Syntheses with perfluoroalkyl radicals from perfluoroalkyl iodides. A rapid survey of synthetic possibilities with emphasis on practical applications. Part one: Alkenes, alkynes and allylic compounds

Journal of Fluorine Chemistry

Volumn 93, Issue 1, 1999, Pages 1-25

  Brace, Neal O ^a  

^a 2881 65th St N ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345770874     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(98)00255-3     Document Type: Review

References (124)

1. Dolbier W.R. Jr. Chem. Rev. 96:1996;1567-1584.
2. W.R. Dolbier Jr., Topics in Current Chemistry, vol. 192, Springer, Berlin/Heidelberg, Germany, 1997, pp. 97-163.
3. J.M. Hamilton Jr., TFE review, in: Advan. Fluorine Chem., vol. 3, Butterworth, Washington, DC, 1963, p. 147.
4. J.D. Hulbert, A.E. Feiring, Chem. Eng. News 75 (51) (1997) 6 (22 December 1997).
5. Simons J.H. The Simons cell. J. Electrochem. Soc. 95:1949;47.
6. D.D. Coffman, M. Raasch, et al. J. Org. Chem. (1949) 747.
7. H. Emeleus, R.N. Haszeldine, J. Chem. Soc. (London) (1949) 2948.
8. N.O. Brace, U.S. Patent 3 016 407, 9 Jan, 1962.
9. J.H. Simons, T.J. Brice, U.S. Patent 2 614 131 (1953), Chem. Abstr. 47 (1953) 8770c.
10. R.N. Haszeldine, K. Leedham, J. Chem. Soc. (London) (1953) 1548.
11. R.E. Parsons, U.S. Patent 3 283 020, Nov. 1, 1966.
12. R.E. Parsons, U.S. Patent 3 128 185, May 5, 1964.
13. Hauptschein M., Braid M. J. Am. Chem. Soc. 83:1961;2383.
14. R.D. Chambers, W.K.R. Musgrave, J. Savory, J. Proc. Chem. Soc. (1961) 113; J. Chem. Soc. (London) (1961) 3779.
15. R.D. Chambers, W.K.R. Musgrave, J. Savory, J. Proc. Chem. Soc. (1961) 113; J. Chem. Soc. (London) (1961) 3779.
16. R.E. Parsons, French Patent 1 385 682 (1965); Chem. Abstr. 47 (1953) 8770c.
17. R.E. Parsons, U.S. Patent 3 234 294, Feb. 8, 1966.
18. M. Haupstschein, U.S. Patent 3 006 973, October, 1961.
19. R.N. Haszeldine, J. Chem. Soc. (London) (1949) 2856.
20. R.N. Haszeldine, J. Chem. Soc. (London) (1953) 3761.
21. N.O. Brace, U.S. Patent 3 145 222, August, 1964.
22. T. Hayashi, M. Matsuo, U.S. Patent 4 001 309, January, 1977.
23. U. Schwenk, I. Koenig, A. Streitberger, U.S. Patent 4 219 681, August, 1980. Chem. Abstr. 93 (1980) 7656x.
24. K.K. Ray-Chaudhuri, C.P. Iovine, U.S. Patent 3 810 939, 1974.
25. J.-P. Lalu, L. Foulleteir, U.S. Patent 3 825 577, 1974.
26. W.S. Friedlander, U.S. Patent 3 088 849, May, 1963.
27. N.O. Brace, U.S. Patent 3 172 910, March, 1965, Chem. Abstr. 63 (1965) 5030.
28. R.I. Day, U.S. Patent 3 283 012, November, 1965.
29. Kharasch M.S., Jensen E.V., Urry W.H. Science. 102:1945;128.
30. FI adducts above 150°C gives HI which then cleaves EtOAc (or esters) to give EtI and RCOOH, thus removing the strongly acidic HI. Yield of product is increased and residue of tar is lessened.
31. 7I and 1,6-heptadiene cyclizes during the reaction, or by heating with more initiator.
32. 7I and cycohexene isomerizes by U.V. light to the equilibrium mixture.
33. N.O. Brace, J. Org. Chem. 37 (1972) 2429. (C5-C8 Cyclic alkenes).
34. N.O. Brace, J. Org. Chem. 27 (1962) 3033. Vinyl monomers.
35. 6 cyclic alkenes.
