Abstract
The physical properties and chemical reactivities of organic molecules can be dramatically affected by fluorination. Today’s diverse commercial applications of organo-fluorine materials clearly manifest the possible beneficial effects of fluorination, and the numerous ways in which industry has taken practical advantage of these effects are the subjects of the following chapters in this book. This chapter focuses on the characteristic substituent effects that underlie the physicochemical properties of organofluorine compounds, especially those important to the design of commercial products. Fortunately, advances in both experimental and theoretical physical organofluorine chemistry over the past two decades have made the “unusual” behavior of fluorinated compounds much more understandable and predictable. General principles that govern the characteristic effects of fluorination will be presented, but important exceptions also will be noted. Misleading generalizations like “fluorination increases lipophilicity” and myths about fluorine steric effects will be dispelled, for example.
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References
K. D. Sen and C. K. Jorgensen, Electronegativity, Springer-Verlag, New York (1987).
J. K. Nagel, J. Am. Chem. Soc. 112, 4740 (1990).
L. C. Allen, D. A. Egolf, E. T. Knight, and C. Liang, J. Phys. Chem. 94, 5602 (1990).
A. Bondi, J. Phys. Chem. 68, 441 (1964).
A. Maciejewski, J. Photochem. Photobio., A: Chemistry 51, 87 (1990).
T. M. Reed III, in: Fluorine Chemistry (J. H. Simons, ed.), Vol. 5, Chapter 2, Academic Press, New York (1964)
H. G. Bryce, in: ibid., Vol. 5, Chapter 4 (1964)
T. J. Brice, in: ibid., Vol. 1, Chapter 13 (1950).
D. S. L. Slinn and S. W. Green, in: Preparation, Properties, and Industrial Applications of Organofluorine Compounds (R. E. Banks, ed.), Chapter 2, Ellis Horwood, Chichester (1982).
W. Mahler (DuPont), personal communication.
C. R. Patrick, in: Preparation, Properties, and Industrial Applications of Organofluorine Compounds (R. E. Banks, ed.), Chapter 10, Ellis Horwood, Chichester (1982).
D. F. Persico, H.-N. Huang, R. J. Lagow, and L. C. Clark, Jr., J. Org. Chem. 50, 5156 (1985).
R. D. Nelson, Jr., D. R. Lide, Jr., and A. A. Maryott, Selected Values of Electric Dipole Moments in the Gas Phase, NSRD-NBS 10, Government Printing Office, Washington, DC (1967)
A. L. McClellan, Tables of Experimental Dipole Moments, Vol. 1, W. H. Freeman, San Francisco (1963).
M. Hudlicky, Chemistry of Organofluorine Compounds, 2nd edn., Chapter 7, Wiley, New York (1976)
W. A. Sheppard and C. M. Sharts, Organic Fluorine Chemistry, pp. 17, 42-43, W. A. Benjamin, New York (1969).
A. M. Lovelace, D. A. Rausch, and W. Postelnek, Aliphatic Fluorine Compounds, Reinhold, New York (1958).
V. Majer and V. Svoboda, Enthalpies of Vaporization of Organic Compounds, Blackwell, Boston (1985).
J. S. Chickos, in: Molecular Structure and Energetics (J. F. Liebman and A. Greenburg, eds.), Vol. 2, VCH Publishers, New York (1987).
A. J. Lovinger, Science 220, 1115 (1983)
A. J. Lovinger, in: Developments in Crystalline Polymers (D. C. Bassett, ed.), Applied Science Publishers, London (1982).
