtu, M. P. Soriaga, Inorg. Chim. Acta 1988, 148, 123.
55. F.-R. F. Fan, P. Leempoel, A. J. Bard, J. Electrochem. Soc. 1983, 130, 18-66.
56. J. R. White, A. J. Bard, J. Phys. Chem. 1985, 89, 19-47.
57. J. R. White, A. J. Bard, J. Am. Chem. Soc. 1985, 105, 27.
58. H. Tributsch, J. C. Bennett, J. Chem. Tech. Biotechnol. 1981, 31, 565.
59. M. F. Finlayson, B. L. Wheeler, N. Kakuta, K.-H. Park, A. J. Bard, A. Campion, M. A. Fox, S. E. Webber, J. M. White, J. Phys. Chem. 1985, 89, 56-76.
60. D. Meissner, R. Memming, B. Kastening, J. Phys. Chem. 1988, 92, 34-76.
61. M. J. Natan, J. W. Thackeray, M. S. Wrighton, J. Phys. Chem. 1986, 90, 40-89.
62. G. Redmond, D. Fitzmaurice, J. Phys. Chem. 1993, 97, 14-26.
63. H. Harada, T. Sakata, T. Ueda, J. Am. Chem. Soc. 1985, 107, 17-73.
64. T. Shiragami, C. Pac, S. Yanagida, J. Chem. Soc., Chem. Commun. 1989, 831.
65. N. Serpone, R. Terzian, D. Lawless, P. Kennepohl, G. Sauvé, J. Photochem. Photobiol. A: Chem. 1993, 73, 11.
66. M. Schiavello, V. Augugliaro, L. Palmisano, J. Catal. 1991, 127, 332.
67. L. Sun, J. R. Bolton, J. Phys. Chem. 1996, 100, 4127.
68. for details see Ref. [66] and H. Kisch, J. Prakt. Chem. 1994, 336, 635.
69. A typical value for a given set-up is ≥1015 photons s-1.
70. T. A. Egerton, C. J. King, J. Oil Colour Chem. Assoc. 1979, 62, 386.
71. S. Sato, J. Phys. Chem. 1983, 87, 3531.
72. H. Al-Ekabi, P. de Mayo, J. Phys. Chem. 1985, 89, 5815.
73. R. Rosetti, L. Brus, J. Phys. Chem. 1982, 86, 44-70.
74. G. Y. Myer, L. K. Leung, J. C. Yu, G. C. Lisensky, A. B. Ellis, J. Am. Chem. Soc. 1989, 111, 5146.
75. T. Uchihara, M. Matsumara, H. Tsubomura, J. Phys. Chem. 1989, 93, 3207.
76. M. Anpo, A. Matsumoto, S. Kodama, J. Chem. Soc., Chem. Commun. 1987, 10-38.
77. A. M. Draper, M. Ilyas, P. de Mayo, V. Ramamurthy, J. Am. Chem. Soc. 1984, 106, 6222.
78. J. M. Herrmann, H. Courbon, P. Pichat, J. Catal. 1985, 95, 539.
79. F. H. Hussein, R. Rudham, J. Chem. Soc., Faraday Trans. 1 1987, 83, 16-31.
80. L. V. Lyashenko, Y. B. Gorokhovatski, V. I. Stepanenko, F. A. Yamposkaya, Teor. Eksp. Khim. 1976, 93, 35.
81. P. Pichat, M. N. Mozzanega, J. Disdier, J. M. Herrmann, Nouv. J. Chim. 1982, 6, 559.
82. P. Pichat, J. M. Herrmann, in Ref. [27], Chap. 1.
83. A. Mills, R. Davies, J. Photochem. Photobiol. A: Chem. 1995, 85, 173.
84. H. Al-Ekabi, P. de Mayo, Tetrahedron 1986, 43, 6277.
85. A. Heller, Y. Degani, D. W. Johnson, P. K. Gallagher, J. Phys. Chem. 1987, 91, 5987.
86. J. F. Reber, M. Rusek, J. Phys. Chem. 1986, 90, 824.
87. Note that only for nonporous materials the surface area increases with smaller particle size; however, most of the powders employed are very porous.
