Preparation, absolute configuration and conformation of some .ALPHA.-aryl-2-pyridylmethanols.
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概要
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The syntheses of five optically active α-aryl-2-pyridylmethanols <B>1–5</B> are described. It is shown by means of chemical correlation with the known (−)-(α<I>R</I>,2<I>S</I>)-α-phenyl-2-piperidylmethanol <B>6</B> that all levo-rotatory isomers of <B>1–4</B> are of R configuration. It is also found via the relative integral intensities in the infrared spectra of the bands due to free and intramolecularly bonded hydroxyl groups in the compounds <B>1–4</B> and the free hydroxyl groups in the model compounds <B>7–10</B>, that the population of the conformers with an intramolecular OH···N bond in compounds <B>1–4</B> exceeds 80%.
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