Summary
Monomer (1-trimethylsilyl-ethinyl)-(1-methyl-vinyl) ketone 1 was synthesized to study the reaction behaviour in radical reactions. Not only is the vinyl double bond very effective to react with radicals but also is the triple bond. At higher conversions insoluble polymers are formed. In dilatometer experiments with styrene monomer 1 proved to be an effective retarder rather than a transfer agent. To elucidate the mechanisms envolved in monomer 1 radical reactions, model compound (1-trimethylsilyl-ethinyl)-phenyl ketone 5 was synthesized and investigated in comparision.
Similar content being viewed by others
References
L.E. Coleman, Jr., N.A. Meinhardt, Fortschr. Hochpolym.-Forsch. 1, 159 (1959)
R.V. Subramanian, Adv. Polym. Sci 33, 35 (1979)
N. Yamashita, H. Inoue, T. Maeshima, J. Polym. Sci., Polym. Chem. Ed. 17, 2739 (1979)
R.C. Schulz, G. Wegner, W. Kern, J. Polym. Sci. Part C 16, 989 (1967)
P. Schulz, W. Strobel, Monatsh. Chem. 99, 1742 (1968)
O.W. Webster, W.R. Hertler, D.Y. Sogah, W.B. Farnham, T.V. Rajan Babu, J. Am. Chem. Soc. 105, 5706 (1983)
Houben-Weyl, Methoden der Organischen Chemie, E 20, Georg Thieme Verlag, Stuttgart, 1987, p. 153–216, 1173–1174
O.W. Webster, D.Y. Sogah, in “Recent Advances in Mechanistic and Synthetic Aspects of Polymerization”, M. Fontanille, A. Guyot, Eds., Nöto Asi Series, Dordrecht, 1987
O.W. Webster, Polym. Prepr. 27, 161 (1986)
C. Willis, R.A. Back, R.H. Morris, Can. J. Chem. 55, 3288 (1977)
M. Malacria, M.L. Roumestant, Tetrahedron 33, 2813 (1977)
J.M. Hay, Reactive Free Radicals, Academic Press Inc., London, 1974
Author information
Authors and Affiliations
Additional information
Dedicated to Prof. Dr. Harald Cherdron on the occassion of his 60th birthday
Rights and permissions
About this article
Cite this article
Hallensleben, M.L., Marchig, C. Synthesis and radical reaction behaviour of (1-trimethylsilyl-ethinyl)-(1-methyl-vinyl) ketone. Polymer Bulletin 27, 367–374 (1992). https://doi.org/10.1007/BF00309691
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00309691