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Electrofluorination of Organic Compounds

  • Fred G. Drakesmith
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 193)

Abstract

The three principal electrochemical methods are described by which fluorine can be directly introduced into organic compounds, namely electrolysis in molten salts or fluoride ion solutions, electrolysis in molten potassium fluoride/hydrogen fluoride melts at porous anodes, and electrolysis in anhydrous hydrogen fluoride at nickel anodes. Using examples from the past decade, it is aimed to demonstrate that electrofluorination in its various forms has proved to be an increasingly versatile tool in the repertoire of the synthetic chemist. Each method is described in terms of its essential characteristics, reaction parameters, synthetic utility, advantages and disadvantages, patent protection, and potential for commercial exploitation. The different mechanisms proposed to explain each process are critically reviewed.

Keywords

Electro- Simons Anodic Fluroination Electron-transfer 

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5 References

  1. 1.
    Uneyama K (1991) Journal of Synthetic Organic Chemistry Japan 49:61Google Scholar
  2. 2.
    Zappi GD (1996) Watts New Electrosynthesis Co. Inc. 2:2Google Scholar
  3. 3.
    Hollitzer E, Sartori P (1988) International Chemical Engineering 28:221Google Scholar
  4. 4.
    Haufe G (1996) Journal für Prackische Chemie Chemiker-Zietung 338:99CrossRefGoogle Scholar
  5. 5.
    Meurs JHH, Eilenberg W (1991) Tetrahedron 47:705CrossRefGoogle Scholar
  6. 6.
    Laurent E, Lefranc H, Tardivel R (1984) Nouv J Chim 8:345Google Scholar
  7. 7.
    Laurent E, Marquet B, Tardivel R, Thiebault H (1986) Bull Soc Chim Fr 955Google Scholar
  8. 8.
    Andres DF, Laurent EG, Marquet BS, Benotmane H, Bensadat A (1995) Tetrahedron 51: 2605CrossRefGoogle Scholar
  9. 9.
    Rozhkov IN (1976) Russ Chem Rev 45:615CrossRefGoogle Scholar
  10. 10.
    Ludman CL, McCarron EM, O’Malley RF (1972) J Electrochem Soc 119:874CrossRefGoogle Scholar
  11. 11.
    Makino K, Yoshioka H (1988) J Fluorine Chem 39:435CrossRefGoogle Scholar
  12. 12.
    Carpenter JF, Ekes LH, King PF, Mariani HA, Mirza Zadeh M, O’Malley RF, Roman VJ (1983) J Electrochem Soc 130:2170CrossRefGoogle Scholar
  13. 13.
    Meurs JHH, Sopher DW, Eilenberg W (1989) Angew Chem 101; 955; (1989) Angew Chem Int Ed Engl 28:927CrossRefGoogle Scholar
  14. 14.
    Momota K, Morita M, Matsuda Y (1993) Electrochim Acta 38:619CrossRefGoogle Scholar
  15. 15.
    Patent No. J63038591Google Scholar
  16. 16.
    Momota K, Morita M, Matsuda Y (1993) Electrochimica Acta 38:1123CrossRefGoogle Scholar
  17. 17.
    Momota K, Kato K, Morita M, Matsuda Y (1994) Electrochimica Acta 39:41CrossRefGoogle Scholar
  18. 18.
    Momota K, Kato K, Morita M, Matsuda Y (1994) Electrochimica Acta 39:681CrossRefGoogle Scholar
  19. 19.
    Momota K, Horio H, Kato K, Morita M, Matsuda Y (1995) Electrochimica Acta 40:233CrossRefGoogle Scholar
  20. 20.
    Horio H, Momota K, Kato K, Morita M, Matsuda Y (1996) Electrochimica Acta 41:1611CrossRefGoogle Scholar
  21. 21.
    Morita M, Momota K, Horio H, Kato K, Matsuda Y (1994) Denki Kagaku 62:1196Google Scholar
  22. 22.
