Interaction | Reaction | Process     Data Page

The Tascher-Eschenmoser method for cleaving methyl esters involves the direct nucleophilic attack of (soft) iodide ion upon the (soft delta+) methyl function.

Carboxylate ion acts as the nucleofugal leaving group. Solvent is usually anhydrous pyridine.

Chapter 15: Addition to carbon-carbon multiple bonds. J.March, Advanced Organic Chemistry, J. Wiley & Sons, Third Edition, 1985
  +  
I–
  +  
Li+
  +  
         
RCOO–
  +  
Li+
  +  
CH3I
Reactant Page Go To Go To
Methyl ester (generic)     Reactions Using    Reactions Forming
Iodide ion     Reactions Using    Reactions Forming
Lithium ion     Reactions Using    Reactions Forming
Pyridine Solvent    Reactions Using    Reactions Forming
Carboxylate ion (generic)     Reactions Using    Reactions Forming
Lithium ion     Reactions Using    Reactions Forming
Methyl iodide     Reactions Using    Reactions Forming

Interaction, Reaction, Process defined as:
Alkylation
Substitution: Nucleophilic Second Order

© Mark R. Leach 1999 –

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