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  • Physics  (2)
  • Wiley-Blackwell  (2)
  • Royal Society
  • 1
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 11 (1973), S. 1167-1176 
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The thermal decomposition of 4,4-diphenyl-Δ2-1,2,3-triazolin-5-one (I) was reinvestigated and shown to yield poly-α,α-diphenylglycine (III) instead of the previously reported 3,3,6,6-tetraphenylpiperazine-2,5-dione (II). Differentiation between the two structures was made by molecular weight determinations and spectroscopic analyses. The infrared spectra were studied in detail and compared with model compounds. They showed that the absorption peak at 1470 cm-1 must be attributed to the trans-amide II absorption of the polymer. Furthermore, the polymers were found to contain terminal CONH2 as well as triazolinone or ether functions (from alcohol). Fractionation was performed in three solvents based on solubility differences: dichloroethane (or chloroform), methanol, and n-hexane. All the fractions were characterized by physical methods. A mechanistic investigation revealed that the polymerization process cannot be rationalized by a radical or cationic mechanism, but is compatible with a molecular mechanism involving triazolinone functions at the growing chain ends.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 11 (1973), S. 1177-1183 
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 4,4-Diphenyl-Δ2-1,2,3-triazolin-5-one (I) was found to undergo a cationic polymerization under the influence of boron trifluoride etherate in an anhydrous solvent. The poly-α,α-diphenylglycine (III) thus formed contained a larger amount of oligomers than the polymer obtained by thermal decomposition as described in the preceding paper. The molecular weight distribution was further shown to depend on the monomer and catalyst concentration and on the nature of the solvent. A mechanistic rationalization is proposed, involving propagating triazolinium ion pairs (VII) which are not interrupted by chain transfer or termination in the absence of water or alcohol. In the presence of water or alcohol, no polymerization occurred, but the normal acid-catalyzed decomposition products (IV and V) were then obtained. 1-Methyl-4,4-diphenyl-Δ2-1,2,3-triazolin-5-one (VIII) was also treated with BF3 · OEt2 in a dry solvent at room temperature and furnished 1-methyl-3-phenyl-indolin-2-one (XII) instead of a polyamide. This reaction constitutes a new method for the synthesis of these heterocycles.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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