    Morita M, Momota K, Horio H, Kato K, Matsuda Y (1994) Denki Kagaku 62:33Google Scholar
  23. 23.
    Morita M, Hayakawa Y, Momota K, Yonezawa T, Kato K, Matsuda Y (1995) J Appl Electrochemistry 25:651Google Scholar
  24. 24.
    Patent No. JP05320967-AGoogle Scholar
  25. 25.
    Patent No. J63111192Google Scholar
  26. 26.
    Patent No. GB2191480Google Scholar
  27. 27.
    Laurent E, Marquet B, Tardivel R (1989) Tetrahedron 45:4431CrossRefGoogle Scholar
  28. 28.
    Laurent E, Marquet B, Tardivel R (1991) Tetrahedron 47:3969CrossRefGoogle Scholar
  29. 29.
    Laurent E, Marquet B, Tardivel R (1990) Tetrahedron 49:115Google Scholar
  30. 30.
    Kabore L, Chebli S, Faure R, Laurent E, Marquet B (1990) Tetrahedron Lett 31:3137CrossRefGoogle Scholar
  31. 31.
    Patent No. FR2641002Google Scholar
  32. 32.
    Yoneda N, Chen S-Q, Hatakeyama T, Hara S, Fukuhara T (1994) Chem Soc Japan, Chemistry Letters 849Google Scholar
  33. 33.
    Patent No. JP07292490-AGoogle Scholar
  34. 34.
    Fuchigami T, (1994) Rev Heteroatom Chem 10:155Google Scholar
  35. 35.
    Fuchigami T, Shimojo M, Konno A (1995) J Org Chem 60:3459CrossRefGoogle Scholar
  36. 36.
    Konno A, Naito W, Fuchigami T (1992) Tetrahedron Lett 33:7017CrossRefGoogle Scholar
  37. 37.
    Fuchigami T, Hayashi T, Konno A (1992) Tetrahedron Lett 33:316CrossRefGoogle Scholar
  38. 38.
    Erian AW, Konno A, Fuchigami T (1994) Tetrahedron Lett 35:7245CrossRefGoogle Scholar
  39. 39.
    Brigaud T, Laurent E (1990) Tetrahedron Lett 31:2287CrossRefGoogle Scholar
  40. 40.
    Narizuka S, Konno A, Matsuyama H, Fuchigami T (1993) J Electrochem Soc Jpn 61:868Google Scholar
  41. 41.
    Narizuka S, Fuchigami T (1995) Bioorg Med Chem Lett 5:1293CrossRefGoogle Scholar
  42. 42.
    Narizuka S, Fuchigami T, Konno A (1992) J Org Chem 57:3755CrossRefGoogle Scholar
  43. 43.
    Sono M, Toyoda N, Shimizu K, Noda E, Shizuri Y, Tori M (1996) Chem Pharm Bull 44:1141Google Scholar
  44. 44.
    Sono M, Toyoda N, Shimizu K, Noda E, Shizuri Y, Tori M (1994) Tetradron Lett 35:9237CrossRefGoogle Scholar
  45. 45.
    Suda K, Hotoda K, Aoyagi M, Takanami T (1995) J Chem Soc Perkin Trans 1 1327CrossRefGoogle Scholar
  46. 46.
    Patent No. J01029366Google Scholar
  47. 47.
    Brigaud T, Laurent A, Laurent E (1991) Phosphorus, Sulfur, and Silicon 59:153CrossRefGoogle Scholar
  48. 48.
    Yoshiyama T, Fuchigami T (1992) Chem Lett 1995Google Scholar
  49. 49.
    Fuchigami T, Fujita T, Konno A (1994) Tetrahedron Lett 35:4153CrossRefGoogle Scholar
  50. 50.
    Popova OV, Kovalenko EI, Sherstyukova ND (1995) Russian Journal of Applied Chemistry 68:995Google Scholar
  51. 51.