88. B. R. Müller, S. Majoni, R. Memming, D. Meissner, J. Phys. Chem. B. 1997, 101, 2501.
89. P. Lenard, Ann. Phys. 1922, 68, 553.
90. H. P. Weiser, A. D. Garrison, J. Phys. Chem. 1927, 31, 12-37.
91. H. Platz, P. W. Schenk, Angew. Chem. 1936, 49, 822.
92. J. J. Hopfield, J. Phys. Chem. Solids 1959, 10, 110.
93. J. L. Birman, C. Shakin, Phys. Rev. 1958, 109, 810.
94. J. L. Birman, Phys. Rev. 1959, 115, 14-93.
95. M. Cardona, Phys. Chem. Solids 1963, 24, 15-43.
96. M. Cardona, G. Harbeke, Phys. Rev. 1965, 137, 14-67.
97. S. Yanagida, K. Mizumoto, C. Pac, J. Am. Chem. Soc. 1986, 108, 647.
98. S. Yanagida, Y. Ishimura, Y. Miyake, T. Shiragami, C. Pac, K. Hashimoto, T. Sakata, J. Phys. Chem. 1989, 93, 25-76.
99. S. Baral, A. Fojtik, H. Weller, A. Henglein, J. Am. Chem. Soc. 1986, 108, 375.
100. A. Kurian, C. V. Suryanarayana, J. Appl. Electrochem. 1972, 2, 223.
101. R. Künneth, G. Twardzik, G. Emig, H. Kisch, J. Photochem. Photobiol. A: Chem. 1993. 76, 209.
102. H. Kisch, J. Bücheler, Bull. Chem. Soc. Jpn. 1990, 63, 23-78.
103. M. Anpo, S. C. Moon, K. Chiba, G. Martras, S. Coluccia, Res. Chem. Intermed. 1993, 19, 495.
104. M. Anpo, Surface Photochemistry, Vol. 1, Wiley, New York, 1996.
105. G. Hörner, H. Kisch, unpublished work.
106. G. Hörner, A. Fernandez, H. Kisch, unpublished work.
107. These bands are known as 'self-activated luminescence' [104].
108. A. S. Marfunin, Spectroscopy, Luminescence and Radiation Centers in Minerals, Springer, Berlin, 1979, p. 176.
109. K. Sooklal, B. S. Cullum, S. M. Angel, C. J. Murphy, J. Phys. Chem. 1996, 100, 45-51.
110. L. Spanhel, M. Haase, H. Weller, A. Henglein, J. Am. Chem. Soc. 1987, 109, 5649.
111. A. Henglein, Ber. Bunsenges. Phys. Chem. 1982, 86, 301.
112. G. Hörner, P. Johne, R. Künneth, G. Twardzik, H. Roth, T. Clark, H. Kisch, Chem. Eur. J. 1999, 5, 208.
113. S. Yanagida, H. Kawakami, K. Hashimoto, T. Sakata, C. Pac, H. Sakurai, Chem. Lett. 1984, 14-49.
114. W. J. Albery, P. N. Bartlett, C. P. Wilde, J. D. Darwent, J. Am. Chem. Soc. 1985. 107, 18-54.
115. W. J. Albery, G. T. Brown, J. R. Darwent, E. Saievar-Iranizad, J. Chem. Soc. Faraday Trans. 1 1985, 81, 19-99.
116. D. R. James, Y. S. Liu, P. d. Mayo, W. R. Ware, Chem. Phys. Lett. 1985, 120, 460.
117. A. Reinheimer, A. Fernandez, H. Kisch, Z. Phys. Chem. 1999, 213 II, 129.
118. A. M. Roy, G. C. De, N. Sasmal, S. S. Bhattacharyya, Int. J. Hydrogen Energy 1995, 20, 627.
119. H. Weiss, Master Thesis, University of Erlangen 1999.
120. In the literature, the expression 'photocatalysis' is often used in a misleading manner because in most cases it means that for a reaction the presence of a semiconductor is essential; however, it has been proven only in a few cases that the formation of products is catalytic; see H. Kisch, J. Prakt. Chem. 1994, 336, 635.
