Methyl transfer in quaternary alkylammonium salts, derivatives of 1,4:3,6-dianhydrohexitols

Karol Sikora , Andrzej Nowacki , Beata Liberek , Barbara Dmochowska

Abstract

An unexpected side-reaction took place during the synthesis of quaternary ammonium salts with O-triflyl derivatives of 1,4:3,6-dianhydrohexitols and tertiary alkylamines. The products were identified as tertiary amine derivatives of 1,4:3,6-dianhydrohexitol and tetraalkylammonium triflate. It was found that formation of the products was the consequence of the methyl group migration from QAS formed to the amine present in excess in the reaction mixture. Such reaction is a case of transquaternization, in which the exchange of the methyl group between two amines occurs.
Author Karol Sikora (FCh / DOCh / LG) - [Medical Uniwersity of Gdańsk (GUMed)]
Karol Sikora,,
- Laboratory of Glycochemistry
- Gdański Uniwersytet Medyczny
, Andrzej Nowacki (FCh / DOCh / LG)
Andrzej Nowacki,,
- Laboratory of Glycochemistry
, Beata Liberek (FCh / DOCh / LG)
Beata Liberek,,
- Laboratory of Glycochemistry
, Barbara Dmochowska (FCh / DOCh / LCCh)
Barbara Dmochowska,,
- Laboratory of Carbohydrate Chemistry
Journal seriesJournal of Molecular Structure, ISSN 0022-2860, e-ISSN 1872-8014, (N/A 70 pkt)
Issue year2020
Vol1206
Pages1-7
Publication size in sheets0.5
Article number127701
Keywords in EnglishQuaternary ammonium salts, methyl transfer, 1,4:3,6-dianhydro-D-glucitol, 1,4:3,6-dianhydro-D-mannitol, transquaternization
ASJC Classification1602 Analytical Chemistry; 1604 Inorganic Chemistry; 1605 Organic Chemistry; 1607 Spectroscopy
DOIDOI:10.1016/j.molstruc.2020.127701
URL https://doi.org/10.1016/j.molstruc.2020.127701
Languageen angielski
LicenseOther; published final; Uznanie Autorstwa - Użycie Niekomercyjne - Bez utworów zależnych (CC-BY-NC-ND); with publication
Score (nominal)70
Score sourcejournalList
ScoreMinisterial score = 70.0, 29-01-2020, ArticleFromJournal
Publication indicators Scopus SNIP (Source Normalised Impact per Paper): 2018 = 0.807; WoS Impact Factor: 2018 = 2.12 (2) - 2018=1.861 (5)
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