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t-BuOK reacts with cationic 18-electron d 6 Fe II complexes of aryl ethers ArOR as their PF6 - salts to cleave the C-O bond of the aryl ether, yielding Fe II –hexahapto-phenolate complexes and the ethers t-BuOR, only in the presence of a salt, the best one being [n-Bu4N][PF6]. Salt effects in THF result from either enhancement of nucleophilic reactivity of t-BuO - with a large cation or polarization of the aryl ether C-O bond with a THF-insoluble salt such as KBr or NaCl. This nucleophilic reaction of t-BuO - is of special interest for the 8-step synthesis of a triallyl phenol dendron obtained when the cleavage reaction of the complexes of aryl ethers is carried out in the presence of allyl bromide. During this reaction that is carried out without addition of a salt, it is the in situ formation of KBr during the three deprotonation-allylation sequences that further facilitates the crucial aryl ether cleavage at low temperature.

Can t-BuOK be a good nucleophile? An ion-pairing answer. Cleavage of aryl ethers in their cationic iron complexes