This document details the Mitsunobu reaction, a pivotal organic transformation used to convert primary/secondary alcohols into esters, ethers, or thioethers via SN₂ mechanism. Key features include:
Reagents: Triphenylphosphine (TPP) and diethyl azodicarboxylate (DEAD) or DIAD.
Mechanism: Involves protonation of the nucleophile and inversion of alcohol stereochemistry.
Applications:
Synthesis of esters, phenyl ethers, and thioethers.
Oxygen isotope labeling for studies.
Preparation of complex molecules (e.g., aziridines, morphine derivatives, oseltamivir).
Nucleophile requirement: Must be acidic to facilitate protonation during the reaction.
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