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

Lookup NU author(s): Dr Matt HopkinsonORCiD

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Abstract

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.

Publication metadata

Author(s): Maas LM, Schmid JR, Fasting C, Vossnacker P, Mavroskoufis A, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2021

Volume: 101

Print publication date: 19/11/2021

Online publication date: 22/10/2021

Acceptance date: 19/10/2021

Date deposited: 22/11/2021

ISSN (print): 0040-4020

Publisher: Elsevier

URL: https://doi.org/10.1016/j.tet.2021.132512

DOI: 10.1016/j.tet.2021.132512

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