Exploration of the Mitsunobu Reaction with Tosyl- and Boc-Hydrazones as Nucleophilic Agents

Tosyl- and Boc-hydrazones were found to be effective nucleophiles in the Mitsunobu reaction. Tosyl hydrazones reacted cleanly with primary and secondary alcohols when co-administered to a cooled DBAD/PPh₃ or DEAD/PPh₃ complex. Boc-hydrazones required electron-withdrawing substituents to participate in the reaction.