Abstract:
Cyclopropanation of 1-methylidene-2-phenylcyclopropane with dimethyl diazomalonate affords new dimethyl 4-phenyl-spiro[2.2]pentane-1,1-dicarboxylate. On contact with EtAlCl2, this compound undergoes opening of both cyclopropane rings to give dimethyl (2-chloromethyl-3-phenylallyl)malonate. Its EtAlCl2-assisted reaction with methyl 5′-methylspiro[cyclo-propane-1,3′-pyrazoline]-5′-carboxylate proceeds as the 1,3:1′,5′-addition to afford mainly 3-(2-chloroethyl)-1-cyclo-propylmethyl-1H-pyrazoline derivative.
Citation:
D. A. Denisov, D. D. Borisov, K. V. Potapov, R. A. Novikov, Yu. V. Tomilov, “4-Phenylspiro[2.2]pentane-1,1-dicarboxylate: synthesis and reactions with EtAlCl2 and 4,5-diazaspiro[2.4]hept-4-ene derivative”, Mendeleev Commun., 29:4 (2019), 417–418
Linking options:
https://www.mathnet.ru/eng/mendc1543
https://www.mathnet.ru/eng/mendc/v29/i4/p417
This publication is cited in the following 4 articles:
Denis D. Borisov, Roman A. Novikov, Yury V. Tomilov, “Three-Component Synthesis of Substituted Perhydropyrans from β-Styrylmalonates, Aldehydes, and Alkoxyaluminum Dichlorides”, Org. Lett., 26:5 (2024), 1022
Anastasia A. Levina, Roman A. Novikov, Denis D. Borisov, Maxim A. Novikov, Yury V. Tomilov, “Development of cationic gallium phthalocyanine catalysts for the chemistry of donor-acceptor cyclopropanes and its reactions with aldehydes”, Molecular Catalysis, 550 (2023), 113480
D. A. Denisov, R. A. Novikov, Yu. V. Tomilov, “Donor-acceptor bicyclopropyl configuration-fixed by an additional trimethylene bridge: synthesis and Lewis acid-catalyzed tandem three-membered rings opening”, Russ Chem Bull, 70:8 (2021), 1568
Konstantin V. Potapov, Dmitry A. Denisov, Valeriia V. Glushkova, Roman A. Novikov, Yury V. Tomilov, “Donor–Acceptor Bicyclopropyls as 1,6-Zwitterionic Intermediates: Synthesis and Reactions with 4-Phenyl-1,2,4-triazoline-3,5-dione and Terminal Acetylenes”, J. Org. Chem., 85:23 (2020), 15562
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