Highly electophilic, gem- and spiro- activated trichloromethylnitrocyclopropanes: synthesis and structure
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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 NO 2 and CCl 3 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.