Ferrocene compounds. XXV. Synthesis and characterization of ferrocene-containing oligoamides, their precursors, and analogues

Abstract

A general method for preparation of ferrocene-containing monoamines (5–7) and diamines (10, 11) starting from the corresponding quaternary ammonium iodide 3 and ferrocene mono- (4) and dithiaaliphatic acids (8, 9) was developed. Amines obtained have been characterized as acet- and benzamides (12–15). The oligoamide precursors (16, 17, 22, 23) were synthesized by reactions of succinic or glutaric anhydride with amines (6, 7, 10, 11). Their conversion into oligoamide analogs (20, 21, 25) failed. The desired diamides (20, 21) were prepared by condensation of amines (6, 7) with alkanedioyl chlorides, (CH2)n(COCl)2 (n = 0, 1, 2, 3). Reactions of diamine 10 with succinic or glutaric anhydride gave amino acids 28—formal monomers for the planned oligomerization. Oligomers 29 were synthesized by condensation of equimolar amounts of diamines 10 and the above mentioned alkanedioyl chlorides in dichloromethane at 0°C. The structure of oligomers 29 was indicated from their IR and 1H-NMR spectra in comparison with the model substances 12–28. The degree of polymerization of compounds 29 was determined by 1H-NMR end-group analysis (DPn = 4–6). © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 25–36, 1999