J. A. Dean (ed.), Lange’s Handbook of Chemistry, 13th edn., McGraw-Hill, New York (1985).
S. Wu, Polymer Interface and Adhesion, Marcel Dekker, New York (1982).
A. G. Pittman, in: Fluoropolymers (L. A. Wall, ed.), High Polymers Vol. XXV, Chapter 13, Wiley, New York (1972).
E. F. Hare, E. G. Shafrin, and W. A. Zisman, J. Colloid. Sci. 58, 236 (1954).
N. Watanabe, T. Nakajima, and H. Touhara, Graphite Fluorides, Studies in Inorganic Chemistry 8, Elsevier, Oxford (1988).
M. M. Doeff and E. Lindler, Macromolecules 22, 2951 (1989).
A. J. Arduengo, III, J. R. Moran, J. Rodriguez-Parada, and M. D. Ward, J. Am. Chem. Soc. 112, 6153 (1990).
A. Sekiya and M. Tamura, Chem. Lett. 707 (1990).
J. Schneider, C. Erdelen, H. Ringsdorf, and J. F. Rabolt, Macromolecules 22, 3475 (1989)
S. G. Wolf, M. Deutsch, E. M. Landau, M. Lahav, L. Leiserowitz, K. Kjaer, and J. Als-Nielsen, Science 242, 1286 (1988)
I. Weissbuch, F. Frolow, L. Addadi, M. Lahav, and L. Leiserowitz, J. Am. Chem. Soc. 112, 7718 (1990).
K. Shinoda, M. Hato, and T. Hayaski, J. Phys. Chem. 76, 909 (1972).
H. Kuneida and K. Shinoda, J. Phys. Chem. 80, 2468 (1976)
W. Guo, T. A. Brown, and B. M. Fung, J. Phys. Chem. 95, 1829 (1991).
G. Mathis, P. Leempoel, J.-C. Ravey, C. Selve, and J.-J. Delpuech, J. Am. Chem. Soc. 106, 6162 (1984)
L. Matos, J.-C. Ravey, and G. Serratrice, J. Colloid. Interface Sci. 128, 341 (1989)
C. Selve, J.-C. Ravey, M.-J. Stebe, C. E. Moudjahid, and J.-J. Delpuech, Tetrahedron 47, 411 (1991).
M. Miyamoto, K. Aoi, and T. Saegusa, Macromolecules 22, 3540 (1989).
C. Selve, E. M. Moumni, J.-J. Delpuech, J. Chem. Soc, Chem. Commun. 1437 (1987).
I. Rico, A. Lattes, K. P. Das, and B. Lindman, J. Am. Chem. Soc. 111, 7267 (1989).
T. P. Russell, J. F. Rabolt, R. J. Twieg, R. L. Siemens, and B. L. Farmer, Macromolecules 19, 1135 (1986)
R. J. Twieg, T. P. Russell, R. Siemens, and J. F. Rabolt, Macromolecules 18, 1361 (1985).
M. P. Turnberg and J. E. Brady, J. Am. Chem. Soc. 110, 7797 (1988).
G. Martini, M. F. Ottaviani, S. Ristori, D. Lenti, and A. Sanguined, Colloids Surf. 45, 177 (1990).
K. Kalyanasundaram, Langmuir 4, 942 (1988).
N. Muller and R. H. Birkhahn, J. Phys. Chem. 71, 957 (1967).
S. S. Berr and R. R. M. Jones, J. Phys Chem. 93, 2555 (1989).
S. J. Burkitt, R. H. Ottewill, J. B. Hayter, and B. T. Ingram, Colloid Polym. Sci. 265, 619 (1987).
S. J. Burkitt, R. H. Ottewill, J. B. Hayter, and B. T. Ingram, Colloid Polym. Sci. 265, 628 (1987).
H. Hoffman, J. Klaus, K. Reizlein, W. Ulbricht, and K. Ibel, Colloid Polym. Sci. 260, 435 (1982).
R. Elbert, T. Folda, and H. Ringsdorf, J. Am. Chem. Soc. 106, 7687 (1984)
T. Kunitake, Y. Okahata, and S. Yasunami, J. Am. Chem. Soc. 104, 5547 (1982).
W. P. Zhang and D. L. Dorset, Macromolecules 23, 4322 (1990)
C. W. Bunn and E. R. Howells, Nature 174, 549 (1954)
E. S. Clark and L. T. Muus, Z Kristallogr. 117, 119 (1962).
C. Naselli, J. D. Swalen, and J. F. Rabolt, J. Chem. Phys. 90, 3855 (1989).
D. A. Dixon and F. A. Van Catledge, Int. J. Supercomputer Appl. 2, 62 (1988)
D. A. Dixon, F. A. Van-Catledge, and B. E. Smart, Abstracts of the 9th IUPAC Conf on Phys. Org. Chem. A15 (1988).
D. F. Eaton and B. E. Smart, J. Am. Chem. Soc. 112, 2821 (1990).
R. J. Twieg and J. F. Rabolt, J. Polym. Sci., Polym. Phys. Ed. 21, 901 (1983).
R. J. Twieg and J. F. Rabolt, Macromolecules 21, 1806 (1988).
J. Höpken and M. Möller, Macromolecules 25, 2482 (1992)
W. Mahler, D. Guillon, and A. Skoulios, Mol. Cryst. Liq. Cryst., Lett. Sect. 2, 111 (1985).
F. Tournilhac, L. Bosio, J. F. Nicoud, and J. Simon, Chem. Phys. Lett. 145, 452 (1988).
A. E. Feiring, in: Frontiers of Macromolecular Science (T. Saegusa, T. Higashimura, and A. Abe, eds.), Blackwell, Oxford (1989).