121. M. Anpo, M. Yabuta, S. Kodama, Y. Kubokawa, Bull. Chem. Soc. Jpn. 1986, 59, 259.
122. S. Kodama, N. Nakaya, M. Anpo, Y. Kubokawa, Chem. Bull. Chem. Soc. Jpn. 1985, 58, 3645.
123. S. Kodama, S. Yagi, J. Phys. Chem. 1998, 93, 4556.
124. M. Anpo, M. Sunamoto, J. Phys. Chem. 1989, 93, 1187.
125. H. Ikezawa, C. Kutal, J. Org. Chem. 1987, 52, 3299.
126. H. Al-Ekabi, P. de Mayo, J. Phys. Chem. 1986, 90, 4075.
127. A. Maldotti, R. Amadelli, C. Martocci, V. Carassiti, Photochem. Photobiol. A: Chem. 1990, 53, 263.
128. C. M. Wang, T. E. Mallouk, J. Am. Chem. Soc. 1990, 112, 2016.
129. R. Barber, P. de Mayo, K. Okada, J. Chem. Soc., Chem. Commun. 1982, 106, 1073.
130. M. Ilyas, P. de Mayo, J. Am. Chem. Soc. 1985, 107, 5093.
131. M. A. Fox, T. Pettit, J. Org. Chem. 1985, 50, 5013.
132. P. Boarini, V. Carassiti, A. Maldotti, R. Amadelli, Langmuir 1998, 14, 2080.
133. C. Joyce-Pruden, J. K. Pross, Y. Li, J. Org. Chem. 1992, 57, 5087.
134. F. Mahdavi, T. C. Bruton, Y. Li, J. Org. Chem. 1993, 58, 744.
135. B. Ohtani, H. Osaki, S. Nishimoto, T. Kagiya, J. Am. Chem. Soc. 1986. 108, 308.
136. M. Schmittel, A. Burghard, Angew. Chem., Int. Ed. Engl. 1997, 36, 2551.
137. T. Linker, M. Schmittel, Radikale und Radikalionen in der Organischen Synthese, Wiley-VCH. Weinheim, 1998.
138. T. Takizawa, T. Watanabe, K. Honda, J. Phys. Chem. 1977, 81, 1845.
139. T. Takizawa, T. Watanabe, K. Honda, J. Phys. Chem. 1978, 82, 1391.
140. Here and in the following the use of the chemical formula indicates that the semiconductor was present as a powder suspension.
141. B. Ohtani, S. Kusakabe, S. Nishimoto, M. Matsumura, Y. Nakato, Chem. Lett. 1995, 803.
142. B. Ohtani, S. Kusakabe, S. Nishimoto, K. Okada, S. Tsuru, K. Izawa, Y. Amino, Tetrahedron Lett. 1995, 36, 3189.
143. K. H. Park, K. Jun, Bull. Korean Chem. Soc. 1998, 19, 919.
144. L. Cermenati, C. Richter, A. Albini, J. Chem. Soc., Chem. Commun. 1998, 805.
145. L. Cermenati, M. Mella, A. Albini, Tetrahedron 1998, 54, 2575.
146. R. Künneth, C. Feldmer, H. Kisch, Angew. Chem. 1992, 104, 1102.
147. R. Künneth, C. Feldmer, H. Kisch, Chem. Eur. J. 1995, 1, 441.
148. J. Bücheler, N. Zeug, H. Kisch, Angew. Chem. 1982, 94, 792.
149. W. Hetterich, H. Kisch, J. Photochem. Photobiol. 1988, 121, 15.
150. N. Zeug, J. Bücheler, H. Kisch, J. Am. Chem. Soc. 1985, 107, 1459.
151. An often neglected aspect in many 'sacrificial' systems of water splitting, i.e., hydrogen evolution can only be observed after adding a reducing agent.
152. S. Yanagida, T. Azuma, Y. Midori, C. Pac, H. Sakurai, J. Chem. Soc., Perkin Trans. 2 1985, 1487
153. S. Yanagida, H. Kawakami, Y. Midori, H. Kizumoto, C. Pac, Y. Wada, Bull. Chem. Soc. Jpn. 1995, 68, 1811.
154. G. Hörner, H. Kisch, unpublished results.
155. A. W. Adamson, Physical Chemistry of Surfaces, 4th edn, Wiley, New York, 1982
156. P.C. Hiemenz, Principles of Colloid and Surface Chemistry, 2nd edn. Marcel Dekker, New York, 1986.
157. Estimated according to 3.8 × 2.4 Å.
158. Q. Zhang, Z. Xu, J. A. Finch, J. Colloid Interface Sci. 1995, 169, 414
159. assuming that each zinc site is occupied by one 2,5-DHF molecule.
160. Although the lifetime of the reactive electron-hole pair is not known, the reasonable estimate of 10-6-10-9 s leads to an electron transfer rate constant between 1010 and 1013 M-1 s-1. In general, electron transfer reactions at the semiconductor-liquid interface are very fast [see Ref. [33] and N. Serpone, E. Pellizetti (Eds.), Homogeneous and Heterogeneous Photocatalysis, Reidel, Dordrecht, 1986, p. 51].
