Skip to main content
SpringerLink
Log in

The polymerization of 3-methyl-N-(phenylsulfonyl)-1-aza-1,3-butadiene

  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Summary

A study of the polymerizability of the first crystalline 1-azabutadiene carrying an electron-withdrawing group on nitrogen is described. A convenient one-step synthesis of 3-methyl-N-(phenylsulfonyl)-1-aza-1,3-butadiene (MPAB) from methacrolein and benzenesulfonamide using titanium tetrachloride and triethylamine led to a crystalline azabutadiene monomer in good yield. With anionic initiators the monomer readily oligomerized to materials in which MPAB has reacted in a 4,1-fashion. Under radical conditions the monomer did not homopolymerize, but did copolymerize with styrene monomers to polymers with molecular weights up to 10,000. These radical copolymerizations involved exlusive 4,3-propagation (vinyl) for the azadiene monomer.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Hall, H.K., Jr., Makromol. Chemie. Symp. Ser., (1992) in press.

  2. Kitayama, T.; Hall, H.K., Jr., Macromolecules, 20, 1451 (1987).

    Google Scholar 

  3. Kim, J.B. and Hall, H.K., Jr., Macromolecules, 21, 1547 (1988).

    Google Scholar 

  4. For example: Jung, M.E. and Choi, Y.M., J. Org. Chem., 56, 6729 (1991); Teng, M. and Fowler, F. W., J. Org. Chem., 55, 5646 (1990); “Hetero Diels-Alder Methodology in Organic Synthesis”, D.L. Boger and S.M. Weinreb, Eds., Academic Press, San Diego 1987.

    Google Scholar 

  5. Boger, D.L.; Corbett W.L.; Curran, T.T.; Kasper, A.M., J. Am. Chem. Soc., 113, 1713 (1991).

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Benjamin A. Bonner, Anne Buyle Padias & H. K. Hall Jr.

Authors
  1. Benjamin A. Bonner
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anne Buyle Padias
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. K. Hall Jr.
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bonner, B.A., Padias, A.B. & Hall, H.K. The polymerization of 3-methyl-N-(phenylsulfonyl)-1-aza-1,3-butadiene. Polymer Bulletin 28, 517–523 (1992). https://doi.org/10.1007/BF00296041

Download citation

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00296041

Keywords

Search

Navigation