Phase-transfer catalysis poisoning

Tosylate is displaced by weak oxyanions with little elimination in aprotic solvents, providing alternative routes to polymer-bound esters and aryl ethers. Alkoxides, unfortunately, give significant functional yields of (vinyl)polystyrene under the same conditions. Phosphines and sulfides can also be prepared from the appropriate anions (57), the latter lipophilic enough for phase-transfer catalysis free from poisonning by released tosylate. 

Bar, R., J. Zerda, and Y. Sasson, Kinetics in Phase Transfer Catalysis A Theoretical Study 1. Poisoning Effect by Catalyst Foreign Ion, J. Cheat Soc. Perkin Trans., 2, 1875 (1984). 

Sasson, Y., and H. A. Zahalka, Catalyst Poisoning Phenomenon in Phase Transfer Catalysis Effect of Aqueous Phase Concentration, ... 

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