Abstract
A reaction of octa-1,7and deca-1,9-dienes with an excess of bromofluorocarbene proceeds predominantly with the formation of a monoadduct, whereas the bis-adduct can be prepared by repeated cyclopropanation. The [1+2] cycloaddition of dichlorocarbene to the monoadduct of bromofluorocarbene with deca-1,9-diene gave a new bis(cyclopropane) containing gem-dichloro- and gem-bromofluorocyclopropane fragments in one molecule. The bis-adducts obtained were subjected to the heterocyclization with nitronium triflate: in the case of bis(gem-bromofluorocyclopropane) the reaction proceeded with retention of one dihalocyclopropane fragment and gave mononuclear pyrimidine N-oxide.
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Based on the materials of the International Congress on the Heterocyclic Chemistry “KOST-2015” (October 18–23, 2015, Moscow, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1750–1756, July, 2016.
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Sedenkov, K.N., Averin, E.B., Grishin, Y.K. et al. Bis(gem-dihalocyclopropanes): synthesis and heterocyclization upon treatment with nitronium triflate. Russ Chem Bull 65, 1750–1756 (2016). https://doi.org/10.1007/s11172-016-1506-9
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DOI: https://doi.org/10.1007/s11172-016-1506-9