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Synthesis of aminimide monomers and polymers

✍ Scribed by Mehta, Avinash C. ;Rickter, Donald O. ;Kolesinski, Henry S. ;Taylor, Lloyd D.

Publisher
John Wiley and Sons
Year
1983
Weight
357 KB
Volume
21
Category
Article
ISSN
0360-6376

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✦ Synopsis

Abstract

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.

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