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Activation of Tetrahydrofuran with 2-((Fluoroalkyl)thio)Benzothiazolium Reagents

Activation of Tetrahydrofuran with 2-((Fluoroalkyl)thio)Benzothiazolium Reagents

Activation of Tetrahydrofuran with 2-((Fluoroalkyl)thio)Benzothiazolium Reagents
Image Credit: Elsevier

L. M. Maas, J. R. Schmid, C. Fasting, P. Voßnacker, A. Mavroskoufis, M. N. Hopkinson* – 2021

The ability of BT-SCF3 and related 2-(fluoroalkylthio)benzothiazolium salts to activate tetrahydrofuran (THF) has been investigated. In the presence of carboxylate nucleophiles, ring-opening polymerization reactions affording various fluorinated and non-fluorinated polyethers are observed. Moreover, in the absence of a carboxylate, activation by the benzothiazolium allows for α-deprotonation of THF in the absence of a strong external base. In addition to these experimental studies, the Lewis acidity of BT-reagents is investigated by spectroscopic and quantum chemical methods.

Title
41. Activation of Tetrahydrofuran with 2-((Fluoroalkyl)thio)Benzothiazolium Reagents
Author
L. M. Maas, J. R. Schmid, C. Fasting, P. Voßnacker, A. Mavroskoufis, M. N. Hopkinson*
Publisher
Elsevier
Date
2021
Identifier
DOI: 10.1016/j.tet.2021.132512
Source(s)
Citation
Tetrahedron, 2021, 101, 132512. (Part of the article collection "Fluorine and Chalcogens"; Guest Editors: E. Magnier & G. Dagousset).
Type
Text