CHEMISTRY: Air to the Rescue

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Science  22 Feb 2008:
Vol. 319, Issue 5866, pp. 1013a
DOI: 10.1126/science.319.5866.1013a

Chemists generally take pains to ensure the purity of their reagents, lest a highly reactive contaminant doom the anticipated outcome. Once in a while, though, an adventitious impurity proves more help than hindrance. The reported synthesis of quinine by Woodward and Doering in 1944 was a landmark achievement in the history of organic chemistry, but in the ensuing years, controversy swelled over the report's reliance on a final reduction step published 26 years earlier by Rabe and Kindler. Was the chemistry in this last step really viable? Had Woodward taken his synthesis all the way to fruition, or actually stopped at the penultimate step? In a meticulous effort to reproduce the Rabe study, Smith and Williams now find that modern concerns probably arose on account of excessively pure materials. They show that the reduction proceeds most efficiently when the aluminum powder called for in the published procedure has been partially oxidized by exposure to air, a reasonably likely circumstance in 1918. — JSY

Angew. Chem. Int. Ed. 47, 1736 (2008).

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