Reductive Dimerization of Alkylidenemalonates Using Samarium(II) Diiodide and 1H-NMR Behavior of the Dimers, 2, 3-Diaryl-1, 1, 4, 4-butanetetracarboxylates

Masayuki YAMASHITA; Kazunori OKUYAMA; Ikuo KAWASAKI; Seikou NAKAMURA; Rumiko NAGAMINE; Takako TSUJITA; Shunsaku OHTA

doi:10.1248/cpb.48.1799

Reductive Dimerization of Alkylidenemalonates Using Samarium(II) Diiodide and ¹H-NMR Behavior of the Dimers, 2, 3-Diaryl-1, 1, 4, 4-butanetetracarboxylates

Masayuki YAMASHITA, Kazunori OKUYAMA, Ikuo KAWASAKI, Seikou NAKAMURA, Rumiko NAGAMINE, Takako TSUJITA, Shunsaku OHTA

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Keywords: samarium diiodide, alkylidenemalonate, reductive dimerization, 1, 1, 4, 4-butanetetracarboxylate, X-ray crystallographic analysis, MOPAC calculation

JOURNAL FREE ACCESS

2000 Volume 48 Issue 11 Pages 1799-1802

DOI https://doi.org/10.1248/cpb.48.1799

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Abstract

Alkylidenemalonates were readily dimerized in the presence of SmI₂ to give 2, 3-disubsituted 1, 1, 4, 4-butanetetracarboxylates as mixtures of meso and racemic isomers in moderate to good yields. The structure of the less polar isomer of tetraethyl 2, 3-diphenyl-1, 1, 4, 4-butanetetracarboxylate was determined by X-ray crystallographic analysis to be the meso form. Characteristic ¹H-NMR behavior of the meso and racemic isomers is also discussed.

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