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Beilstein Arch. 2025, 202559. https://doi.org/10.3762/bxiv.2025.59.v1
Published 17 Oct 2025
New highly electrophilic gem- and spiroactivated trichloromethylnitrocyclopropanes were obtained by the Michael Initiated Ring Closure (MIRC) reaction of 1-bromo-1-nitro-3,3,3-trichloropropene with linear and cyclic CH-acids catalyzed by bases. Conditions for obtaining the target cyclopropanes were optimized. The process is characterized by high diastereoselectivity and allows obtaining cyclopropanes with the trans-configuration of NO2 and CCl3 groups. Monocyclic (based on malonic acid dinitrile, methyl cyanoacetate, ethyl cyanoacetate, benzoylacetonitrile), spirocarbo- (based on 1,3-indanedione) and spiroheterocyclic (based on Meldrum's acid, 3-methyl-1-phenyl-5-pyrazolone, dimethylbarbituric acid) cyclopropane structures were isolated and characterized.
Keywords: Cyclopropanes; nitrocyclopropanes; bromonitropropene; trichloromethyl group; CH-acids; X-ray
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Pilipenko, I. A.; Grigoriev, M. V.; Ozerova, O. Y.; Litvinov, I. A.; Spiridonova, D. V.; Vasilyev, A. V.; Makarenko, S. V. Beilstein Arch. 2025, 202559. doi:10.3762/bxiv.2025.59.v1
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