DEOXYMERCURATION

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Abstract
The conversion of several stereoisomeric oxymercurials to alkenes (deoxymercuration) has been studied with hydrogen chloride in anhydrous and near-anhydrous methanol. In each instance the addition of water decreases the second-order rate. In benzene the addition of water to the anhydrous system first accelerates and then decreases the reaction rate. These results have been interpreted in support of molecular rather than ionic participation by hydrogen chloride. Since molecular participation requires the ↑↑ arrangement of alkoxy and chloromercuri groups for easy reaction it follows that oxymercuration also follows a molecular and not a "mercurinium ion" mechanism in the normal reaction.

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