357-39-1Relevant academic research and scientific papers
Hexaalkylguanidinium trifluoromethanesulfonates - A general synthesis from tetraalkylureas and triflic anhydride, and properties as ionic liquids
Kunkel, Helene,Maas, Gerhard
, p. 3746 - 3757 (2008/03/18)
More than thirty hexaalkylguanidinium trifluoromethanesulfonates 12 were prepared from N,N-diethyl-N′,N′-dimethylurea, N,N-dibutyl-N′, N′-diethylurea, or tetrabutylurea, triflic anhydride, and a dialkylamine or cyclic sec-amine in two steps. The combination of the urea and triflic anhydride first yields a bis(tetraalkylamidinio)ether bis(triflate) 10, which is then converted into a salt 12 by reaction with the amine component. The reaction sequence can also be carried out as a one-pot procedure. Eighteen of the prepared guanidinium triflates 12 constitute room-temperature ionic liquids, which were characterized for their melting point, glass transition temperature, viscosity, and refractive index. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Formation of sulfinate esters in the synthesis of triflates
Netscher, Thomas,Bohrer, Patrick
, p. 8359 - 8362 (2007/10/03)
On standard treatment of sterically congested alcohols and phenols with triflic anhydride in the presence of amines, trifluoromethanesulfinyl esters were unexpectedly found. Depending on the reaction conditions and the structures of both hydroxy compound and base, esterified products (yields 5% to 99%) containing 0% to 89% (!) of sulfinates were obtained. The mechanisms of these reactions are discussed. The results of the present study indicate how to avoid unwanted sulfinate formation in triflate synthesis.