    Patent No. RU2048471-CGoogle Scholar
  52. 52.
    Yoneda N, Chen S-Q, Hatakeyama T, Hara S, Fukuhara T, Sekiguchi M (1995) Tetrahedron Lett 36:6511CrossRefGoogle Scholar
  53. 53.
    Childs WV (1982) in Weinberg NL (ed) Technique of Electroorganic Synthesis Vol V Part III. John Wiley & Sons, New York p 341Google Scholar
  54. 54.
    Alsmeyer YW, Childs WV, Flynn RM, Moore GGI, Smeltzer JC (1994) in Electrochemical Fluorination and Its Applications in Banks RE et al. (eds) Organofluorine Chemistry: Principles and commercial Applications. Plenum Press, New York p 121Google Scholar
  55. 55.
    Childs WV, Christensen L, Klink FW, Koplin CF (1991) in Lund H, Baizer MM (eds) Organic Electrochemistry 3rd Edn Chapter 6. Marcel Dekker, New York, p 1113Google Scholar
  56. 56.
    Childs WV, Fall DJ (1987) 172nd Meeting of the Electrochem Soc paper no. 1345Google Scholar
  57. 57.
    Tasaka A, Sakaguchi H, Aki R, Ihara H, Saka K, Yamamoto T (1985) J Fluorine Chem 27:23CrossRefGoogle Scholar
  58. 58.
    Pearlson WH (1989) J Fluorine Chem 32:29CrossRefGoogle Scholar
  59. 59.
    Childs WV, Christensen L, Klink FW, Koplin CF (1991) in Lund H, Baizer MM (eds) Organic Electrochemistry 3rd Edn Chapter 6. Marcel Dekker, New York, p 1103Google Scholar
  60. 60.
    Sartori P (1990) Bull Electrochem 6:471Google Scholar
  61. 61.
    Hollitzer E, Sartori P (1986) Chem Ing Tech 58:31CrossRefGoogle Scholar
  62. 62.
    Rozhkov IN (1983) in Baizer MM, Lund H (eds) Organic Electrochemistry 2nd Edn Chapter 24. Marcel Dekker, New York, p 805Google Scholar
  63. 63.
    Abe T, Nagase S (1982) in Banks RE (ed) Preparation, Properties and Industrial Application of Organofluorine Compounds. Ellis Horwood, Chichester p 19Google Scholar
  64. 64.
    Nagase S (1967) in Tarrant P (ed) Fluorine Chemistry Reviews Vol 1. Marcel Dekker, New York p 77Google Scholar
  65. 65.
    Weinberg NL (1975) in Weinberg NL (ed) Technique of Electrochemical Synthesis Part II. Wiley, New York p 1Google Scholar
  66. 66.
    Burdon J, Tatlow JC (1960) in Stacey M, Tatlow JC, Sharpe AG (eds) Advances in Fluorine Chemistry Vol1. Butterworths, London p 129Google Scholar
  67. 67.
    Rudge AJ (1967) in Kuhn AT (ed) Industrial Electrochemical Processes. Marcel Dekker, New York p 71Google Scholar
  68. 68.
    Hollitzer E, Sartori P (1988) International Chemical engineering 28:221Google Scholar
  69. 69.
    Furin GG, Gambaretto GP (1996) Direct Fluorination of Organic Compounds Chapter 4. Cooperativa Libraria Editrice Universita di PadovaGoogle Scholar
  70. 70.
    Ròdiger S, Dimitrov A, Hottman K (1996) J Fluorine Chem 76:155CrossRefGoogle Scholar
  71. 71.
    Drakesmith FG, Hughes DA (1979) J Appl Electrochem 9:685CrossRefGoogle Scholar
  72. 72.
    Sartori P (1963) Angew Chem 75:417CrossRefGoogle Scholar
  73. 73.
    Nagase S, Tanaka K, Baba H (1965) Bull Chem Soc Jpn 38:835CrossRefGoogle Scholar
  74. 74.