36. Brace, N.O. J. Org. Chem. 27 (1962) 3027. Bicyclic alkenes.
37. C. Walling, Review, in: Free Radicals in Solution, Wiley, New York, 1957, 175 pp.
38. C. Walling, Review, in: Free Radicals in Solution, Wiley, New York, 1957, 247 pp.
39. M. Hunt, U.S. Patent 2 471 959.
40. Overberger C.G.et al. J. Am. Chem. Soc. 71:1949;2661.
41. Overberger C.G.et al. J. Polymer Sci. 6:1951;539.
42. W.A. Pryor, Free Radicals, Chap. 10, McGraw-Hill, New York, 1966.
43. 1/2 in xylene at 80°C) of the three initiators are: 'Vazo 52' (AIVN), 17.9 min; 'Vazo 64' (AIBN), 75.5 min; 'Vazo 67' (AMBN), 116 min.
44. N.O. Brace, J. Org. Chem. 38 (1973) 3167. Terminal alkadienes.
45. Gale L.H. J. Org. Chem. 34:1969;81.
46. Sun Wei-C., Ng C-S., Prestwich G.D. J. Org. Chem. 571:1992;132.
47. R.N. Haszeldine, J. Chem. Soc. (London) (1952) 2504.
48. R.N. Haszeldine, B.R. Steele, J. Chem. Soc. (London) (1953) 1199.
49. R.N. Haszeldine, B.R. Steele, J. Chem. Soc. (London) (1954) 1923.
50. R.N. Haszeldine, B.R. Steele, J. Chem. Soc. (London) (1957) 2193.
51. R.N. Haszeldine, B.R. Steele, J. Chem. Soc. (London) (1957) 2800.
52. Park J.D., Larsen E.R., Holler H.V., Lacher J.R. J. Org. Chem. 23:1958;1166.
53. Henne A.L., Kraus D.W. J. Am. Chem. Soc. 76:1954;1175.
54. Henne A.L., Nager M. J. Am. Chem. Soc. 73:1951;5527.
55. C. Walling, Review, in: Free Radicals in Solution, Wiley, New York, 1957, 251 pp.
56. M. Knell, U.S. Patent 4 058 573, 15 Nov., 1977.
57. Brace N.O. J. Fluorine Chem. 62:1993;217.
58. N.O. Brace, J. Fluorine Chem. 70 (1995) 145. See corrigendum.
59. N.O. Brace, U.S. Patent 3 257 407, June 1966.
60. Brace N.O. J. Org. Chem. 27:1962;4491.
61. Santini G., Le Blanc M., Riess J.G. Tetrahedron. 29:1973;2411-2414.
62. Brace N.O., van Elswyk J.E. J. Org. Chem. 41:1976;766.
63. Brace N.O., Marshall L.W., Pinson C.J., van Wingerden G. J. Org. Chem. 49:1984;2361.
64. G. Van Dyke Tiers, J. Org. Chem. 27 (1962) 2261. Peroxide or U.V. light.
65. Brace N.O. J. Am. Chem. Soc. 86:1964;523.
66. Brace N.O. J. Org. Chem. 31:1966;2879.
67. Rabolt J.F., Russell T.P., Tweig R.J. Macromolecules. 17:1984;2786-2794.
68. Tweig R.J. Macromolecules. 21:1988;1806-1811.
69. Turberg M.P., Brady J.E. J. Am. Chem. Soc. 110:1988;7797-7801.
70. G.V.D. Tiers, U.S. Patent 2 951 051, August 1960.
71. Brace N.O. J. Org. Chem. 29:1964;1247.
72. Brace N.O. J. Org. Chem. 32:1967;430.
73. Brace N.O. J. Org. Chem. 36:1971;1904.
74. Hare E.F., Shafrin E.G., Zisman W.A. J. Phys. Chem. 58:1954;236.
75. Shafrin E.G., Zisman W.A. J. Phys. Chem. 66:1962;740.
76. M. Bernett, W.A. Zisman, J. Phys. Chem. 67 (1963) 1534. Many of these long chain acids were provided for this purpose by du Pont.
77. Naselli C., Swalen J.D., Rabolt J.F. J. Chem. Phys. 90(7):1989;3855.
78. R. Filler, Y. Kobayashi, L.M. Yagupolskii (Eds.), Biomedicinal Aspects of Fluorine Chemistry, Elsevier, Amsterdam, 1993.
79. J.T. Welch, S. Eswarakrischnan, Fluorine in Bioorganic Chemistry, Wiley, New York, 1991.
80. V.P. Kukhar, V.A. Soloshonok (Eds.), Fluorine Containing Amino Acids, Wiley, Chichester, 1995.
