ISSN:
0360-6376
Keywords:
Physics
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A convenient and practical synthesis of trimethylamine acrylimide, 1, starting from 1, 1, 1-trimethylhydrazinium p-toluenesulfonate, 3, and 3-chloropropionyl chloride is described. The intermediate, trimethylamine 3-chloropropionimide, 2, is easily transformed into 1 either through a single-step dehydrohalogenation or through a two-step process consisting of very facile thermal rearrangement to 1,1,1-trimethylacrylylhydrazinium chloride, 4, and subsequent deprotonation. Two new polymerizable monomers, 5, and 6, containing aminimide functionality were synthesized from trimethylamine imine, 7, and the appropriate vinyl oxazolones, 8, and 9. Synthesis of hitherto unreported trimethylamine chloroacetimide, 10, which offers unique opportunities for incorporating water-solubilizing and alkali-stable aminimide functionality into a variety of structures through nucleophilic displacement, is also described.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/pol.1983.170210422
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