Journal of the Chemical Society. Perkin transactions I p. 1125 - 1131 (1981)
Update date:2022-07-29
Topics:
Knight, David W.
Nott, Andrew P.
Methods for the generation of the dianionic species lithium 5-lithiofuran-2-carboxylate (5) and lithium 2-lithiofuran-3-carboxylate (21) from furan-2- and furan-3-carboxylic acids recpectively are described.The reactions of (5) and (21) with a range of electrophiles have been examined; in general these are very efficient with aldehydes and ketones but not as satisfactory with alkyl halides and epoxides.The dianions do not couple with allylic or benzylic halides, nor with nitriles or orthoesters.The generation of lithium-5-lithio-3-methylfuran-2-carboxylate (15) from 3-methyl furan-2-carboxylic acid is also described; the chemistry of (15) is very similar to (5) derived from furan-2-carboxylic acid.
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Doi:10.1007/BF00950297
(1981)Doi:10.1039/c39810000655
(1981)Doi:10.1021/ja201138v
(2011)Doi:10.1016/S0040-4020(01)89299-1
(1994)Doi:10.1016/j.bmc.2014.02.041
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