Synthesis of new bis-diphenyl-22-and diphenyl-11-membered ring N-pivot lariat crown ethers

Abstract

Bis-diphenyl 22 and 11-Membered Ring N-pivot lariat Crown Ethers^[1,2] were prepared by one step reaction of 2,2′-dihydroxy-diphenyl with N-tosyl-diethanolamine ditoskylate in DMF at refluxing temperature under N₂, Using anhydrous potassium carbonate as condensing agent, respectirely. The tosyl group of (1,2) were removed by treatment with 40% HBr in AcoH in the presence gf a large amount of phenol to give correspondence crown ether compounds (3,4). New N-pirot lariat crown thers (5,6) were prepared by one step reaction of (3) with RBr (R=−CH₂CH=CH₂, −CH₂(CH₂)₁₄CH₃) in CH₃CN at, refluxing temperature under N₂, Using anhydrous K₂CO₃ as condensing, agent. New N-pivot lariat croon ether(7) were prepared by one step reaction (4) withn-bromohexadecane in CH₃CN at refluxing temperature under N₂, Using anhydrous potassium carbonate as condensing agent. New compounds (1,3,5,6,7) were characterized by IR,¹H NMR, Ms and elemental analysis.