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Highly electrophilic, gem- and spiro-activated trichloromethylnitrocyclopropanes: synthesis and structure
Ilia A Pilipenko1,2, Mikhail V Grigoriev1, Olga Yu Ozerova2
1Department of Chemistry, Saint-Petersburg State Forest Technical University, Saint-Petersburg 194021, Russia.
Abstract:
New highly electrophilic gem- and spiro-activated 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 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, dimethylbarbituric acid, 3-methyl-1-phenyl-5-pyrazolone) cyclopropane structures were isolated and characterized.
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