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(g) Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173.
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(i) Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832.
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(j) Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565.
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(b) Massa, M. A.; Patt, W. C.; Ahn, K.; Sisneros, A. M.; Herman, S. B.; Doherty, A. Bioorg. Med. Chem. Lett. 1998, 8, 2117.
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18
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1842552632
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note
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For leading references on the mechanism of this reaction, see ref 4 and references therein.
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19
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85082508646
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For examples of halogen dance reactions that are driven by differential acidities on thiophenes, see ref 11a and the following: Sauter, F.; Fröhlich, H.; Kalt, W. Synthesis 1989, 771.
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Sauter, F.1
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20
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0000889418
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For a review of the chemistry of lithio thiazole, see: Iddon, B. Heterocycles 1995, 41, 533.
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Iddon, B.1
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21
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0000107780
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For other examples where an in situ trapping with a silyl chloride proceeds faster than a halogen dance, see: (a) Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. Heterocycles 1983, 20, 2035.
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Heterocycles
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Kano, S.1
Yuasa, Y.2
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Shibuya, S.4
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22
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(b) Bury, P.; Hareau, G.; Kocienski, P.; Dhanak, D. Tetrahedron 1994, 50, 8793.
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Dhanak, D.4
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23
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0028965423
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(c) Cochennec, C.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Synthesis 1995, 321.
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Cochennec, C.1
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24
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(d) Arzel, E.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Heterocycles 1999, 50, 215.
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25
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0032447309
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For a review of nucleophilic reactions of 2-lithiothiazole, see: Dondoni, A. Synthesis 1998, 1681.
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Dondoni, A.1
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26
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0025143597
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Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509.
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27
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0001059518
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For a related transformation, see: Burke, S. D.; Deaton, D. N.; Olsen, R. J.; Armistead, D. M.; Blough, B. E. Tetrahedron Lett. 1987, 28, 3905.
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Blough, B.E.5
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28
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1842604836
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note
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This reaction requires prior purification of the anhydride by recrystallization from ethyl acetate in order to minimize the formation of several byproducts.
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