Dipole-stabilized carbanions from thioesters. Evidence for stabilization by the carbonyl group

DB Reitz, P Beak, RF Farney…

文献索引：Reitz,D.B. et al. Journal of the American Chemical Society, 1978 , vol. 100, p. 5428 - 5436

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被引用次数: 20

摘要

Abstract: Reactions are reported which establish that metalation can occur a to the sulfur of methyl and ethyl thioesters to give synthetically useful species. The methyl thiobenzoates 4a, 4b, 4c, and methyl thiopivalate (4d) react with lithium 2, 2, 6, 6-tetramethylpiperidide (LiTMP) in tetrahydrofuran at ambient temperature to give the corresponding dibenzoylmethanes, 5a, 5b, Sc, and dipivaloylmethane (5d), respectively, in yields of 60- ...