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Halogen and Pseudo-Halogen Dance Reactions and Synthetic Scope of Accessible Targets: Novel Examples on Thiophenes, Furans and (Spacer-Extended) Biaryls

J. Fröhlich, C. Hametner, and W. Skranc

Institute of Organic Chemistry, Vienna University of Technology
A-1060 Vienna, Austria


Halogen Dance techniques as well as their selective preventions developed for the first time within our research group have been proven to be useful and versatile synthetic methods to access a whole host of novel multi-substituted thiophenes and furans [1], [2]. Some examples thereof have already been displayed during ECHET96 by our group [3], [4], [5]. Extension to bromo-bithiophenes allowed selective mono and double halogen migration. Moreover, butyl lithium induced ring opening reactions on specifically designed model substrates led to novel conjugated en-ynes. Within this lecture transfer of this methodology to hetero biaryls extended through aryl, hetaryl and alkynyl spacers will be presented.
Spacer-extended Bithienyl Ring-opened Product