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Cooperative Brønsted acid-type organocatalysis: alcoholysis of styrene oxides

Torsten Weil1, Mike Kotke, Christian M Kleiner

  • 1Institut für Organische Chemie, Justus-Liebig-Universität, Heinrich-Buff-Ring 58, Giessen, Germany.

Organic Letters
|March 28, 2008
PubMed

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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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