Abstract
A new method for cyclopropanation of olefins with the BuLi—AlCl3—CH2I2 reagent system was developed. The reaction is tolerant of a wide range of unsaturated alkyl- and aryl-substituted hydrocarbons of linear and cyclic structure (octene-1, decene-1, tetradecene-1, styrene, 1-vinylnaphthalene, cyclohexene, cyclooctene, myrcene) and gives high yields (63–87%) of the corresponding cyclopropanation products. The reactions involving the sterically hindered olefins (2-cyclobutylideneadamantane, 2,2′-bi(adamantylidene)) produce cyclopropane-containing polycyclic hydrocarbons in 40–45% yields.
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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 165–168, January, 2022.
This work was financially supported by the Russian Foundation for Basic Research (Project No. 19-33-60046). Adamantane-substituted substrates were synthesized in the framework of the State Task of the Ministry of Science and High Education of the Russian Federation (No. AAAAA19-119022290009-3/FMRS-2022-0076). Allyl amines and enamines were synthesized in the framework of the State Task of the Ministry of Science and High Education of the Russian Federation (No. AAAAA19-119022290008-6/FMRS-2022-0075). Structures of the synthesized compounds were evaluated using the equipment of the Regional Center for Collective Use of Unique Equipment “Agidel” at the Institute of Petrochemistry and Catalysis, UFRC RAS.
No human or animal subjects were used in this research.
The authors declare no competing interests.
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Zosim, T.P., Sadykova, F.T., Ramazanov, I.R. et al. BuLi—AlCl3—CH2I2 as a new reagent system for olefin cyclopropanation. Russ Chem Bull 71, 165–168 (2022). https://doi.org/10.1007/s11172-022-3391-8
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DOI: https://doi.org/10.1007/s11172-022-3391-8