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Organic Sonoelectrochemistry

  • Chapter
Synthetic Organic Sonochemistry

Abstract

Electrosynthesis has a respected tradition in organic chemistry, and the Kolbe electrooxidation of aqueous acetate solutions is one of the oldest known organic reactions.1 Since then there have been reports at intervals until the development of high-dielectric organic solvents for routine use in the 1960s, which vastly increased the scope of systems that could be studied.2 Despite this, exploitation of organic electrosynthesis has lagged behind expectations,3 and it is an aim of workers in the field to redress this situation.

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References

  1. Kolbe, W. Ann.1849, 69, 257.

    Google Scholar 

  2. Organic Electrochemistry (Baizer, M. M.; Lund, H. Eds.), Marcel Dekker, New York, 3rd Ed., 1991.

    Google Scholar 

  3. See various industrial reports, for instance: (a) Atkinson, N. Process Engineering, Nov. 1988 p. 44; (b) Dotson, R.L. Interface 1994, 3, 95.

    Google Scholar 

  4. Moriguchi N. J. Chem. Soc. Jpn.1934, 55, 751–754.

    CAS  Google Scholar 

  5. Yeager, E.; Hovorka, F. J. Acoust. Soc. Am.1953, 25, 443–455.

    Google Scholar 

  6. Walker, R. in Advances in Sonochemistry (Mason, T.J. Ed.), JAI Press, London, 1993, Vol. 3, 125–144.

    Google Scholar 

  7. (a) Compton, R.G. Electrochimica Acta 1997, 42, 2919–2927; (b) Compton, R. G.; Marken, F.; Eklund, J. Electroanalysis 1997, 9, 509–522.

    Google Scholar 

  8. Walton, D.J.; Phull, S.S. in Advances in Sonochemistry (Mason, T.J. Ed.) JAI Press, London, 1996, Vol. 4, pp. 205–284.

    Google Scholar 

  9. 9 (a) Southampton Electrochemistry Group Instrumental Methods in Electrochemistry Ellis Horwood, 1985; (b) Laboratory Techniques in Electroanalytical Chemistry (Kissinger, P.T.; Heineman, W.R. Eds.), Marcel Dekker, New York, 1984; (c) Bockris, J.O.M.; Reddy, A.K.M. Modern Electrochemistry Plenum, Rosetta, 1970, Vols. 1 and 2.

    Google Scholar 

  10. (a) Christensen, P.A.; Hamnett, A. Techniques and Mechanisms in Electrochemistry Blackie Academic and Professional, London, 1994

    Google Scholar 

  11. Brett, C.M.A.; Oliviera Brett, A.M. Electrochemistry, Principles, Methods and Applications Oxford University Press, Oxford, 1993

    Google Scholar 

  12. Compton, R.G.; Sanders, G.H.W. Electrode Potentials Oxford Chemistry Primers, 1996

    Google Scholar 

  13. Fisher, A.C. Electrode Dynamics Oxford Chemistry Primers, 1996

    Google Scholar 

  14. Pletcher, D. A First Course in Electrode Processes The Electrochemical Consultancy, New York, 1991.

    Google Scholar 

  15. For example, Modern Aspects of Electrochemistry, N°27 (Bockris, J.O.M.; Conway, B.E.; White, R.E. Series Eds.), Plenum, New York, 1995.

    Google Scholar 

  16. Fry, A.J. Synthetic Organic Electrochemistry Harper and Row, New York, 1972.

    Google Scholar 

  17. (a) Kyriacou, D. Modern Electroorganic Chemistry Springer-Verlag, 1994

    Google Scholar 

  18. Shono, T. Electroorganic Synthesis in Best Synthetic Methods, Academic Press, 1991

    Google Scholar 

  19. Torii, S. Electroorganic Syntheses, Part I, Electrooxidations, 1995; Part 2, Electroreductions, 1996 VCH, Dearfield Beach, Florida, USA; (d) Techniques of Electroorganic Synthesis (Weinberg, N.L. Ed.), Part 3, Wiley, 1982.

