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Synthesis 2008(18): 2899-2904  
DOI: 10.1055/s-2008-1067221
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Application of 1-(3-Bromo-3,3-difluoroprop-1-ynyl)benzenes in Diels-Alder Reactions: Synthesis of ortho-CF2Br-Substituted Biaryls

Vasiliy M. Muzalevskiya, Valentine G. Nenajdenko*a, Aleksey V. Shastinb, Elizabeth S. Balenkovaa, Günter Haufe*c
a Department of Chemistry, Moscow State University, Leninskie Gory, Moscow 119992, Russian Federation
e-Mail: nen@acylium.chem.msu.ru;
b Institute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russian Federation
e-Mail: shastin@icp.ac.ru;
c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Correnstr. 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
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Publikationsverlauf

Received 26 March 2008
Publikationsdatum:
06. August 2008 (online)

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Abstract

1-(3-Bromo-3,3-difluoroprop-1-ynyl)benzenes were found to be good dienophiles in Diels-Alder reactions. Based on this key reaction a new pathway towards biaryls with an ortho-CF2Br group was elaborated.

Key words

alkynes - biaryls - bicyclic compounds - Diels-Alder reaction­ - fluorine

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