Alkoxy-mercuration of Alkenes

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Jan 23, 2023
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- Synthesis of Ethers
- Dehydration of Alcohols to Make Ethers

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The alkoxymercuration reaction is similar to oxymercuration reaction, except alcohol is used instead of water.

Reactions #3 and #4 are examples of this two-step procedure. Note that the alcohol reactant is used as the solvent, and a trifluoroacetate mercury (II) salt is used in preference to the acetate (trifluoroacetate anion is a poorer nucleophile than acetate). The mechanism of alkoxymercuration is similar to that of oxymercuration, with an initial anti-addition of the mercuric species and alcohol being followed by reductive demercuration.

Contributors

William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry

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