    Google Scholar 

  20. Walsh, F. A First Course in Electrochemical Engineering Electrochemical Consultancy, Romsey, 1993.

    Google Scholar 

  21. Pletcher, D.; Walsh F. Industrial Electrochemistry Chapman and Hall, 2 Edn., 1990.

    Google Scholar 

  22. Albery, W. J. Electrode Kinetics Clarendon Press, 1975.

    Google Scholar 

  23. Physical Electrochemistry, Principles, Methods and Applications (Rubenstein, I. Ed.), Marcel Dekker, New York, 1995.

    Google Scholar 

  24. (a) Mason, T.J.; Lorimer, J.P. Sonochemistry Ellis Horwood, Chichester, 1988

    Google Scholar 

  25. Margulis, M.A.; Maltsev, A.N. Zh. Fiz. Khim.1969, 43, 1055–1059

    CAS  Google Scholar 

  26. Mason, T.J.; Lorimer, J.P.; Bates, D.M. Ultrasonics 1992, 30, 40–42.

    CAS  Google Scholar 

  27. Marken, F.; Compton, R.G. Ultrasonics Sonochemistry 1996, 3, S131–S134.

    Google Scholar 

  28. Compton, R.G.; Eklund, J.C.; Page, S.D.; Sanders, G. H.W.; Booth, J. J. Phys. Chem.1994, 98, 12410–12414.

    Google Scholar 

  29. Eklund, J.C.; Marken, F.; Waller, D.N.; Compton, R.G. Electrochemica Acta, 1996 42, 1541–1547.

    Google Scholar 

  30. Walton, D.J.; Phull, S.S.; Chyla, A.; Lorimer, J.P.; Mason, T.J.; Burke, L.D.; Murphy, M.; Compton, R.G.; Eklund, J.C.; Page, S.D. J. Appl. Electrochem.1995, 25, 1083–1090.

    CAS  Google Scholar 

  31. (a) Lorimer, J.P.; Pollet, B.; Phull, S.S.; Mason, T.J.; Walton, D.J.; Geissler, U. Electrochim Acta 1996, 41, 2737–2746

