RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2004(16): 2620-2624
DOI: 10.1055/s-2004-831209
DOI: 10.1055/s-2004-831209
PAPER
© Georg Thieme Verlag Stuttgart · New York
Indium(III) Halide Mediated S N 2′ Reactions of Substituted Allenols: Synthesis of 2-Halo-1,3-dienes
Weitere Informationen
Received
13 April 2004
Publikationsdatum:
02. September 2004 (online)
Publikationsverlauf
Publikationsdatum:
02. September 2004 (online)
Abstract
Treatment of various substituted allenols with indium(III) halide in benzene gave (Z)- or (E)-2-halo-1,3-dienes in moderate to good yields. In most cases, (2Z)-halo-1,3-dienes were obtained as major products.
Key words
allenol - indium(III) halide - 2-halo-1,3-diene - SN2′ reaction
-
1a A recent review:
Pae AN.Cho YS. Curr. Org. Chem. 2002, 6: 715 -
1b
Zhang J.Li C.-J. J. Org. Chem. 2002, 67: 3969 -
1c
Cho YS.Kim HY.Cha JH.Pae AN.Koh HY.Choi JH.Chang MH. Org. Lett. 2002, 4: 2025 -
1d
Ranu BC.Hajra A. J. Chem. Soc., Perkin Trans. 1 2001, 2262 -
1e
Marshall JA.Hinkle KW. J. Org. Chem. 1996, 61: 105 -
1f
Li X.Loh T.-P. Tetrahedron: Asymmetry 1996, 7: 1535 -
1g
Kobayashi S.Busujima T.Nagayama S. Angew. Chem., Int. Ed. Engl. 1997, 36: 980 - 2
Fringuelli F.Taticchi A. Dienes in the Diels-Alder Reaction John Wiley & Sons, Inc.; New York: 1990. -
3a
Roush WR.Moriarty KJ.Brown BB. Tetrahedron Lett. 1990, 31: 6509 -
3b
Ogasawara M.Ikeda H.Hayashi T. Angew. Chem. Int. Ed. 2000, 39: 1042 -
3c
Pornet J.Randrianoelina B. Tetrahedron Lett. 1981, 22: 1327 - 4
Horváth A.Bäckvall J.-E. J. Org. Chem. 2001, 66: 8120 - 5
Ma S.Wang G. Tetrahedron Lett. 2002, 43: 5723 -
6a
Issac MB.Chan TH. J. Chem. Soc., Chem. Commun. 1995, 1003 -
6b
Cho YS.Lee JE.Pae AN.Choi KI.Koh HY. Tetrahedron Lett. 1999, 40: 1725 -
6c
Yi X.-H.Meng Y.Li C.-J. J. Org. Chem. 1998, 63: 7472 - 7
Kang H.-Y.Kim Y.-T.Yu Y.-K.Cha JH.Cho YS.Koh HY. Synlett 2004, 45