SYNTHESIS OF NEW BENZOSULFOXIDE MACROCYCLIC COMPOUNDS

Abstract

Bis(dibenzosulfoxo)-27,30,35,38-tetramethyl-24-crown-6, bis(dibenzosulfoxo)-21,24,29,32-tetramethyl-18-crown-4, dibenzosulfoxo-15,18-dimethyl-12-crown-3 and dibenzosulfoxo-12,15-dimethyl-9-crown-2 macrocycles are synthesized by the reaction of 2,2′-sulfinyl-bis(4-methyl phenol)and 1,2-dibromoethane and diethyleneglycol di-p-toluenesulfonate.

Keywords:

• Benzosulfoxide
• crown ether
• macrocycle
• template effect

Notes

Synthesis of the substrate 1 as 2,2′-Sulfinyl bis(4-methyl phenol): To a cold suspension of anhydrous aluminum chloride (25 g, 0.187 mmol) in 100 ml of dichloromethane p-cresol (20 g, 19.34 cc, 0.185 mmol) in 50 ml of dichloromethane was added portionwisely.