Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties

• Autorzy: Janus E. , Gano M.

Identyfikatory

DOI

10.1515/pjct-2017-0054

• Języki publikacji: EN

Abstrakty

EN

Six new chiral pyrolidinium salts with chiral substituent at quaternary nitrogen atom were synthesized with high overall yields from (-)-menthol as cheap chiral precursor and were identified by NMR and HRMS spectroscopy. It was shown that anion type had the effect on chemical shift of protons adjacent to quaternary nitrogen atom and physical properties of these salts. Salts with NTf₂  or NPf₂  were in a liquid state at room temperature and characterized with the highest thermal stability among others. Furthermore, chiral ionic liquid with NTf₂  anion was used as solvent in Diels-Alder reaction and gave higher yield and stereoselectivity than in ionic liquids with achiral cations. Synthesized chiral salts have the potential as chiral solvents in synthesis and auxiliaries in analytical methods to improve chiral recognition.

Słowa kluczowe

EN

pyrrolidinium chiral salts; chiral ionic liquids; menthol; Diels-Alder reaction

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2017
• Tom: Vol. 19, nr 3
• Strony: 92--98
• Opis fizyczny: Bibliogr. 34 poz., rys., tab.

Twórcy

autor

Janus E.

• West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Department of Organic Chemical Technology, Pułaskiego 10, 70-322 Szczecin, Poland

autor

Gano M.

• West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Department of Organic Chemical Technology, Pułaskiego 10, 70-322 Szczecin, Poland

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Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).