Pb83-0243-09 - compound shown over the arrow below),...

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Problem 83, Chemistry 0243 - 2009 Here's a reaction you have never seen. In fact it appears in only one textbook. It's useful and interesting, however, and makes a very nice problem: taxing but not impossible. The key is to go at it in an organized, stepwise fashion (that's true for most problems). When oxiranes (epoxides, 1 ) are treated with metal thiocyanates (don't be intimidated by the name, it's the perfectly ordinary
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Unformatted text preview: compound shown over the arrow below), thioepoxides ( 2 ) result. O S S C N M + 1 2 Provide a mechanism for this reaction and work though the stereochemical consequences if the starting material is the compound shown below: S C N M + O H 3 C CH 3 H H Useful hint: nucleophiles such as RO add reversibly to carbon-nitrogen triple bonds. R C N RO OR R C N...
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