    Nagase S, Tanaka K, Baba H (1966) Bull Chem Soc Jpn 39:219CrossRefGoogle Scholar
  75. 75.
    Zuliani G, Pizzolotto G (1972) Nuova Chim 48:47Google Scholar
  76. 76.
    Drakesmith FG, Hughes DA (1976) J Appl Electrochem 6:23CrossRefGoogle Scholar
  77. 77.
    Jpn Kokai Tokkyo Koko 80–90 508 (to Tokushima Soda) (1980) Chem Abs 93:205 373Google Scholar
  78. 78.
    Abe T, Nagase S (1982) in Banks RE (ed) Preparation, Properties and Industrial Application of Organofluorine Compounds. Ellis Horwood, Chichester p 20Google Scholar
  79. 79.
    Patent No. WO9413857-AGoogle Scholar
  80. 80.
    Conte L, Fraccaro C, Napoli M (1986) J Fluorine Chem 34:183CrossRefGoogle Scholar
  81. 81.
    Naito Y, Inoue Y, Ono T, Arakawa Y, Fukaya C, Yokoyama K, Kobayashi Y, Yamanouchi K (1984) J Fluorine Chem 26:485CrossRefGoogle Scholar
  82. 82.
    Naito Y, Inoue Y, Ono T, Arakawa Y, Fukaya C, Yokoyama K, Kobayashi Y, Yamanouchi K (1985) J Fluorine Chem 27:333CrossRefGoogle Scholar
  83. 83.
    Naito Y, Inoue Y, Ono T, Arakawa Y, Fukaya C, Yokoyama K, Yamanouchi K (1988) J Fluorine Chem 38:303CrossRefGoogle Scholar
  84. 84.
    Naito Y, Inoue Y, Ono T, Arakawa Y, Fukaya C, Yokoyama K, Yamanouchi K (1989) J Fluorine Chem 43:67CrossRefGoogle Scholar
  85. 85.
    Meinert H, Fackler R, Mader J, Reuter P, Rohlke W (1991) J Fluorine Chem 51:53CrossRefGoogle Scholar
  86. 86.
    Meinert H, Fackler R, Mader J, Reuter P, Rohlke W (1992) J Fluorine Chem 59:351CrossRefGoogle Scholar
  87. 87.
    Patent No. EP-415264-AGoogle Scholar
  88. 88.
    Patent No. SU1427780Google Scholar
  89. 89.
    Patent No. J63089690Google Scholar
  90. 90.
    Moldavsky DD, Kaurova GI, Bispen TA, Furin GG (1993) J Fluorine Chem 63:193CrossRefGoogle Scholar
  91. 91.
    Patent No. DD-275079Google Scholar
  92. 92.
    Patent No. DD-275078Google Scholar
  93. 93.
    Patent No. DD-275077Google Scholar
  94. 94.
    Patent No. DD-273290Google Scholar
  95. 95.
    Patent No. DD-280130Google Scholar
  96. 96.
    Patent No. WO9205142-AGoogle Scholar
  97. 97.
    Patent No. J62127488Google Scholar
  98. 98.
    Moore GGI, Hansen JC, Bartett TM, Waddell JE, Jewell KM, Kestner TA, Payfer RM (1986) J Fluorine Chem 32:41CrossRefGoogle Scholar
  99. 99.
    Patent No. EP-492823-AGoogle Scholar
  100. 100.
    Patent No. US4788339Google Scholar
  101. 101.
    Patent No. EP-214852Google Scholar
  102. 102.
    Dimitrov A, Radeck W, Rüdiger S (1991) J Fluorine Chem 52:317CrossRefGoogle Scholar
  103. 103.
    Dimitrov A, Rüdiger S, Pauli J (1994) J Fluorine Chem 66:223CrossRefGoogle Scholar
  104. 104.
    Patent No. DD-294514Google Scholar
  105. 105.
