Cyclopolymerization. IV. Low Molecular Weight Products for the Reactions of Allylamines and Diallylamines with Azobisisobutyronitrile
- 1 January 1975
- journal article
- research article
- Published by Taylor & Francis in Journal of Macromolecular Science: Part A - Chemistry
- Vol. 9 (1) , 149-167
- https://doi.org/10.1080/00222337508068652
Abstract
The azobisisobutyronitrile-initiated polymerization of various N-substituted diallylammonium, N-ethyldimethallylammonium, and triallylammonium chlorides yielded as the respective major by-products 2-substituted 6, 6-dimethylperhydro-5-isoindolones, 2-ethyl-3a, 6,6,7a-tetramethylperhydro-5-isoindolone, and 2-allyl-6,6-dimethylperhydro-5-isoindolone. These isoindolones are formed from pyrrolidylmethylene radical precursors and indicate that, in agreement with recent ESR studies, radical addition to diallylamines results in the formation of pyrrolidine derivatives and not piperidines as previously supposed. The reactions of azobisisobutyronitrile and azobisis-obutyramidine dihydrochloride with the models, N,N-dimethylallylammonium and N,N,2-trimethylallylammonium chlorides, are also described.Keywords
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