The TaCl5-Mediated Reaction of Dimethyl 2-Phenylcyclopropane-1,1-dicarboxylate with Aromatic Aldehydes as a Route to Substituted Tetrahydronaphthalenes

Autor:	Tat’yana P. Zosim, Rita N. Kadikova, Roman A. Novikov, Alexander A. Korlyukov, Oleg S. Mozgovoj, Ilfir R. Ramazanov
Jazyk:	angličtina
Rok vydání:	2024
Předmět:	aromatic aldehydes carbocycles donor–acceptor cyclopropanes tantalum (V) trichloride tetrahydronaphthalenes Organic chemistry QD241-441
Zdroj:	Molecules, Vol 29, Iss 12, p 2715 (2024)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules29122715
Popis:	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.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/823675a5326b4e8d9ee0e08818a05552 Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF Plný text ve formátu HTML
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