有機硫黄化合物の研究(第9報)鎖状α, β-不飽和ケトンにおける回転異性体(s-cis及びs-trans体)の結晶単離とそれらの性質

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The reactions of 1-methyl-4-oxo-cis-and trans-2,6-diphenylthianium tetrafluoroborate with KOH have been carried out. The s-cis (mp 93℃) and s-trans (mp 85℃) conformers of 5-(methylthio)-1,5-diphenyl-(E)-1-penten-3-one of reaction products can be isolated by various solvents and temperature of recrystalization. The various kinds of spectra of s-cis and s-trans forms have been measured in a solution and solid state. The s-cis and s-trans forms exist as an equilibrium mixture of them in the solution and the molen state. On the other hand, the s-cis form is more stable in the solid state and s-trans form gradually rearranges to s-cis form at 80℃. Upon prolonged heating in the presence of water, s-cis and s-trans forms undergo an elimination of methylmercaptane. Moreover, Michael adduct is formerd by heating in alkali solution.
公益社団法人日本薬学会の論文
1985-06-25