This article is cited in 4 papers

Communications

4-Phenylspiro[2.2]pentane-1,1-dicarboxylate: synthesis and reactions with EtAlCl₂ and 4,5-diazaspiro[2.4]hept-4-ene derivative

D. A. Denisov, D. D. Borisov, K. V. Potapov, R. A. Novikov, Yu. V. Tomilov

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

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.

Language: English

DOI: 10.1016/j.mencom.2019.07.020

Bibliographic databases:

•