A. M. F. Barton, Handbook of Solubility Parameters and Other Cohesive Parameters, CRC Press, Boca Raton (1983).
R. Fusch, E. J. Chambers, and W. K. Stephenson, Can. J. Chem. 65, 2624 (1987)
R. Fusch, L. A. Peacock, and K. Das, Can. J. Chem. 58, 2301 (1980).
J. H. Hildebrand, J. M. Prausnitz, and R. L. Scott, Regular and Related Solutions, Van Nostrand-Reinhold, New York (1970)
J. S. Rowlinson and F. L. Swinton, Liquids and Liquid Mixtures, 3rd edn., Butterworth, London (1982).
T. Handa and P. Mukerjee, J. Phys. Chem. 85, 3916 (1981)
P. Mukerjee, A. Y. S. Yang, J. Phys. Chem. 80, 1388 (1976)
J. Carlfors and P. Stibbs, J.Phys. Chem. 88, 4410 (1984).
D. L. Dorset, Macromolecules 23, 894 (1990).
C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd edn., VCH Publishers, New York (1988).
B. K. Freed, J. Biesecker, and W. J. Middleton, J. Fluorine Chem. 48, 63 (1990).
R. Battino and H. L. Clever, Chem. Rev. 66, 395 (1966)
E. Wilhelm and R. Battino, Chem. Rev. 73, 11 (1973).
M’H. A. Hamza, G. Serratrice, M.-J. Stébé, and J. J. Delpuech, J. Am. Chem. Soc. 103, 3733 (1981).
H. G. Mack and H. Oberhammer, J. Chem. Phys. 87, 2158 (1987)
S. Oikawa, M. Tsuda, and N. Nagayama, Theor. Chim. Acta 64, 403 (1984).
J. Afzal, S. R. Ashlock, B. M. Fung, and E. A. O’Rear, J. Am. Chem. Soc. 90, 3019 (1986).
G. Serratrice, J. J. Delpuech, and R. Diguet, Nouv. J. Chem. 6, 489 (1982).
C. Hansch and A. Leo, Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley, New York (1979).
T. Fujita, Prog. Phys. Org. Chem. 14, 75 (1983).
J. Sangster, J. Chem. Phys. Ref. Data 18, 3 (1989).
A. E. Feiring and B. E. Smart, in: Ullmann’s Encyclopedia of Industrial Chemistry, Vol. A11, pp. 367–370, VCH Publishers, New York (1988).
N. Müller, J. Pharm. Sci. 75, 987 (1986).
L. M. Yagupol’skii, A. Ya. Il’chenko, and N. V. Kondratenko, Russ. Chem. Rev. 43, 32 (1974).
L. M. Yagupol’skii, J. Fluorine Chem. 36, 1 (1987).
M. H. Abraham, P. L. Grellier, D. V. Prior, P. P. Duce, J. J. Morris, and P. J. Taylor, J. Chem. Soc, Perkin Trans. 2, 699 (1989).
M. H. Abraham, P. L. Grellier, D. V. Prior, J. J. Morris, and P. J. Taylor, J. Chem. Soc, Perkin Trans. 2, 521 (1990).
J. M. Birchall and R. M. Haszeldine, J. Chem. Soc. 3653 (1959).
J. Hine, S. Hahn, and J. Hwang, J. Org. Chem. 53, 884 (1988).
J. M. Carpentier, F. Ferner, R. Schall, N. V. Ignatev, V. N. Boiko, and L. M. Yagupol’skii, Bull Soc. Chim. Fr. 150 (1985).
J. Foropoulous, Jr. and D. D. DesMarteau, Inorg. Chem. 23, 3720 (1984).
R. J. Koshhar and R. A. Mitsch, J. Org. Chem. 38, 3358 (1973).
G. Klöter, H. Pritzkow, and K. Seppelt, Angew Chem., Int. Ed. Engl. 19, 942 (1980).
R. J. Gillespie and J. Liang, J. Am. Chem. Soc. 110, 6053 (1988).
G. A. Olah, G. K. S. Prakash, and J. Sommer, Superacids, Wiley, New York (1985).
D. Moutz and K. Bartmann, Angew. Chem., Int Ed., Engl. 27, 391 (1988).
P. J. Stang, M. Hanak, and L. R. Subramanian, Synthesis 85 (1982)
F. Effenberger, Angew Chem., Int. Ed. Engl. 19, 751 (1980).
D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution, Butterworths, London (1965), Suppl. (1972).
