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.
Comparative performance evaluation and systematic screening of solvents in a range of Grignard reactions
Kadam, Asha,Nguyen, Mylinh,Kopach, Michael,Richardson, Paul,Gallou, Fabrice,Wan, Zhao-Kui,Zhang, Wei
, p. 1880 - 1888 (2013/09/24)
The solvent effect on the Grignard reaction of benzyl, aryl and heteroaromatic substrates has been systematically evaluated based on reaction efficiency, ease of subsequent work-up, safety and greenness. 2-Methyltetrahydrofuran (2-MeTHF), which can be derived from renewable resources, had at least an equal if not a superior overall process most notably in suppressing the Wurtz coupling by-product from the benzyl Grignard reactions. It is therefore a recommended alternative solvent to Et2O and THF for the preparation of most Grignard reagents and their subsequent reactions.
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
