title: Symmetrical imidazolium chloride based on (-)-menthol: synthesis, characterization, and theoretical model of the reaction.
abstract: New symmetrical imidazolium chloride from a natural chiral pool of (1R,2S,5R)-(-)-menthol can be efficiently prepared by two different methods. The first method involves a specific type of Menschutkin reaction using novel 1-(1R,2S,5R)-(-)-menthoxymethylimidazole as amine, chloromethyl (1R,2S,5R)-(-)-menthyl ether as quaternization agent, and hexane as solvent. In the second method, imidazole, chloromethyl (1R,2S,5R)-(-)-menthyl ether, and DMF are used. To understand this specific type of the reaction, quantum chemical calculations at the DFT level have been used. The preparation and characterization of 1,3-bis[(1R,2S,5R)-(-)-menthoxymethyl]imidazolium chloride are reported.
authors.affiliation: †Wrocław University of Technology, Faculty of Chemistry, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Feder-Kubis
authors.affiliation: †Wrocław University of Technology, Faculty of Chemistry, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Borys
authors.initials: B
authors.lastname: Szefczyk
authors.affiliation: ‡Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznań, Poland.
authors.forename: Maciej
authors.initials: M
authors.lastname: Kubicki