161. A. Henglein, M. Gutierrez, C.-H. Fischer, Ber. Bunsenges. Phys. Chem. 1984, 88, 170.
162. S. Kodama, A. Matsumoto, Y. Kubokawa, M. Anpo, Bull. Chem. Soc. Jpn. 1986, 59, 3765.
163. Y. Nakaoka, Y. Nosaka, Langmuir 1997, 13, 708.
164. L. Lunazzi, G. Placucci, L. Grossi, Tetrahedron 1983, 39, 159.
165. M. Bruening, E. Moons, D. Yaron-Marcovic, D. Cahen, J. Libman, A. Shanzer, J. Am. Chem. Soc. 1994, 116, 2972.
166. M. Bruening, E. Moons, D. Cahen, A. Shanzer, J. Phys. Chem. 1995, 99, 8368.
167. M. Bruening, R. Cohen, J. F. Guillemoles, T. Moav, J. Libman, A. Shanzer, D. Cahen, J. Am. Chem. Soc. 1997, 119, 5720.
168. Calculated by using E0(H+/H) = -2.40 V (H2O) [161] and a bond dissociation energy of 3.22 eV [106]; these were converted to the δG(H2O) values by substracting 0.1 eV for the solvent contribution [161]. The same argument was used to explain the photooxidation of alcohols by ZnS [153].
169. V. D. Parker, J. Am. Chem. Soc. 1992, 114, 7458.
170. F. Wilkinson, Chemical Kinetics and Reaction Mechanism, Van Nostrand Reinhold Co., Wokingham, 1980.
171. It is noted that deuterium is not incorporated into unreacted 2,5-DHF and dehydrodimers when D2O is employed [145].
172. A. Reinheimer, R. v. Eldik, H. Kisch, J. Phys. Chem. B 2000, 104, 1014.
173. A. Fojtik, H. Weller, U. Knoch, A. Henglein, Ber. Bunsenges. Phys. Chem. 1984, 89, 969.
174. G. O. Schenk, H. Formanek, Angew. Chem. 1958, 70, 505.
175. R. C. Cookson, I. D. R. Stevens, C. T. Watts, J. Chem. Soc., Chem. Commun. 1965, 259.
176. G. Ahlgren, Tetrahedron Lett. 1974, 2779.
177. R. Askani, Chem. Ber. 1965, 98, 2551.
178. I. Rosenthal, D. Elad, Tetrahedron 1967, 23, 3193.
179. G. Ahlgren, J. Org. Chem. 1973, 38, 1369.
180. I. Ninomiya, T. Naito, Photochemical Synthesis, Academic Press, New York, 1989.
181. B. H. Al-Sader, R. J. Crawford, Can. J. Chem. 1970, 48, 2745.
182. D. Chan, J. W. Perram, L. R. White, T. W. Healy, J. Chem. Soc., Faraday Trans. 1 1975, 1046.
183. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim, 1988, p. 364.
184. From comparison with the dipole moments of THF, 2,5-DHF and furan (1.63, 1.59 and 0.66 D, respectively) one would expect, however, that the ETN value of 2,5-DHF should be in the range 0.164-0.27, corresponding to furan and THF, respectively;
185. D. R. Lide, H. P. R. Raton (Eds.), Handbook of Chemistry and Physics, 75th edn, CRC Press, Boca Raton, FL, 1994.
186. Estimated from a molecular model as 4.6 × 4.5 Å.
187. Estimated from a molecular model as 10.8 × 4.8 Å.
188. Since light could not be completely excluded in the dark adsorption experiments, cis-azobenzene was present at about 1 %.
189. S. W. Park, C. P. Huang, J. Colloid Interface Sci. 1987, 117, 431.
190. T. J. Bandosz, C. Lin, J. A. Ritter, J. Colloid Interface Sci. 1998, 198, 347.
191. A. Reinheimer, H. Kisch, unpublished work.
192. Φapp of 1,2-diphenyldiazene was set to 1.0.
193. A. J. Bard, W. Lund, Encyclopedia of Electrochemistry of the Elements, Organic Section, Marcel Dekker, New York, 1978.
