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Keywords = tantalum (V) trichloride

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12 pages, 2027 KiB  
Article
The TaCl5-Mediated Reaction of Dimethyl 2-Phenylcyclopropane-1,1-dicarboxylate with Aromatic Aldehydes as a Route to Substituted Tetrahydronaphthalenes
by Tat’yana P. Zosim, Rita N. Kadikova, Roman A. Novikov, Alexander A. Korlyukov, Oleg S. Mozgovoj and Ilfir R. Ramazanov
Molecules 2024, 29(12), 2715; https://doi.org/10.3390/molecules29122715 - 7 Jun 2024
Cited by 2 | Viewed by 1222
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Section Organic Chemistry)
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