    Abe T, Hayashi E, Baba H, Fukaya H (1990) J Fluorine Chem 48:257CrossRefGoogle Scholar
  106. 106.
    Hayashi E, Fukaya H, Abe T, Omori K (1991) J Fluorine Chem 52:133CrossRefGoogle Scholar
  107. 107.
    Hayashi E, Fukaya H, Abe T, Hayakawa Y, Omori K (1991) J Fluorine Chem 53:199CrossRefGoogle Scholar
  108. 108.
    Hayashi E, Fukaya H, Abe T, Hayakawa Y, Baba H, Ishikawa S, Asahino K (1992) J Fluorine Chem 57:101CrossRefGoogle Scholar
  109. 109.
    Hayashi E, Fukaya H, Abe T, Hayakawa Y, Baba H, Nishida M (1994) J Fluorine Chem 66: 193CrossRefGoogle Scholar
  110. 110.
    O’Sullivan EJM, Klink FW, Liu CC, Yeager EB (1985) J Electrochem Soc 132:2424CrossRefGoogle Scholar
  111. 111.
    Sartori P, Jüschke R (1994) J Fluorine Chem 69:157CrossRefGoogle Scholar
  112. 112.
    Gard GL, Hamel NN, Mohtasham J, Waterfeld A, Mews R (1991) J Fluorine Chem 55:313CrossRefGoogle Scholar
  113. 113.
    Ignat’ev NV, Datsnko SD, Yagopolskii LM, Dimitrov A, Radeck W, Ròdiger S (1995) J Fluorine Chem 74:181CrossRefGoogle Scholar
  114. 114.
    Patent No.US5486271-AGoogle Scholar
  115. 115.
    Patent No. US5318674-AGoogle Scholar
  116. 116.
    Patent No. EP-444822Google Scholar
  117. 117.
    Geisler K, Koemm U, Metzinger H-G (1984) J Fluorine Chem 24:17CrossRefGoogle Scholar
  118. 118.
    Patent No. DE4218562-AGoogle Scholar
  119. 119.
    Patent No. WO9521949-AGoogle Scholar
  120. 120.
    Patent No. EP-455399Google Scholar
  121. 121.
    Dresdner RD, Young JA (1959) J Amer Chem Soc 81:574CrossRefGoogle Scholar
  122. 122.
    Kazakov VY, Savelev LA, Dzerzhinskaya RA, Shuskkin EA, Gudimov IL (1968) Zhur Prikladnoi Khimi 41:2212Google Scholar
  123. 123.
    Conte L, Napoli M, Gambaretto GP (1985) J Fluorine Chem 30:89CrossRefGoogle Scholar
  124. 124.
    Drakesmith FG, Hughes DA (1986) J Fluorine Chem 32:103CrossRefGoogle Scholar
  125. 125.
    Patent No. J62060885Google Scholar
  126. 126.
    Klink FW, Kucera F, Wasser DJ, Liu CC (1986) J Fluorine Chem 32:77CrossRefGoogle Scholar
  127. 127.
    Klink FW, Wasser DJ, Liu CC (1986) J Fluorine Chem 32:89CrossRefGoogle Scholar
  128. 128.
    Comninellis C, Jaret p, Plattner E (1974) J Appl Electrochem 4:289CrossRefGoogle Scholar
  129. 129.
    Prokop HW, Zhou H-J, Xu S-Q, Wu C-H, Chuey SR, Liu CC (1989) J Fluorine Chem 43:257CrossRefGoogle Scholar
  130. 130.
    Patent No. J62224690Google Scholar
  131. 131.
    Patent No. J62133094Google Scholar
  132. 132.
    Patent No. J61163288Google Scholar
  133. 133.
    Patent No. DE4208364-AGoogle Scholar
  134. 134.
    Chambers RD, Grievson B, Drakesmith FG, Powell RL (1985) J Fluorine Chem 29:323CrossRefGoogle Scholar
  135. 135.
