1916
E. M. Keramane et al. / Tetrahedron 57 (2001) 1909±1916
London, 1987; Vol. 3, pp. 292. (b) Manhart, M. D. Rev. Infect.
BiBr3 behaves only as an ef®cient catalyst for both the
etheri®cation and the elimination reactions.
BiI3 is totally inactive towards alcohols.
Dis. 1990, 12, 311. (c) Kozak, R. W.; Waldmann, T. A.;
Atcher, R. W.; Gansow, O. A. Trends Biotechnol. 1985, 4,
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Â
4. Boyer, B.; Keramane, E. M.; Montero, J. L.; Roque, J. P.
Synth. Commun. 1998, 28, 1737.
5. Boyer, B.; Keramane, E. M.; Arpin, S.; Montero, J. L.; Roque,
Furthermore the difference in the halogenation ability
between BiCl3 and BiBr3 or BiI3 is in agreement with
HSAB principle.
Â
J. P. Tetrahedron 1999, 55, 1971.
6. Boyer, B.; Keramane, E. M.; Roque, J. P.; Pavia, A. A.
Tetrahedron Lett. 2000, 41, 2891.
Further studies on the application of Bi(III) derivatives to
others reactions are in progress.
Á
7. Labrouillere, M.; Le Roux, C.; Oussard, A.; Gaspard-
Iloughmane, H.; Dubac, J. Bull. Soc. Chim. Fr. 1995, 132, 522.
8. (a) Hudson, H. R.; Kinghorn, R. R. F.; Murphy, W. S. J. Chem.
Soc. 1971, 3593. (b) Gerrard, W.; Hudson, H. R.; Murphy,
W. S. J. Chem. Soc. 1964, 2314. (c) Gerrard, W.; Lappert,
M. F. J. Chem. Soc. 1951, 1020. (d) Gerrard, W.; Lappert,
M. F. J. Chem. Soc. 1955, 3084.
4. Experimental
1H NMR was recorded in a BRUCKER ACE-250 instru-
ment at 250 MHz in CDCL3 solutions. GC analysis was
performed with a DELSI 330 apparatus. Optical rotations
were measured using a PERKIN ELMER 241 polarimeter
with speci®c rotations determined at 208C. All starting
materials, alcohols, optically active alcohols, BiCl3, BiBr3,
BiI3, BiOCl, were commercially available (Aldrich).
9. (a) Lange, K. C. H; Klapotke, T. M. In The Chemistry of
È
Arsenic, Antimony and Bismuth Compounds; Pataõ, S., Ed.;
Wiley: New York, 1994; pp 315. (b) Majafuji, T.; Mutoh,
T.; Satoh, K.; Tsunenari, K. Organometallics 1995, 14,
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Errington, R. J.; Havelock, J.; Lightfoot, P.; Norman, N. C.;
Scott, A. J. Inorg. Chem. 1996, 35, 3709. (d) Di Vaira, M.;
Mani, F.; Stoppioni, P. Eur. J. Inorg. Chem. 1999, 833.
(e) Kallal, K.; Coin, C.; Dunach, E.; Postel, M. New J.
Chem. 1997, 21, 495 (and references cited therein).
(f) Genge, A. R. J.; Levason, W.; Reid, G. Chem. Commun.
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Whatever the bismuth derivative (BiCl3, BiBr3, BiI3,
BiOCl), halogenation reactions were performed following
the general procedure previously described.4 The same
method was used for the reaction achieved in the presence
of the 2,3-dimethylbut-2-ene.
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