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Review | Special issue | Vol 67, No. 1, 2006, pp.443-460
Published online, 8th September, 2005
DOI: 10.3987/REV-05-SR(T)1
Criss-cross Cycloaddition Reactions with Hexafluoroacetone Azine. Mechanism and Some Synthetic Applications

Klaus Burger,* Lothar Hennig, Olaf Zeika, and Andrea Lux

*Department of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany

Abstract

Using hexafluoroacetone azine as model compound we have shown that azomethine imines are the [1.1]intermediates of the criss-cross cycloaddition. The readily available trifluoromethyl substituted azomethine imines are reactive species exhibiting considerable synthetic potential for the construction of partially fluorinated heterocycles and polymers.