R. Filler, Fluorine Chem. Rev. 8, 1 (1977).
R. E. Banks, Fluorocarbons and Their Derivatives, Macdonald, London (1970).
J. F. Liebman, in: Fluorine Containing Molecules (J. F. Liebman, A. Greenberg, and W. R. Dolbier, Jr., eds.), VCH Publishers, New York (1988)
R. W. Taft, Prog. Phys. Org. Chem. 14, 247 (1983).
G. A. Olah and Y. R. Mo, Adv. Fluorine Chem. 7, 69 (1973).
M. Goodman, I. G. Rosen, and M. Safdy, Biopolymers 2, 503, 519, 537 (1964)
W. J. Middleton, U.S. Patent 3, 418, 337 (to DuPont) [CA 60, 7000 (1964)].
T. W. Bentley, C. T. Bowen, D. H. Morten, and P. v. R. Schleyer, J. Am. Chem. Soc. 103, 5466 (1981)
T. W. Bentley and G. E. Carter, J. Am. Chem. Soc. 104, 5741 (1982).
A. L. Brown, Y. Chiang, A. J. Kresge, Y. S. Tang, and W.-H. Wang, J. Am. Chem. Soc. 111, 4918 (1989).
C. Sandorfy, R. Buchet, L. S. Lussier, P. Ménassa, and L. Wilson, Pure Appl. Chem. 58, 1115 (1986).
P. Hobza, F. Mulder, and C. Sandorfy, J. Am. Chem. Soc. 104, 925 (1982).
A. A. Hasanein, J. Comput. Chem. 5, 528 (1984)
A. Popowicz and T. Ishida, Chem. Phys. Lett. 83, 520 (1981).
C. A. Deakyne and M. Meot-Ner Mautner, J. Am. Chem. Soc. 107, 474 (1985).
J. Huang and K. Hedberg, J. Am. Chem. Soc. 111, 6909 (1989)
D. A. Dixon and B. E. Smart, in: Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456 (J. T. Welch, ed.), American Chemical Society, Washington, D.C. (1991).
W. Caminati, J. Mol Spectrosc. 92, 101 (1982).
J.-M. Dumas, M. Gomel, and M. Guerin, in: The Chemistry of Functional Groups, Supplement D (S. Patai and Z. Rappoport, eds.), Chapter 21, Wiiey, Chichester (1983).
G. A. Crowder, J. Fluorine Chem. 14, 11 (1979).
D. Christen, D. Damiani, and D. G. Lister, J. Mol. Struct. 41, 315 (1977).
P. Murray-Rust, W. C. Stallings, C. T. Monti, R. K. Preston, and J. P. Glusker, J. Am. Chem. Soc. 105, 3206 (1983).
A. N. Chekhlov, V. L. Fetisov, S. I. Kolbasenko, and I. V. Martynov, Dokl. Akad. Nauk SSSR 297, 1177(1987).
B. E. Smart, in: Molecular Structure and Energetics (J. F. Liebman and A. Greenberg, eds.), Vol. 3, Chapter 4, VCH Publishers, Deerfield Beach, FL (1986).
R. E. Banks and J. C. Tatlow, in: Fluorine: The First Hundred Years (1886–1986) (R. E. Banks, D. W. A. Sharp, and J. C. Tatlow, eds.), Chapter 11, Elsevier, New York (1986).
B. E. Smart, in: The Chemistry of Functional Groups, Supplement D, Part 2 (S. Patai and Z. Rappoport, eds.), Chapter 14, Wiley, New York (1983).
J. F. Liebman, A. Greenberg, and W. R. Dolbier, Jr. (eds.), Fluorine Containing Molecules, VCH Publishers, New York (1988).
