Tris(polyoxaalkyl)amines (Trident), a New Class of Solid-Liquid Phase-Transfer Catalysts

Article abstract of DOI:10.1021/jo00220a009

A new class of solid-liquid phase-transfer catalysts has been prepared.These tris(polyoxaalkyl)amines (I) are designed to obtain the best balance between straightforward synthesis (cheap starting materials), high activity, easy recovery, and low toxicity.The catalysts are synthesized from ethylene glycols by a simple one-step method in yields in the range of 65-81percent.They show high catalytic effects in aliphatic nucleophic substitutions and aromatic nucleophilic substitutions on activated and unactivated molecules.In the Ullman synthesis (a new PTC reaction) there is a synergic effect of anionic activation by tridents and by copper salts.Reactions have been carried out at temperatures up to 180 deg C without evidence of decomposition of the tris(polyoxaalkyl)amines. The behavior and catalytic activity of these catalysts are discussed.