The TaCl<sub>5</sub>-Mediated Reaction of Dimethyl 2-Phenylcyclopropane-1,1-dicarboxylate with Aromatic Aldehydes as a Route to Substituted Tetrahydronaphthalenes
Tat’yana P. Zosim,
Rita N. Kadikova,
Roman A. Novikov,
Alexander A. Korlyukov,
Oleg S. Mozgovoj,
Ilfir R. Ramazanov
Affiliations
Tat’yana P. Zosim
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, Prospekt Oktyabrya 141, 450075 Ufa, Russia
Rita N. Kadikova
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, Prospekt Oktyabrya 141, 450075 Ufa, Russia
Roman A. Novikov
N.D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russia
Alexander A. Korlyukov
A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St., 28 bld. 1, 119334 Moscow, Russia
Oleg S. Mozgovoj
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, Prospekt Oktyabrya 141, 450075 Ufa, Russia
Ilfir R. Ramazanov
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, Prospekt Oktyabrya 141, 450075 Ufa, Russia
It is found that the reaction of dimethyl 2-phenylcyclopropane-1,1-dicarboxylate with 2 equivalents each of aromatic aldehydes and TaCl5 in 1,2-dichloroethane at 23 °C for 24 h after hydrolysis gives substituted 4-phenyl-3,4-dihydronaphtalene-2,2(1H)-dicarboxylates in good yield. This represents a new type of reactions between 2-arylcyclopropane-1,1-dicarboxylates and aromatic aldehydes, yielding chlorinated tetrahydronaphthalenes with a cis arrangement of the aryl and chlorine substituents in the cyclohexene moiety. A plausible reaction mechanism is proposed.
