Poly-β-Amino Acids. I. The Preparation of Phenyl Substituted β-Amino Acid Polymers

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α-Phenyl-, β-phenyl-, and α,β-diphenyl-β-aminopropionic acid were synthesized. Their polymers were obtained in good yields when the <I>p</I>-nitrophenyl esters of β-amino acids were polymerized at 60°C. The ethyl esters gave low-molecular-weight polymers in poor yields at 150°C <I>in vacuo</I>. By the thermal polycondensation of β-amino acids themselves at 250°C, polymers were not obtained, but the corresponding cinnamic acid derivatives were obtained by the intramolecular β-elimination reaction. Poly(α-phenyl-β-amino acid), and poly(β-phenyl-β-amino acid) were soluble in trifluoroacetic acid, and chloroform containing a small amount of dichloroacetic acid. On the other hand, poly(α,β-diphenyl-β-amino acid) was soluble only in cone, sulfuric acid, while it was insoluble in usual organic solvents. The DP of poly(β-phenyl-β-amino acid) was about 18. None of the polymers showed any melting point below 300°C.
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