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• W1983508968 abstract "Abstract In the presence of inorganic iodide, the methoxy CO bond in 2‐methoxyfurans may be cleaved to afford the corresponding lactonic anion. Due to the presence of an electron‐withdrawing group at the 3‐position, the alkylation with normal organic iodides occurred at the 3‐position highly regioselectively. However, when electron‐deficient allylic iodides with an electron‐withdrawing group at the 2‐position were used the 5‐alkylation products were formed as the major products with sodium iodide as the catalyst. With magnesium iodide as the catalyst, the 5‐allylation occurred highly regioselectively. As a whole, the 3‐ vs. 5‐alkylation selectivity may be determined by the relative steric hindrance at the 3‐ and 5‐positions and the electronic effect of the allylic iodides. A rationale was proposed." @default.
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• W1983508968 date "2012-04-13" @default.
• W1983508968 modified "2023-10-18" @default.
• W1983508968 title "Tuning of Regioselectivity in Inorganic Iodide-Catalyzed Alkylation of 2-Methoxyfurans via Electronic and Steric Effects" @default.
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• W1983508968 doi "https://doi.org/10.1002/adsc.201100337" @default.
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