    Google Scholar 

  32. Klima, J.; Bernard, C.; Degrand, C. J. Electroanal. Chem.1994, 367, 297–300

    CAS  Google Scholar 

  33. Hagan, C.R.S.; Coury, L.A. Anal. Chem.1994, 66, 399–405

    CAS  Google Scholar 

  34. Jung, C.G.; Chapelle, F.; Fontana, A. ISE 47 th Meeting, Balatonfured, Hungary, 1996.

    Google Scholar 

  35. Compton, R.G.; Eklund, J.C.; Page, S. D.; Mason, T. J.; Walton, D.J. J. Appl. Electrochem.1996, 26, 775–784.

    CAS  Google Scholar 

  36. Compton, R.G.; Marken, F.; Rebbit T.O. J. Chem. Soc. Chem. Commun.1996, 1017–1018.

    Google Scholar 

  37. Compton, R. G.; Eklund, J.C.; Page, S.D.; Rebbit, T.O. J. Chem. Soc. Dalton Trans.1995, 389–393 1.

    Google Scholar 

  38. Compton, R. G.; Eklund, J. G; Page, S. D. J. Phys. Chem.1995, 99, 4211–4214.

    CAS  Google Scholar 

  39. Eklund, J. G; Waller, D. N.; Rebbit, T.O.; Marken, F.; Compton, R.G J. Chem. Soc. Perkin Trans. 2 1995, 1981–1984.

    Google Scholar 

  40. Lee, C.W.; Compton, R.G.; Eklund, J.G.; Waller, D.N. Ultrasonics Sonochemistry 1995, 2, S59–S62.

    Google Scholar 

  41. Marken, F.; Eklund, S.G.; Compton, R.G. J. Electroanal. Chem.1995, 395, 335–339.

    Google Scholar 

  42. Neppiras, A.E. Phys. Rep. Sect. Phys. Lett.1980, 61, 159–163.

    Google Scholar 

  43. Birkin, P. R.; Silva-Martinez, S. J. Chem. Soc. Chem. Commun.1995, 1807–1808.

    Google Scholar 

  44. Leighton, T.G. The Acoustic Bubble Academic Press, 1994.

    Google Scholar 

  45. Benahcene, A.; Labbe, P.; Pétrier, C.; Reverdy, G. New J. Chem.1995, 19, 989–995.

    Google Scholar 

  46. Walton, D.J.; Murphy, M.; Burke, L.D. Electrochimica Acta 1996, 41, 2747–2751.

    Google Scholar 

  47. Wilis, B.A. Mineral Processing Technology, 5th Ed., Pergamon, New York, 1992.

    Google Scholar 

  48. Zholshibekova, M.R.; Ischenko, V.V.; Baishulakov, A.A.; Malakhov, Y.A. Komplenskn Ispol’z Miner. Syr’ya 1983, 2, 7–9; Chem. Abstr. 1983, 99, 74461.

    Google Scholar 

  49. Chanturiya, V.A.; Zholshibekova, M.R.; Malakhov, Y.V. Elektron. Obrab. Mater.1983, 2, 76–77.

    Google Scholar 

  50. Chanturiya, V.A.; Dimitrieva, L.L.; Zholshibekova, M.R.; Malakhov, Y.V. Vestn. Akad. Nauk Kaz. SSR 1984, 9, 47–52; Chem. Abstr.1985, 102, 49131g.

    Google Scholar 

  51. Shautenov, M.R., Malakhov, Y.V. Kompleksn. Ispol’z Miner. Syr’ya.1988, 3, 24–26; Chem. Abstr.1988, 109, 25658c.

    Google Scholar 

  52. Chanturiya, V.A.; Dimitrieva, L.L. in Flotatsionnye Reagenty (Gol’man, A.M.; Dimitrieva, L.L. Eds.) Nauka, Moscow, 1986.

    Google Scholar 

  53. Tsonkov, T.; Paulapanski, M.; Djendova, S. Oxid. Commun.1994, 17, 321–325.

    CAS  Google Scholar 

  54. Connors, T.F.; Rusling, J.F. Chemosphere 1984, 13, 415–420.

    CAS  Google Scholar 

  55. Schweizer, S.; Rusling, J.F.; Huang, G. Chemosphere 1994, 28, 961–970.

    CAS  Google Scholar 

  56. Zhang, S.; Rusling, J.F. Environ. Sci. Technol.1993, 27, 1375–1380.

    CAS  Google Scholar 

  57. Rusling, J.F. Acc. Chem. Res.1991, 24, 75–81

    CAS  Google Scholar 

  58. id. in Electroanalytical Chemistry (Bard, A.J. Ed.), Marcel Dekker, New York, 1994, Vol. 19, pp. 1–88; (c) id. in Modern Aspects of Electrochemistry (Conway, B.E.; Bockris, J.O.M. Eds.), Plenum Press, New York 1994, 26, pp. 49–104.

    Google Scholar 

  59. Franklin, T.C.; Darlington, J.; Solouki, T. J. Electrochem. Soc. 1991, 138, 747–750.

    Google Scholar 

  60. Franklin, C.; Darlington, J.; Adeniyl, W.K. J. Electrochem. Soc.1990, 137, 2124–2126.

    CAS  Google Scholar 

  61. Mizera, J. Waste Treatment and Disposal 1982, Pol 2.

    Google Scholar 

  62. Matschiner, H.; Wildner, K.; Thiele, W. German Patent DE 4430391 1994; Chem. Abstr.1996, 124, 21091z.

    Google Scholar 

  63. Gindre, M.; Josiane, E. French Patent 2724163 1994; Chem. Abstr.1996, 124, 32489j.

    Google Scholar 

  64. Eberson, L.; Utley, J.H.P. in Organic Electrochemistry (Baizer, M.M.; Lund, H. Eds.), Marcel Dekker, New York, 2 Ed., 1982.

