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11 For Friedel–Crafts alkylation using alkyl fluorides, see: (a) G. A. Olah,
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Scheme 5 The F–Cl exchange reaction of a,b-d2-b-adamantylethyl
fluorides with Et2AlCl.
Notes and references
1 A recent review for organofluorides, see: T. Hiyama, in Organofluorine
Compounds Chemistry and Applications, Springer, New York, 2000.
2 For recent C–C bond forming reactions using organic fluorides having
an (sp3)C–F bond, see: (a) T. Hatakeyama, S. Ito, M. Nakamura and
E. Nakamura, J. Am. Chem. Soc., 2005, 127, 14192; (b) K. Fuchibe and
T. Akiyama, J. Am. Chem. Soc., 2006, 128, 1434.
3 G. H. Posner, G. M. Gurria and K. A. Babiak, J. Org. Chem., 1977, 42,
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14 D. L. E. Bronnert and B. C. Saunders, Tetrahedron, 1960, 10, 160.
15 J. W. Lown and S. M. S. Chauhan, J. Org. Chem., 1983, 48,
3901.
16 It is known that bond energies of Al–X is 158.5, 102.5, and 88.4 kcal
mol21 for X = F, Br, and I, respectively, see: CRC Handbook of
Chemistry and Physics 1999–2000, ed. D. R. Lide, CRC Press, Boca
Raton, Florida, USA, 81st edn, 2000.
4 (a) K. Toshima, Carbohydr. Res., 2000, 327, 15; (b) P. Tarrant and
R. N. Bull, J. Fluorine Chem., 1988, 40, 201; (c) M. Yoshimatsu,
M. Kawamoto and K. Gotoh, Eur. J. Org. Chem., 2005, 14, 2884.
5 V. A. Petrov, J. Fluorine Chem., 2002, 117, 23.
ˇ
6 B. Koˇsmrlj, B. Kralj and B. Sket, Tetrahedron Lett., 1995, 36, 7921.
7 (a) J. S. Filippo, Jr., A. F. Sowinski and L. J. Romano, J. Org. Chem.,
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Chem., 1981, 46, 3727; (c) M. Namavari, N. Satyamurthy and
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17 It is known that F–Cl substitution of 23 with BCl3 in CH2Cl2 proceeds
via 26, see: ref. 7c.
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