Summary
The paper deals with the synthesis of the phenylazo-formamidoethyl 4-t-butylazo-4-cyanovalerate, a product which — by its two azo groups having different thermal stabilities — may be used in initiating processes of stepwise radicalic polymerization. The preparation is based on the condensation of the 4-t-butylazo-4-cyanovaleric acid chloride with N-hydroxy ethyl-phenylazoformamide (HEPF) in anhydrous chloroform, in the presence of pyridine. The initiator purification involves its passing over an alumina column, on using methylene chloride as eluent. HEPF is a new intermediate obtained by the reaction of the ethyl phenylazocarboxylate with ethanolamine. Both the HEPF structure and that of the bis-azo initiator is confirmed by elemental analysis and spectroscopic measurements (IR and H-NMR spectra), as well.
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Simionescu, C.I., Comanita, E., Pastravanu, M. et al. Bifunctional initiators: synthesis of phenylazo-formamidoethyl 4-t-butylazo-4-cyanovalerate. Polymer Bulletin 18, 13–17 (1987). https://doi.org/10.1007/BF00255816
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DOI: https://doi.org/10.1007/BF00255816