    Google Scholar 

  65. Vassiliev, Y.B.; Grinberg, V.A. J. Electroanal. Chem. 1991, 308, 1–16, and papers cited.

    CAS  Google Scholar 

  66. Hawkes, G.E.; Utley, J.H.P.; Yates, G.B. J. Chem. Soc. Perkin Trans. 21976, 1709–1716.

    Google Scholar 

  67. Walton, D.J.; Chyla, A.; Lorimer, J.P.; Mason, T.J.; Smith, G. J. Chem. Soc. Chem. Commun.1989, 603–604 1.

    Google Scholar 

  68. Luche, J.L.; Cintas, P. in Active Metals: Preparation, Characterisation, Applications (Fürstner, A. Ed.), VCH, Weinheim, 1996, pp. 133–190.

    Google Scholar 

  69. Walton, D.J.; Chyla, A.; Lorimer, J.P.; Mason, T.J. Ultrasonics Conference 1989, 1241.

    Google Scholar 

  70. Walton, D.J.; Chyla, A.; Lorimer, J.P.; Mason, T.J. Synth. Commun.1990, 20, 1843–1852.

    CAS  Google Scholar 

  71. Coleman, J.P.; Lines, R.; Utley, J.H.P.; Weedon, B.C.L. J. Chem. Soc. Perkin Trans. 21974, 1064–1069.

    Google Scholar 

  72. Koehl, W.J. J. Org. Chem.1967, 32, 614–618.

    CAS  Google Scholar 

  73. Bonner, W.A.; Mango, F.D. J. Org. Chem.1964, 29, 430–435.

    CAS  Google Scholar 

  74. Tashino, M.; Tsuzuki, W.; Goto, H.; Ogashasa, S.; Mataka, S. J. Labelled Comp.; Radiopharmaceuticals 1991, 29, 475–484.

    Google Scholar 

  75. Tashiro, M.; Tsuzuki, H.; Goto, H.; Makata, S. Chemistry Express 1991, 6, 403–406.

    CAS  Google Scholar 

  76. Walton, D.J.; Phull, S.S.; Mason, T.J.; Lorimer, J.P.; Geissler, D. J. to be published.

    Google Scholar 

  77. Walton, D. J.; Geissler, U.; Durham, A. Proc. World Congress on Ultrasonics, Berlin, 1995 p 659.

    Google Scholar 

  78. Gigi, S.; Paucescu, V.; Jurth, S. Romanian Patent 1980 RO 72382; Chem. Abstr.1982, 96, 151408x.

    Google Scholar 

  79. Ono, Y.; Mishiki, Y.; Nonaka, T. Chem. Lett.1994, 1623–1626 1.

    Google Scholar 

  80. Cheng, P.C.; Nonaka, T.; Chou, T.C. Bull Chem. Soc. Jpn.1991, 64, 1911–1915.

    CAS  Google Scholar 

  81. Atobe, M.; Matsuda, K.; Nonaka, T. Electroanalysis 1996, 8, 784–788.

    CAS  Google Scholar 

  82. Sunashima, K. T.; Nonaka, T. Chem. Lett.1995, 862 1.

    Google Scholar 

  83. Durrant, A.; François, W.; Reisse, J.; Kirsch-De Mesmaeker, A. Electrochimica Acta 1996, 41, 277–284.

    Google Scholar 

  84. Atobe, M.; Nonaka, T. Chem. Lett.1995, 669–670 4.

    Google Scholar 

  85. Atobe, M.; Matsuda, K.; Nonaka, T. Denki Kagaku Oyobi Kogyo Butsuri Kagaku 1994, 62, 1298–1299; Chem. Abstr. 1995, 122, 117297f.