M. Hudlický, Chemistry of Organofluorine Compounds, Ellis Horwood, Chichester (1976).
R. D. Chambers, Fluorine in Organic Chemistry, Wiley, New York (1973).
D. F. McMillen and D. M. Golden, Ann. Rev. Phys. Chem. 33, 493 (1982).
S. K. Shin and J. L. Beauchamp, J. Am. Chem. Soc. Ill, 900 (1989).
H. F. Koch, Acc. Chem. Res. 17, 137 (1984)
C. J. Stirling, Acc. Chem. Res. 12, 198 (1974)
R. E. Parker, Adv. Fluorine Chem. 3, 63 (1963).
C. G. Swain and R. E. T. Spalding, J. Am. Chem. Soc. 82, 6104 (1960).
M. Namavari, N. Satayamurthy, M. E. Phelps, and J. R. Barrio, Tetrahedron Lett. 31, 4973 (1990).
S. S. Szucs, Chem. Eng. News 68, 4 (1990).
D. Griller, J. M. Kanabus-Kaminska, and A. Maccol, J. Mol. Struct. (Theochem) 163, 125 (1988).
J. A. Seetula, J. J. Russell, and D. Gutman, J. Am. Chem. Soc. 112, 1347 (1990).
B. S. Evans, I. Weeks, and E. Whittle, J. Chem. Soc, Faraday Trans. 1, 79, 147 (1983).
F. G. Bordwell and W. Brannen, Jr., J. Am. Chem. Soc. 86, 4645 (1964).
C. Wakselman, J. Fluorine Chem. 59, 367 (1992)
C. Wakselman and C. Kaziz, in: Fluorine: The First Hundred Years (1886–1986) (R. E Banks, D. W. A. Sharp, and J. C. Tatlow, eds.), Chapter 12, Elsevier, New York (1986).
A. E. Feiring, J. Org. Chem. 50, 3269 (1985)
A. E. Feiring, J. Org. Chem. 48, 347 (1983).
J. F. Liebman, W. R. Dolbier, Jr., and A. Greenberg, J. Phys. Chem. 90, 394 (1986).
M. M. Rahman, B. A. Secor, K. M. Morgan, P. R. Schafer, and D. M. Lemal, J. Am. Chem. Soc. 112, 5986 (1990).
L. A. Wall, in: Fluoropolymers (L. A. Wall, ed.), High Polymers Vol. XXV, Chapter 12, Wiley, New York (1972).
J. N. Butler, J. Am. Chem. Soc. 84, 1393 (1962).
M. J. Birchall, R. Fields, R. N. Haszeldine, and R. J. McClean, J. Fluorine Chem. 15, 487 (1980).
R. C. Kennedy and J. B. Levy, J. Fluorine Chem. 7, 101 (1976)
W. Mahler and P. R. Resnick, J. Flourine Chem. 3, 451 (1973).
H. Millauer, W. Schwertfeger, and G. Siegemund, Angew. Chem., Int Ed. Engl. 24, 161 (1985)
P. Tarrant, C. G. Allison, K. P. Barthold, and E. C. Stump, Jr., Fluorine Chem. Rev. 5, 77 (1971).
V. Aviyente and Y Inel, Can. J. Chem. 68, 1332 (1990).
A. J. Dias and T. J. McCarthy, Macromolecules 17, 2529 (1984)
J. V. Brennan and T. J. McCarthy, Polym. Prep., Am. Chem. Soc, Div. Polym. Chem. 29, 338 (1988).
C. Y Wang and J. A. Tarter, Anal Chem. 55, 1775 (1983)
L. Kavan, F. P. Dousek, and K. Micka, J. Phys. Chem. 94, 5127 (1990).
R. C. Benning and T. J. McCarthy, Macromolecules 23, 2648 (1990)
S. B. Dake, S. V. Bhoraskar, S. V. Patil, and N. S. Narashiman, Polymer 27, 910 (1986).
C. A. Costello and T. J. McCarthy, Macromolecules 20, 2819 (1987).
A.A. Christodoulides, D. L. McCorkle, and L. G. Christophorou, in: Electron Molecule Interactions and Their Applications (K. G. Christophorou, ed.), Academic, New York (1984)