194. R. Sustmann, R. Sauer, J. Chem. Soc., Chem. Commun. 1985, 1248.
195. P. S. Engel, W.-X. Wu, J. Am. Chem. Soc. 1989, 111, 1831, 5506.
196. C. Lagercranz, J. Deinum, Acta Chem. Scand. 1984, 48, 670.
197. This was observed in the system benzaldehyde-3,4-DHP; A. G. Griesbeck, S. Stadtmüller, J. Am. Chem. Soc. 1989, 111, 1830.
198. An alternative mechanism could involve addition of the dihydropyranyl radical to the diazene and subsequent H-abstraction from 3,4-DHP to produce the product 13a and a new dihy-dropyranylradical. The latter should induce a radical chain reaction, the presence of which lacks any experimental evidence.
199. S. Hashimoto, K. Kano, Bull. Chem. Soc. Jpn. 1972, 45, 852.
200. L. Flamingi, S. Monti, J. Phys. Chem. 1985. 89, 3702.
201. P. Neta, H. Levanon, J. Phys. Chem. 1977, 81, 2288.
202. J. Griffiths, Chem. Soc. Rev. 1972, 1, 481.
203. R. H. Poirier, E. J. Kahler, F. Benington, J. Org. Chem. 1952, 17, 1437.
204. K. Yoshida, T. Kanbe, T. Fueno, J. Org. Chem. 1977, 42, 2313.
205. K. Schäfer, Landolt-Börnstein, Zahlenwerte und Funktionen, Vol. 6, Bd. II/5a, Springer, Berlin, 1969.
206. K. R. Srinivasan, R. L. Kay, J. Solution Chem. 1977, 6, 357.
207. D. W. Brazier, G. R. Freeman, Can. J. Chem. 1969, 47, 893.
208. M. G. Gonikberg, Chemical Equilibria and Reaction Rates at High Pressure, Israel Program for Scientific Translations, Jerusalem, 1963.
209. M. Miyahara, S. Iwasaki, T. Kotera, T. Kawamura, M. Okazaki, J. Colloid Interface Sci. 1995, 170, 335.
210. M. E. Williams, J. C. Crooker, R. Pyati, L. J. Lyons, R. W. Murray, J. Am. Chem. Soc. 1997. 119, 10249.
211. O. S. Anderson, S. W. Feldberg, J. Phys. Chem. 1996, 100, 4622.
212. T. Asano, W. J. Noble, Chem. Rev. 1978, 78, 407.
213. R. v. Eldik, T. Asano, W. J. L. Noble, Chem. Rev. 1989, 89, 549.
214. A. Drljaca, C. D. Hubbard, R. v. Eldik, T. Asano, M. V. Basilevsky, W. J. L. Noble, Chem. Rev. 1998, 98, 2167.
215. N. S. Isaacs, Liquid Phase High Pressure Chemistry, Wiley, New York, 1981.
216. A. E. Nicholson, G. W. Norrish, Discuss. Faraday Soc. 1956, 22, 104.
217. M. Yokawa, Y. Ogo, Makromol. Chem. 1976, 177, 429.
218. N. S. Isaacs, Liquid Phase High Pressure Chemistry, Wiley, New York, 1981, p. 106.
219. H. Keck, W. Schindler, F. Knoch, H. Kisch, Chem. Eur. J. 1997, 3, 1638.
220. S. J. Jin, S. Araki, Y. Butsugan, Bull. Chem. Soc. Jpn. 1993, 66, 1528.
221. B. Mauzé, L. Miginiac, Bull. Soc. Chim. Fr. 1973, 1832.
222. R. Arous-Chtara, J. L. Moreau, M. Gaudemar, J. Soc. Chim. Tunis. 1980, 3, 1.
223. W. Schindler, F. Knoch, H. Kisch, Chem. Ber. 1996, 129, 925.
224. K. Takaki, Y. Tsubaki, S. Tanaka, F. Beppu, Y. Fujiwara, Chem. Lett. 1990, 203.
225. H. Thies, H. Schöneberger, K. H. Bauer, Arch. Pharm. 1960, 293, 67.
226. H. Weiss, H. Kisch, unpublished work.
227. A. Mills, G. Williams, J. Chem. Soc., Faraday Trans. 1 1987, 83, 2647.
228. L. Feng, H. Wang, Z. Jin, Q. Li, U. Shi, J. Photochem. Photobiol. A: Chem. 1991, 56, 89.
229. R. L. Furey, R. O. Kan, Tetrahedron 1968, 24, 3085.