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Polycondensation of N-Chlorobenzoquinonimines

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Summary

Self-condensations of 4-chloroimino-2, 5-cyclohexadiene-1-one 1 (benzoquinone N-chloroimine), 2-tert-butyl-4-chloroimino-2, 5-cyclohexadiene-1-one 2, and 3-tert-butyl-4-chloroimino-2, 5-cyclohexadiene-1-one 3 in N-methylpyrrolidinone containing inorganic bases have been investigated. Monomer 1 gave polymers having inherent viscosities of 0.27–0.33 dLg−1. Monomers 2 and 3 only gave oligomers. 1H NMR spectra suggest that polymerization of 1 mainly occurs at C-2 and C-6 positions. A Michael-type addition mechanism, based on the high α-effect nucleophilicity of =NCl, is proposed.

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Authors and Affiliations

  1. C.S. Marvel Laboratories, Chemistry Department, University of Arizona, 85721, Tucson, AZ, USA

    Yen-Yuan Chen & H. K. Hall Jr.

Authors
  1. Yen-Yuan Chen
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  2. H. K. Hall Jr.
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Chen, YY., Hall, H.K. Polycondensation of N-Chlorobenzoquinonimines. Polymer Bulletin 20, 37–44 (1988). https://doi.org/10.1007/BF00262247

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