P. Kebarle and S. Chowdhury, Chem. Rev. 87, 513 (1987).
S. M. Spyrou, S. R. Hunter, and L. G. Christophorou, J. Chem. Phys. 83, 641 (1985).
A. Hasegawa, M. Shiotani, and F. Williams, J. Chem. Soc, Faraday Discuss. 63, 157 (1977)
M. Hasegawa and F. Williams, Chem. Phys. Leff. 45, 275 (1977).
D. D. MacNicol and C. D. Robertson, Nature (London) 332, 59 (1988).
D. L. Cooper, N. L. Allan, and R. L. Powell, J. Fluorine Chem. 49, 421 (1990)
J. A. Marsella, A. G. Gilicinski, A. M. Coughlin, and G. P. Pez, J. Org. Chem. 57, 2856 (1992).
S. Y Wang and W. T. Borden, J. Am. Chem. Soc. 111, 7282 (1989).
J. M. Pickard and A. S. Rodgers, J. Am. Chem. Soc 99, 695 (1977).
E. C. Wu and A. S. Rodgers, J. Am. Chem. Soc. 98, 6112 (1976).
D. A. Dixon and B. E. Smart, J. Phys. Chem. 93, 7772 (1989).
M. I. Bruce and W. R. Cullen, Fluorine Chem. Rev. 4, 79 (1969).
W. H. Sharkey, Fluorine Chem. Rev. 2, 1 (1969)
P. D. Bartlet, Quart. Rev. 24, 473 (1970).
L. Batt and R. Walsh, Int. J. Chem. Kinet. 14, 933 (1982).
B. D. Song and W. P. Jencks, J. Am. Chem. Soc. 111, 8470, 8479 (1989).
F. E. Rogers and R. J. Rapiejko, J. Am. Chem. Soc. 93, 4596 (1971).
C. G. Krespan and W. J. Middleton, Fluorine Chem. Rev. 1, 145 (1967)
W. J. Middleton, in: Kirk Othmer: Encyclopedia of Chemical Technology, Vol. 10, Wiley, New York (1980).
A. Greenberg, J. F. Liebman, and D. van Vechten, Tetrahedron 36, 1161 (1980).
D. M. Lemal and L. H. Dunlap, J. Am. Chem. Soc. 94, 6562 (1972).
Y. Kobayashi and I. Kumadaki, Top. Curr. Chem. 123, 103 (1984).
W. J. Feast and J. N. Winter, J. Chem. Soc, Chem. Commun. 202 (1985).
R. J. Blint, T. B. McMahon, and J. L. Beauchamp, J. Am. Chem. Soc. 96, 1269 (1974).
A. D. Williams, P. R. LeBreton, and J. L. Beauchamp, J. Am. Chem. Soc. 98, 2705 (1976).
G. A. Olah and Y. K. Mo, in: Carbonium Ions (G. A. Olah and P. v. R. Schleyer, eds.), Vol. V, Chapter 36, Wiley, New York (1976).
G. A. Olah and Y. K. Mo, Adv. Fluorine Chem. 7, 69 (1973).
R. W. Taft, R. H. Martin, and F. W. Lampe, J. Am. Chem. Soc. 87, 2490 (1965).
P. E. Peterson, R. J. Bopp, and M. M. Ajo, J. Am. Chem. Soc. 92, 2834 (1970).
A. D. Allen and T. T. Tidwell, J. Am. Chem. Soc. 104, 3145 (1982).
W. J. Johnson, G. W. Daub, T. A. Lyle, and M. Niwa, J. Am. Chem. Soc. 102, 7802 (1980).
G. Modena and G. Scorrano, in: The Chemistry of the Carbon-Halogen Bond (S. Patai, ed.), Chapter 6, Wiley, London (1973).
X. Creary, Chem. Rev. 91, 1625 (1991)
A. D. Allen and T. T. Tidwell, in: Advances in Carbocation Chemistry (X. Creary, ed.), Chapter 1, JAI Press, Greenwich (1989).
G. P. Ford and K. S. Raghuveer, Tetrahedon 44, 7489 (1988).
G. F. Koser, in: The Chemistry of Functional Groups; Supplement D, Part 2 (S. Patai and Z. Rappoport, eds.), Chapter 25, Wiley, New York (1983).
G. A. Olah, G. K. S. Prakash, and V. V. Krishnamurthy, J. Org. Chem. 48, 5116 (1983).
F. Cacace, Acc. Chem. Res. 21, 215 (1988).
V. Nguyen, X. Cheng, and T. H. Morton, J. Am. Chem. Soc. 114, 7127 (1992).
D. A. Stams, T. D. Thomas, D. C. MacLaren, D. Ji, and T. H. Morton, J. Am. Chem. Soc. 112, 1427 (1990).
P. C. Myhre and G. D. Andrews, J. Am. Chem. Soc. 92, 7595, 7596 (1970).
B. L. Dyatkin, E. P. Mochalina, and I. L. Knunyants, Fluorine Chem. Rev. 3, 45 (1969)
G. G. Belen’kii and L. S. German, in: Soviet Scientific Reviews, Section B, Chemistry Reviews, Vol. 5 (M. E. Vol’pin, ed.), pp. 183–218, Ellis Horwood, London (1984).
G. G. Yakobson and G. G. Furin, in: Soviet Scientific Reviews, Section B, Chemistry Reviews, Vol. 5 (M. E. Vol’pin, ed.), pp. 255–296, Ellis Horwood, London (1984).
K. M. Koshy, D. Roy, and T. T. Tidwell, J. Am. Chem. Soc. 101, 357 (1979).
W Kirmse, U. Mrotzeck, and R. Siegfried, Angew. Chem., Int. Ed. Engl. 24, 55 (1985).
V. Kanagasabapathy, J. F. Sawyer, and T. T. Tidwell, J. Org. Chem. 50, 503 (1985).
A. J. Kirby, H. Ryder, and V. Matassa, J. Chem. Soc, Perkin Trans. 2, 825 (1990).
J. Fried, E. A. Hallinan, and M. J. Swedo, Jr., J. Am. Chem. Soc. 106, 3871 (1984).
J. Fried, V. John, M. J. Swedo, Jr., C. K. Chen, C. O. Yang, T. A. Morinelli, A. K. Okwu, and P. V. Halushka, J. Am. Chem. Soc. 111, 4510 (1989).
