A theoretical investigation of the reaction mechanism for hydrogenated furan formation under Prins reaction conditions in trifluoroacetic acid medium

Autor:	I. V. Vakulin, Rifkat F. Talipov, R. R. Syrlybaeva
Rok vydání:	2013
Předmět:	chemistry.chemical_compound Reaction mechanism chemistry Ab initio quantum chemistry methods Furan Trifluoroacetic acid Physical and Theoretical Chemistry Prins reaction Photochemistry Catalysis Ion
Zdroj:	Reaction Kinetics, Mechanisms and Catalysis. 109:301-313
ISSN:	1878-5204 1878-5190
DOI:	10.1007/s11144-013-0563-4
Popis:	The formation mechanism of hydrogenated furans by coupling between terminal alkenes and aldehydes in trifluoroacetic acid medium were investigated by ab initio calculations, the main attention was focused on the study of the rate controlling step. Two possible mechanisms for this reaction involving unsaturated alkoxycarbenium ions or dioxolenium ions as a key intermediate were considered. It was shown that the mechanism of formation of 3-alkylsubstituted hydrogenated furans in trifluoroacetic acid under Prins reaction conditions preferably includes recyclization of 3-(2-hydroxyethyl)-1-trifluoromethyl-2,5-dioxolenium ions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::68fabcc067476c7d2be98e788816e52f https://doi.org/10.1007/s11144-013-0563-4 Zobrazit plný text záznamu Full text from SpringerLink