Ring opening of epoxides with alcohols using Fe(Cp)2BF4 as catalyst

Sweet polymers: Synthesis and characterization of xylitol-based epoxidized linseed oil resins

“…The hydroxyls of carbohydrates have an increased reactivity compared with other simple alcohols, and we expect that ZnCl 2 may be the correct catalyst for opening epoxy rings with the primary hydroxyl from a polyol molecule without side reactions. Other catalysts, such as Fe(Cp) 2 BF 4 [38] and graphite oxide [39] that have shown a good performance in the opening of epoxy rings with alcohols in small molecules, may also be used with for same purpose by adjusting and optimizing the reaction conditions to obtain the desired product.…”

Well-defined epoxide-containing styrenic polymers and their functionalization with alcohols

“…Heterogeneous acidic catalysts that have been successfully employed for this purpose include sulfonated polymers (Amberlyst‐15 and Nafion‐H), neutral alumina, mesoporous aluminosilicate, organotin phosphate condensates (OPCs), and Fe 3+ ‐montmorillonite, but it is unlikely that they could achieve sufficient interaction with the pendant functionalities of polymers to efficiently promote functionalization. Soluble compounds or complexes of main group metals, transition metals, and lanthanides are well‐known for their Lewis acidity and have been investigated specifically for their ability to catalyze the alcoholysis of epoxides. The catalytic activities of non‐metallic Lewis acids like BF 3 , CBr 4 , hydrazine sulphate, molecular iodine, iminium triflate, and trimethylsilyl triflate, as well as compounds able to participate in single‐electron reactions like 2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone, tetracyanoethylene, ceric ammonium nitrate, N ‐methylpyrrolidine‐2‐one hydrotribromide, and 1‐benzyl‐2,4,6‐triphenylpyridinium tetrafluoroborate, have also been explored.…”

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“…22 Other Lewis acids, such as iron(III) chloride, indium(III) chloride, or zirconium(IV) chloride, were also able to promote the reaction, but ferrocenium tetrafluoroborate was the most efficient (Scheme 6). …”