81. Soloshonok V.A., Soloshonok I.V., Kukhar V.P., Svedas V.K. J. Org. Chem. 63:1998;1878.
82. N.O. Brace, A.K. Mackenzie, U.S. Patent 3 083 224, March 1963.
83. nCOOH are dehalogenated and reduced to the alcohols.
84. Brace N.O. J. Fluorine Chem. 20:1982;313.
85. R. Fasick, S. Raynolds, U.S. Patent 3 282 905, November 1966.
86. N.O. Brace, J. Org. Chem. 60 (1995) 2059. See the footnotes 1-14 for references to work in this field.
87. L. Foulletier, J-P. Lalu, U.S. Patent 4 062 849, December 1977.
88. L. Foulletier, J-P. Lalu, French Patent 1 532 284, June 1968. Chem. Abstr. 71 (1969) 101289.
89. V. Bertocchio, L. Folletier, U.S. Patent 4 069 158, January 1978.
90. Milius A., Greiner J., Riess J.G. New J. Chem. 15:1991;337.
91. I. Ojima, J.R. McCarthy, J.T. Welch (Eds.), Biomedical Frontiers of Fluorine Chemistry, American Chemical Society, Washington, DC, 1996.
92. N.O. Brace, unpublished.
93. R.N. Haszeldine, J. Chem. Soc. (London) (1950) 3057.
94. R.N. Haszeldine, K. Leedham, J. Chem. Soc. (London) (1952) 3483.
95. Brace N.O. J. Org. Chem. 32:1967;2711.
96. 7I to allyl alcohol.
97. Prestwich G.D., Sun Wei-Chuan, Mayer M.S., Dickens J.C. J. Chem. Ecol. 16:1990;1761.
98. Sun Wei-Chuan, Prestwick G.D. Tetrahedron Lett. 31:1990;801.
99. Dawson G., Mudd A., Pickett J.A., Pile M.M., Wadhams L.J. J. Chem. Ecol. 16:1990;1779.
100. Brace N.O. J. Org. Chem. 44:1979;212.
101. Baum K., Bedford C.D., Hunadi R.J. J. Org. Chem. 47:1982;2251.
102. von Werner K. J. Fluorine Chem. 28:1985;229.
103. Fuchikami R., Ojima I. Tetrahedron Lett. 25:1984;303.
104. Takeyama T., Ichinose Y., Oshima K., Utimoto K. Tetrahedron Lett. 30:1989;3159.
105. C.Y. Meyers, W.S. Matthews, L.L. Ho, V.M. Kolb, T.E. Parady, in: G.V. Smith (Ed.), Catalysis in Organic Syntheses, Academic Press, New York, 1977, pp. 197-278.
106. C.Y. Meyers, in: M. Tisler (Ed.), Topics in Organic Sulfur Chemistry, University Press, Ljubljana, Yugoslavia, 1978, pp. 207-260.
107. D.H. Hua, Thesis, Southern Illinois University at Carbondale, Carbondale, IL 62901, 1979.
108. D.H. Hua, C.Y. Meyers, Abstracts, no 196, 197, Midwest Regional ACS Meeting, Rockford, IL, 1979.
109. Zwiefel G., Murray R.E., On H.P. J. Org. Chem. 46:1981;1292.
110. Brace N.O. J. Org. Chem. 40:1975;851.
111. Zarif L., Greiner J., Pace S., Riess J.G. J. Med. Chem. 33:1990;1262.
112. M. Knell, N.O. Brace, U.S. Patent 3 843 735, October 1974.
113. Bartlett P.D., Altschul R. J. Am. Chem. Soc. 67:1945;812.
114. C. Walling, Free Radicals in Solution, Wiley, New York, 1957, 259 pp.
115. 7I to allyl alcohol and allyl chloride. J. Chem. Eng. Data. 9:1964;251.
116. 2 in 61% yield.
117. T. Deisenroth, R. Falk, J. Haase, U.S. Patent 5 585 517, Dec. 17, 1996.
118. M. Haniff, R. Falk, T. Deisenroth, K.F. Mueller, U.S. Patent 5 491 261, Feb. 13, 1996.
119. Huang W.Y. J. Fluorine Chem. 58:1992;1.
120. Rong G.B., Keese R. Tetrahedron Lett. 39:1990;5615.
121. Nguyen B.V., Yang Z.-Y., Burton D.J. J. Org. Chem. 63:1998;2887.
122. K.C. Smeltz, U.S. Patent 3 478 116, March 1969.
123. K.C. Smeltz, U.S. 3 504 016, March 1970.
124. W.R. Remingtion, U.S. Patent 4 346 141, August 1982.