I. L. Knunyants and G. A. Sokolski, Angew Chem., Int Ed. Engl. 11, 583 (1972).
O. Paleta, Fluorine Chem. Rev. 8, 39 (1977).
R. D. Chambers and M. R. Bryce, in: Comprehensive Carbanion Chemistry, Part C (E. Buncel and T. Durst, eds.), Chapter 5, Elsevier, Amsterdam (1987).
O. A. Reutov, I. P. Beletskaya, and K. P. Butin, CH-Acids, Pergamon, Oxford (1978).
A. Streitwieser, Jr., D. Holtz, G. R. Ziegler, J. O. Stoffer, M. L. Brokaw, and F. Guibe, J. Am. Chem. Soc. 98, 5229 (1976).
D. S. Marynick, J. Mol. Struct. 87, 161 (1982).
D. A. Dixon, T. Fukunaga, and B. E. Smart, J. Phys. Org. Chem. 1, 153 (1988)
J. H. Hammons, D. A. Hrovat, and W. T. Borden, J. Phys. Org. Chem. 3, 635 (1990).
A. E. Reed and P. v. R. Schleyer, J. Am. Chem. Soc. 112, 1434 (1990): D. A. Dixon, T. Fukunaga, and B. E. Smart, J. Am. Chem. Soc. 108, 4027 (1986)
D. S. Friedman, M. M. Francl, and L. C. Allen, Tetrahedron 41, 499 (1985).
J. H. Sleigh, R. Stephens, and J. C. Tatlow, J. Fluorine Chem. 15, 411 (1980).
W. B. Farnham, B. E. Smart, W. J. Middleton, J. C. Calabrese, and D. A. Dixon, J. Am. Chem. Soc. 107, 4565 (1985).
W. B. Farnham, D. A. Dixon, and J. C. Calabrese, J. Am. Chem. Soc. 110, 2607 (1988).
E. D. Laganis and D. M. Lemal, J. Am. Chem. Soc. 102, 6633 (1980).
G. Paprott and K. Seppelt, J. Am. Chem. Soc. 106, 4060 (1984).
A. E. Bayliff and R. D. Chambers, J. Chem. Soc, Perkin Trans. 1 201 (1988)
B. E. Smart, W. J. Middleton, and W. B. Farnham, J. Am. Chem. Soc. 108, 4905 (1986).
W. B. Farnham, W. J. Middleton, W. C. Fultz, and B. E. Smart, J. Am. Chem. Soc. 108, 3125 (1986).
D. A. Dixon, W. B. Farnham, and B. E. Smart, Inorg. Chem. 29, 3954 (1990).
B. E. Smart and W. J. Middleton, J. Am. Chem. Soc. 109, 4982 (1987).
R. D. Chambers and R. H. Mobbs, Adv. Fluorine Chem. 4, 50 (1965).
J. D. Park, R. J. McMurtry, and J. H. Adams, Fluorine Chem. Rev. 2, 55 (1968).
H. F. Koch, in: Comprehensive Carbanion Chemistry (E. Buncel and T. Durst, eds.), Chapter 6, Elsevier, Amsterdam (1987)
F. Koch and J. G. Koch, in: Fluorine-Containing Molecules (J. F. Liebman, A. Greenberg, and W. R. Dolbier, Jr., eds.), Chapter 6, VCH Publishers, New York (1988).
