The conformational analysis of 1-p-tolyl-2-phenyl-1-propanols, 1-p-tolyl-2-phenylethanol, and 1-p-tolyl-2-phenyl-1-propanone by means of NMR spectroscopy.

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概要

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• The conformations of the diastereomers of 1-<I>p</I>-tolyl-2-phenyl-1-propanols[(<I>RS</I>⁄<I>SR</I>)-<B>3</B> and (<I>RR</I>⁄<I>SS</I>)-<B>3</B>], 1-<I>p</I>-tolyl-2-phenylethanol (<B>4</B>), and 1-<I>p</I>-tolyl-2-phenyl-1-propanone (<B>5</B>) were studied by means of NMR spectroscopy, mostly with the aid of the computer-simulation of the lanthanoid-induced shifts. It has been suggested that the rotamers in which the tolyl group lies close to the phenyl group are preferred in the conformational equilibria of (<I>RS</I>⁄<I>SR</I>)-<B>3</B>, <B>4</B>, and <B>5</B>. For(<I>RR</I>⁄<I>SS</I>)-<B>3</B>, the most stable rotamer (in CDCl<SUB>3</SUB>) has been suggested to have the tolyl group <I>anti</I> to the phenyl group and <I>gauche</I> to the methyl group. The results have been discussed in view of the general occurrence of the folded conformation.

• 公益社団法人 日本化学会の論文

著者

• Kunieda Norio

  Department Of Applied Chemistry Faculty Of Engineering Osaka City University

• Hirota Minoru

  Department Of Animal Science Obihiro University Of Agriculture And Veterinary Medicine

• Nishio Motohiro

  Central Research Laboratories, Meiji Seika Kaisha, Ltd.

• Endo Hiroko

  Department of Applied Chemistry, Faculty of Engineering, Yokohama National University

• Kodama Yoshio

  Central Research Laboratories, Meiji Seika Kaisha Ltd.

• Nishio Motohiro

  Central Research Laboratories, Meiji Seika Kaisha Ltd.

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