    Google Scholar 

  86. Fry, A.J.; Touster, J.; Sirisoma, N.U.; Raimundo, B. Electroorganic Synthesis M.M. Baizer Memorial Symposium (Little, D.R.; Weinberg, N.L. Eds.), Marcel Dekker, New York, 1991 pp. 99–104.

    Google Scholar 

  87. Touster, J. PhD Thesis, Wesleyan University, 1991.

    Google Scholar 

  88. Fry, A.J.; Bujanauskas, P. J. Org. Chem.1978, 43, 3157–3163.

    CAS  Google Scholar 

  89. Fry, A.J.; O’Dea, J. J. Org. Chem.1975, 40, 3625–3631.

    CAS  Google Scholar 

  90. Fry, A.J.; Herr, D. Tetrahedron Lett 1978, 20, 1721–1724.

    Google Scholar 

  91. Fry, A.J.; Lefor, A.T. J. Org. Chem.1979, 44, 1270–1273.

    CAS  Google Scholar 

  92. Gautheron, B.; Tainturier, G.; Degrand, C. J. Am. Chem. Soc.1985, 107, 5579–5581.

    CAS  Google Scholar 

  93. Gautheron, B.; Tainturier, G.; Degrand, C. Organometallics 1986, 5, 942–944.

    Google Scholar 

  94. Degrand, C. J. Chem. Soc. Chem. Commun.1986, 1113–1115 1.

    Google Scholar 

  95. Degrand, C.; Prest, R.; Compagnon, P.L. J. Org. Chem.1987, 52, 5229–5233.

    CAS  Google Scholar 

  96. Degrand, C.; Prest, R.; Nour, M. Phosphorus Sulfur 1987, 38, 201–209.

    CAS  Google Scholar 

  97. Shono, T.; Kashimura, S.; Ishifune, M.; Nishida, R. J. Chem. Soc. Chem. Commun.1990, 1160–1161.

    Google Scholar 

  98. Hengge, E.; Firgo, H. J. Organomet. Chem.1981, 212, 155–161.

    CAS  Google Scholar 

  99. Hengge, E.; Latscher, G. Monatsh. Chem.1978, 109, 1217–1225.

    CAS  Google Scholar 

  100. Shono, T.; Kashiwamura, S.; Nishida, P. Jpn. Kokai Tokkyo Koho JP326 4683 1991; Chem. Abstr. 1992, 116, 161234h.

    Google Scholar 

  101. Shono, T.; Kashiwamura, S.; Nishida, P.; Murase, H. Jpn. Kokai Tokkyo Koho JP 05306483 1993; Chem. Abstr. 1994, 120, 17 6388t.

    Google Scholar 

  102. Shono, T.; Kashiwamura, S.; Nishida, P.; Kawasaki, S. Eur. Pat. App. EP446578 1991; Chem. Abstr.1992, 116, 21 727w.

    Google Scholar 

  103. Shono, T.; Kashiwamura, S.; Nishida, P.; Murase, H. Jpn. Kokai Tokkyo Koho JP 05306340 1993; Chem. Abstr. 1994, 120, 299615x.

    Google Scholar 

  104. Shono, T.; Kashiwamura, S.; Nishida, P.; Murase, H. Jpn. Kokai Tokkyo Koho JP 05306342 1993; Chem. Abstr. 1994, 120, 194194f.

    Google Scholar 

  105. Shono, T.; Kashiwamura, S.; Nishida, P.; Kawasaki, S. Jpn. Kokai Tokkyo Koho JP 05230317/8 1993; PCT Int. Appl. W09306152 1993; Chem. Abstr.1994, 120, 56009y.