    Chambers RD, Fuss RW, Jones M, Sartori P, Swales AP, Herkelmann R (1990) J Fluorine Chem 49:409CrossRefGoogle Scholar
  136. 136.
    Napoli M, Scipioni A, Gambaretto GP, Carlini FM, Bertola M (1994) J Fluorine Chem 67: 261CrossRefGoogle Scholar
  137. 137.
    Napoli M, Conte L, Gambaretto GP, Carlini FM (1989) J Fluorine Chem 45:213CrossRefGoogle Scholar
  138. 138.
    Patent No. EP-582192-AGoogle Scholar
  139. 139.
    Patent No. RU2026889-CGoogle Scholar
  140. 140.
    Patent No. SU1666581-AGoogle Scholar
  141. 141.
    Patent No. US5387323-AGoogle Scholar
  142. 142.
    Patent No. JP06212468-AGoogle Scholar
  143. 143.
    Patent No. JP06146048-AGoogle Scholar
  144. 144.
    Patent No. JP06146043-AGoogle Scholar
  145. 145.
    Patent No. JP05025671-AGoogle Scholar
  146. 146.
    Patent No. JP04232289-AGoogle Scholar
  147. 147.
    Patent No. J02030785Google Scholar
  148. 148.
    Patent No. JP05059579-AGoogle Scholar
  149. 149.
    Patent No. JP06057475-AGoogle Scholar
  150. 150.
    Patent No. JP04143288-AGoogle Scholar
  151. 151.
    Patent No. EP-690147-AGoogle Scholar
  152. 152.
    Patent No. DE4226758-AGoogle Scholar
  153. 153.
    Patent No. DE4010961Google Scholar
  154. 154.
    Patent No. JP05320968-AGoogle Scholar
  155. 155.
    Patent No. J01312095Google Scholar
  156. 156.
    Patent No. J01275789Google Scholar
  157. 157.
    Weinberg NL (1975) in Weinberg NL (ed) Technique of Electrochemical Synthesis Part II. Wiley, New York p 15Google Scholar
  158. 158.
    Voitivich YN, Kazakov VY (1971) Zhur Priklad Khim 44:2452Google Scholar
  159. 159.
    Burdon J, Parsons IW, Tatlow JC (1972) Tetrahedron 28:43CrossRefGoogle Scholar
  160. 160.
    Clarke JS, Kuhn AT (1977) J Electroanal Chem 85:299CrossRefGoogle Scholar
  161. 161.
    Watanabe N, Haruta M (1979) Abstracts of the First Regular Meeting of Soviet-Japanese Fluorine Chemists, Tokyo, p 39Google Scholar
  162. 162.
    Lines D, Sutcliffe H (1981) J Fluorine Chem 17:423CrossRefGoogle Scholar
  163. 163.
    Ròdiger S, Dimitrov A, Hottman K (1996) J Fluorine Chem 76:155CrossRefGoogle Scholar
  164. 164.
    Hackerman N, Snavely ES, Fiel LD (1967) Corrosion Science 7:39CrossRefGoogle Scholar
  165. 165.
    Rudge AJ (1967) in Kuhn AT (ed) Industrial Electrochemical Processes. Marcel Dekker, New YorkGoogle Scholar
  166. 166.
    Simons JH (1950) in Fluorine Chemistry Vol 1, Academic Press, New YorkGoogle Scholar
  167. 167.
    Childs WV, Christensen L, Klink FW, Koplin CF (1991) in Lund H, Baizer MM (eds) Organic Electrochemistry 3rd Edn Chapter 6. Marcel Dekker, New York, p. 1109Google Scholar
  168. 168.
    Chang B, Yanase H, Nakanishi K, Watanabe N (1971) Electrochim Acta 16:1179CrossRefGoogle Scholar
  169. 169.
    Watanabe N (1983) J Fluorine Chem 22:205CrossRefGoogle Scholar
  170. 170.
