Abstract
AbstractNonsymmetrical allenylazines undergo, in boiling xylene, intramolecular cycloaddition by forming an unstable 1,3‐dipole that reacts with an added dipolarophile. In this paper we report the first intra–intermolecular criss‐cross cycloaddition with a fluorinated enone. Although the expected products with three fused heterocycles were not isolated, new bicyclic products were found and characterized. These compounds are formed by a spontaneous transformation involving fluorine atom migration and hydrogen fluoride elimination. A mechanism of the reaction is discussed to explain the formation of these new heterocycles. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
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