    Google Scholar 

  106. Akbulut, U.; Toppare, L.; Yurttas, B. Polymer 1986, 27, 803–806.

    Google Scholar 

  107. Akbulut, U.; Fernandez, J.E.; Birke, R.L. J. Polym. Sci. Chem.1975, 13, 133–149.

    CAS  Google Scholar 

  108. Akbulut, U.; Toppare, L.; Yurttas, B. Brit. Polym. J.1986, 18, 273–276.

    CAS  Google Scholar 

  109. Eren, S.; Toppare, L.; Akbulut, U. Polymer Commun.1987, 28, 36–38.

    Google Scholar 

  110. Akbulut, U.; Eren, S.; Toppare, L.K. J. Macromol. Sci. Chem.1984, A21, 335–342.

    Google Scholar 

  111. Aybar, S.P.; Hacioglu, B.; Akbulut, U. J. Poly. Sci. Part A, Polym. Chem.1991, 29, 1971–1976.

    CAS  Google Scholar 

  112. The Handbook of Conducting Polymers (Skotheim, T.A. Ed.), Marcel Dekker, New York 1986, Vols. 1 and 2.

    Google Scholar 

  113. Walton, D.J. in Electronic Materials, from Silicon to Organics (Miller, L. S.; Mullin, J. B. Eds.), Plenum Press, 1991.

    Google Scholar 

  114. Walton, D.J.; Hall, C.E.; Chyla, A. The Analyst 1992, 117, 1305–1311.

    Google Scholar 

  115. Osawa, S.; Ito, M.; Tanaka, K.; Kuwano, J. Synthetic Metals 1987, 18, 145–150.

    Google Scholar 

  116. Osawa, S.; Ito, M; Tanaka, K.; Kuwano, J. J. Polym. Sci. Part B, Polym. Physics 1992, 30, 19–24.

    CAS  Google Scholar 

  117. Walton, D. J.; Geissler, U.; Ryley, S.; Campbell, C.; Evans, J. ISE 47 th Meeting, Balatonfured, Hungary, 1996.

    Google Scholar 

  118. Faulkner, L.R.; Bard, A.J. in Creation and Detection of the Excited State (Ware, W.R. Ed.) Marcel Dekker, New York, 1976.

    Google Scholar 

  119. Phull, S.S. Ph.D Thesis University of Warwick, UK, 1990 and references therein.

    Google Scholar 

  120. Walton, D.J.; Phull, S.S.; Lorimer, J.P.; Mason, T.J. Ultrasonics 1992, 30, 186–191.

    Google Scholar 

  121. Walton, D.J.; Phull, S.S.; Bates, D.M.; Lorimer, J.P.; Mason, T.J. Electrochimica Acta 1993, 38, 307–310.

    Google Scholar 

  122. Burgess, A.E.; Feigneux, M.; Hapher, M.J. 4 th Meeting, European Society of Sonochemistry Blankenberge, Belgium 1994.

    Google Scholar 

  123. Zhivnov, V.A.; Rumyantsev, I.Y.; Tomin, V.I.; Dezhkunov, N.V.; Prokhorenko, P.P. Vesti Akad. Navuk SSR Ser. Fiz.-Tekh. Navuk 1976, 3, 86–88; Chem. Abstr.1977, 86, 10234u.

    Google Scholar 

  124. Zhivnov, V.A.; Rumyantsev, I.Y.; Tomin, V.I. Spectrosc. Lett.1977, 10, 763–770; Chem. Abstr.1978, 88, 43149q.

    CAS  Google Scholar 

  125. Walton, D.J.; Phull, S.S.; Colton, C.; Richards, P.; Chyla, A.; Javed, T.; Clarke, L.; Lorimer, J.P.; Mason, T.J. Ultrasonics Sonochemistry 1994, 1, S23-S26.

    Google Scholar 

  126. Dincturk, S.; Jackson, R. J. Chem. Soc. Perkin Trans. 2 1981, 1127–1131.

    Google Scholar 

  127. Fisher, T.H.; Dersheim, S.M.; Crewitt, M.I. J. Org. Chem. 1990, 55, 1040 4043.

    CAS  Google Scholar 

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Walton, D.J., Mason, T.J. (1998). Organic Sonoelectrochemistry. In: Synthetic Organic Sonochemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1910-6_7

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