772-46-3Relevant articles and documents
2,2,5,5-Tetramethyltetrahydrofuran (TMTHF): A non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents
Byrne, Fergal,Forier, Bart,Bossaert, Greet,Hoebers, Charly,Farmer, Thomas J.,Clark, James H.,Hunt, Andrew J.
, p. 3671 - 3678 (2017/08/15)
An inherently non-peroxide forming ether solvent, 2,2,5,5-tetramethyltetrahydrofuran (2,2,5,5-tetramethyloxolane), has been synthesized from readily available and potentially renewable feedstocks, and its solvation properties have been tested. Unlike traditional ethers, its absence of a proton at the alpha-position to the oxygen of the ether eliminates the potential to form hazardous peroxides. Additionally, this unusual structure leads to lower basicity compared with many traditional ethers, due to the concealment of the ethereal oxygen by four bulky methyl groups at the alpha-position. As such, this molecule exhibits similar solvent properties to common hydrocarbon solvents, particularly toluene. Its solvent properties have been proved by testing its performance in Fischer esterification, amidation and Grignard reactions. TMTHF's differences from traditional ethers is further demonstrated by its ability to produce high molecular weight radical-initiated polymers for use as pressure-sensitive adhesives.
Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst
Li, Gang,Leow, Dasheng,Wan, Li,Yu, Jin-Quan
supporting information, p. 1245 - 1247 (2013/03/13)
Weak coordination is powerful! A PdII-catalyzed olefination of ortho-C-H bonds of arenes directed by weakly coordinating ethers is developed by using monoprotected amino acid (MPAA) ligands. This finding provides a method for chemically modifying ethers, which are abundant in natural products and drug molecules. HFIP=hexafluoroisopropanol. Copyright
Iron(II) chloride-mediated addition of dialkylmagnesium to carbonyl compounds
Sada, Mutsumi,Matsubara, Seijiro
, p. 800 - 801 (2008/12/21)
Addition reactions to carbonyl compounds with a complex reagent, prepared from organomagnesium and iron(II) chloride, were examined. The reagent works as effective nucleophile to an easily enolizable ketone such as β-tetralone; it also added to keto ester chemoselectively. Copyright
