Preparation and Properties of Amphiphilic Compounds Containing (η⁴-Diene) tricarbonyliron as a Lipophilic Group

Abstract

Synthetic routes were established for amphiphilic compounds containing (η⁴-diene) Fe (CO) ₃ as a lipophilic group and ammonium or sulfonium group as a hydrophilic group from 2, 4-hexadienoic acid and Fe (CO) ₅ as starting materials. The ammonium salt, [CH₃CH=CHCH=CHCO₂ C₆H₄N⁺Me₃] Fe (CO) ₃I^- (3) and sulfonium salt [CH₃CH=CHCH=CHCO₂C₆H₄S⁺Me₂] Fe (CO) ₃ MeSO₄^- (7) thus obtained were found soluble in water and polar organic solvents and stable in solvents.
Reaction of (3) and (7) with amines in water-acetonitrile solution led to the conversion of the ester group to an amide group in good yield. The reaction of (3) with octylamine was depended on the water/acetonitrile ratio of the solvent. The yield of amide was maximum at a water/acetonitrile ratio of 3. Equilibrium between the ammonium salt and its free amine would appear to be the cause for the solvent effects. However, amide yield in the reaction of (7) with ocatylamine was virtually constant regardless of the solvent ratio.