    Tasaka A, Miki K, Yamaguchi S, Sato K (1993) Denki Kagaku 61:742Google Scholar
  171. 171.
    Wasser DJ, Johnson PS, Klink FW, Kucera F, Liu CC (1987) J Fluorine Chem 35:557CrossRefGoogle Scholar
  172. 172.
    Gambaretto GP, Napoli M, Conte L, Scipione A, Armelli R (1985) J Fluorine Chem 27:49CrossRefGoogle Scholar
  173. 173.
    Dimitrov A, Radeck W, Rüdiger S (1993) J Fluorine Chem 60:57CrossRefGoogle Scholar
  174. 174.
    Alsmeyer YW, Childs WV, Flynn RM, Moore GGI, Smeltzer JC (1994) in Electrochemical Fluorination and Its Applications in Banks RE et al. (eds) Organofluorine Chemistry: Principles and commercial Applications. Plenum Press, New York p 126Google Scholar
  175. 175.
    Meinert H (1994) Macromol Symp 82:201Google Scholar
  176. 176.
    Novak M, Boa J (1987) Stud Org Chem (Amsterdam) 30 (Recent Adv Electroorg Synth) 67; Chem Abs 108 (9) 74526WGoogle Scholar
  177. 177.
    Dimitrov A, Rüdiger S, Ignat’ev NV, Datsenko S (1990) J Fluorine Chem 50:197CrossRefGoogle Scholar
  178. 178.
    Hackerman N, Snavely ES, Fiel LD (1967) Electrochim Acta 12:535CrossRefGoogle Scholar
  179. 179.
    Novak M, Boa J (1980) Electroanal Chem 109:179CrossRefGoogle Scholar
  180. 180.
    Dimitrov A, Stewig H, Rüdiger S, Kolditz L (1990) J Fluorine Chem 47:13CrossRefGoogle Scholar
  181. 181.
    Dimitrov A, Rüdiger S, Bartoszek M (1990) J Fluorine Chem 47:23CrossRefGoogle Scholar
  182. 182.
    Dimitrov A, Rüdiger S, Ignatyev NV, Datcenko S (1990) J Fluorine Chem 50:197CrossRefGoogle Scholar
  183. 183.
    Dimitrov A, Radeck W, Rüdiger S, Bechstein O (1993) J Fluorine Chem 60:57CrossRefGoogle Scholar
  184. 184.
    Dimitrov A, Rüdiger S, Seppelt K, Peplinski T (1994) J Fluorine Chem 69:15CrossRefGoogle Scholar
  185. 185.
    Gross U, Rüdiger S, Dimitrov A (1996) J Fluorine Chem 76:139CrossRefGoogle Scholar
  186. 186.
    Sartori P, Ignat’ev N, Datsenko S (1995) J Fluorine Chem 75:157CrossRefGoogle Scholar
  187. 187.
    Zemva B, Chacon L, Lutar K, Shen C, Bartlett N (1994) 207th ACS Nat Meet, Div Fluorine Chem, San Diego CA; Zemva B, Chacon L, Lutar K, Fele-Beuermann M, Shen C, Allman J, Mònzenberg J, Bartlett N (1994) 14th Int Symp Fluorine Chem Yokohama Japan Paper 2 A 08Google Scholar
  188. 188.
    Bartlett N, Chambers RD, Roche AJ, Spink RCH, Chacon L, Whalen JM (1996) Chem Comm 1049Google Scholar
  189. 189.
    Zemva B, Slivnik J (1973) J Inorg Nucl Chem Supplement 1976:173Google Scholar
  190. 190.
    Chambers RD (1973) in Fluorine in Organic Chemistry, John Wiley & Sons, Inc. London p 30Google Scholar

Copyright information

© Springer Verlag Berlin Heidelberg 1997

Authors and Affiliations

  • Fred G. Drakesmith
    • 1
  1. 1.EA Technology Ltd.Capenhurst, ChesterUK

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