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- W4210294527 abstract "[53101-93-2] C4H3LiO (MW 74.007) InChI = 1S/C4H3O.Li/c1-2-4-5-3-1;/h1,3-4H; InChIKey = YZRGAYABLKGRFQ-UHFFFAOYSA-N (nucleophilic organolithium reagent useful for alkylation; addition to ketones, acid chlorides, aldehydes, amides, lactones, carbon dioxide, nitrones, epoxides, sulfinate esters, boronic esters, metal carbonyls, borates, metal halides; affords intermediates for organometallic coupling reactions) Alternate Name: β-furyllithium. Preparative Methods: metalation of Furan at the 3-position requires a metal–halogen1-7 or metal–metal exchange8 since deprotonation of furan occurs preferentially at the 2-position. 3-Lithiofuran 1 (eq 1)1-3 is prepared by the treatment of 3-iodofuran (2a) with n‐Butyllithium in ether or THF (−78 °C);4, 5 by the treatment of 3-bromofuran (2b) with n-butyllithium in THF (−78 °C);6, 7 or by the reaction of 3-tri-n-butylstannylfuran (2c) with n-butyllithium in THF (−78 °C).8 (1) Handling, Storage, and Precautions: the reagent is generated in situ, under anhydrous conditions in an inert atmosphere at low temperatures (≤−40 °C), and used shortly after preparation. The ability to store the reagent is not clear. As n-BuLi is employed, the precautions for preparation and use would mirror those of n-BuLi and related organometallic reagents. It has been demonstrated that good temperature control is important to the regiochemical integrity of the reagent. Temperatures exceeding −40 °C during the course of reagent generation and use permit isomerization of 3-lithiofuran to the more thermodynamically stable 2-lithiofuran (eq 2).7 (2)" @default.
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- W4210294527 date "2007-09-17" @default.
- W4210294527 modified "2023-10-14" @default.
- W4210294527 title "3-Lithiofuran" @default.
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- W4210294527 doi "https://doi.org/10.1002/047084289x.rl020m.pub2" @default.
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