Highly electrophilic, <i>gem-</i> and <i>spiro-</i> activated trichloromethylnitrocyclopropanes: synthesis and structure
New highly electrophilic <i>gem</i>- and <i>spiro</i>-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 <i>trans</i>-configuration of -NO<sub>2</sub> and -CCl<sub>3</sub> 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.
Authors
- Aleksander V. Vasilyev (ORCID: https://orcid.org/0000-0003-3628-1492)
- Igor A. Litvinov (ORCID: https://orcid.org/0000-0003-4991-1908)
- O. Yu. Ozerova (ORCID: https://orcid.org/0009-0001-6197-2888)
- S. V. Makarenko (ORCID: https://orcid.org/0000-0002-7284-5147)
- Mikhail V Grigoriev
- Ilia A Pilipenko
- Darya V Spiridonova
Institutions
- St Petersburg University (RU)
- Herzen University (RU)
- Saint Petersburg State Forest Technical University (RU)
- A.E. Arbuzov Institute of Organic and Physical Chemistry (RU)
Publication Details
- Journal
- Beilstein Journal of Organic Chemistry
- Published
- 2026-01-14
- DOI
- https://doi.org/10.3762/bjoc.22.5
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00