Z. Rappoport, Adv. Phys. Org. Chem. 7, 1 (1969).
C. G. Krespan, F. A. Van Catledge, and B. E. Smart, J. Am. Chem. Soc. 106, 5544 (1986)
C. G. Krespan and B. E. Smart, J. Org. Chem. 51, 320 (1986).
J. R. Gandler, J. W. Storer, and D. A. A. Ohlberg, J. Am. Chem. Soc. 112, 7756 (1990).
R. J. dePasquale and C. Tamborski, J. Org. Chem. 32, 2163 (1967).
P. P. Rodinov and G. G. Furin, J. Fluorine Chem. 47, 361 (1990)
L. S. Kobrina, Fluorine Chem. Rev. 7, 1 (1974).
D. J. Pasto, R. Krasnansky, and C. Zercher, J. Org. Chem. 52, 3062 (1987).
H. G. Viehe, Z. Janousek, and R. Merenyi (eds.), Substituent Effects in Radical Chemistry, Reidel, Dordrecht (1986)
L. Kaplan, Bridged Free Radicals, Marcel Dekker, New York (1972).
X.-K Jiang and G.-Z. Ji, J. Org. Chem. 57, 6051 (1992)
J. M. Dust and D. R. Arnold, J. Am. Chem. Soc. 105, 1221 (1983).
G. Leroy, D. Peeters, and C. Wilante, J. Mol Struct. 88, 217 (1982).
J. M. Tedder, Angew. Chem., Int. Ed. Engl. 21, 401 (1982)
J. M. Tedder and J. C. Walton, Adv. Phys. Org. Chem. 16, 51 (1978).
P. S. Skell and K. J. Shea, Israel J. Chem. 10, 493 (1972).
E. Tschuikow-Roux, T. Yano, and J. Niedzielski, J. Chem. Phys. 82, 65 (1985).
R. Atkinson, Chem. Rev. 85, 69 (1985)
R. Liu, R. E. Huie, and M. J. Kurylo, J. Phys. Chem. 94, 3247 (1990).
N. Cohen and S. W. Benson, J. Phys. Chem. 91, 162, 171 (1987).
J. M. Tedder and J. C. Walton, Adv. Free Radical Chem. 6, 155 (1980).
J. F. Harris and F. W. Stacey, J. Am. Chem. Soc. 83, 840 (1961).
M. Kotaka, T. Kohida, and S. Sato, Z. Naturforsch. B, Chem. Sci. 45, 721 (1990).
G. O. Pritchard, S. H. Abbas, J. M. Kennedy, S. J. Paquette, D. B. Hudson, M. A. Meleason, and D. D. Shoemaker, Int. J. Chem. Kinet. 22, 1051 (1990).
E. A. Carter and W A. Goddard, III, J. Chem. Phys. 88, 1752 (1988)
D. A. Dixon, J. Phys. Chem. 90, 54 (1986).
D. J. Burton and J. L. Hanfeld, Fluorine Chem. Rev. 8, 119 (1977)
R. A. Moss, in: Carbenes (R. A. Moss and M. Jones, Jr., eds.), Vol. I, Wiley, New York (1973).
R. A. Moss, Acc. Chem. Res. 22, 15 (1989); 13, 58 (1980).
B. Giese, W.-B. Lee, and J. Meister, Ann. Chem. 725 (1980).
P. B. Chinoy and P. D. Sunavala, Ind. Eng. Chem. Res. 26, 1340 (1987).
D. E. Williams and D. J. Houpt, Acta Cryst. B42, 286 (1986).
C. W. Thornber, Chem. Soc. Rev 8, 563 (1979).
T. Schaefer, R. P. Veregin, R. Laatikainen, R. Sebastian, K. Marat, and J. L. Chareton, Can. J. Chem. 60, 2611 (1982).
R. Cosmo and S. Sternhell, Aust. J. Chem. 40, 35 (1987).
G. Bott, L. D. Field, and S. Sternhell, J. Am. Chem. Soc. 102, 5618 (1980).
S. A. Sherrod, R. L. daCosta, R. A. Barnes, and V. Boekelheide, J. Am. Chem. Soc. 96, 1565 (1974).
B. E. Smart, J. Org. Chem. 38, 2027, 2035, 2039 (1973).
J. Hirsh, Top. Stereochem. 1, 199 (1967)
E. W. Delia, J. Am. Chem. Soc. 89, 5221 (1967).
R. Gallo, Prog. Phys Org. Chem. 14, 115 (1983).
W. H. Dawson, D. H. Hunter, and C. J. Willis, J. Chem. Soc, Chem. Commun. 874 (1980).
R. E. Fernandez, Diss. Abstr. Int. B48, 3569 (1988).
S. Hellmann, H.-D. Beckhaus, and C. Rüchardt, Chem. Ber 116, 2238 (1983).
K. V. Scherer, Jr., T. Ono, K. Yamanouchi, R. Fernandez, P. Henderson, and H. Goldwhite, J. Am. Chem. Soc. 107, 718 (1985)
C. Tonelli and V. Tortelli, J. Chem. Soc, Perkin Trans. 1, 23 (1990).
K. V. Scherer, Jr., in: Fluorine: The First Hundred Years (R. E. Banks, D. W. A. Sharp, and J. C. Tatlow, eds.), Appendix 11.5, Elsevier, New York (1986).
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Smart, B.E. (1994). Characteristics of C-F Systems. In: Banks, R.E., Smart, B.E., Tatlow, J.C. (eds) Organofluorine Chemistry. Topics in Applied Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1202-2_3
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