天然物のNMRスペクトルに関する研究 (第5報) : 13種のランタノイドシフト試薬の評価について

概要

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Thirteen lanthanoide shift reagents [Ln (DPM) 3, Ln (FOD) 3, Ln (PTA) 3, Ln (TBC) 3 and Ln (TFC) 3; Ln=Eu, Yb, Pr, Ho or Dy] in 1H-NMR spectroscopy were evaluated with regard to solubility, interference of the t-butyl signal of the ligands, line broadening effects, and shift strength relative to Eu (DPM) 3 reagent, using cholestanol and its oxo, acetoxy, and methyl ether derivatives as substrates. From the data obtained, it was concluded that Eu (FOD) 3 as well as Eu (DPM) 3 and Pr (FOD) 3 are the most satisfactory shift reagents, giving sizeable downfield and upfield shifts, respectively. Yb (FOD) 3 and Ho (FOD) 3 were also superior downfield and upfield shift reagents, respectively, in co-ordinating more effectively with weak Lewis bases such as ether, though the line broadening effect was somewhat serious. The complexing ability of the substrates with the shift reagents decreased in the order : alcohol >ketone>ester>ether.
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