Abstract
An equimolar reaction of acrolein oxime (AOM) and butyllithium (BuLi) was studied at 0°C in different solvents. The structure of the reaction products was determined by 13C-NMR spectroscopy and gas chromatography-mass spectrometry. Lithium acrolein oxime was formed as the main product. When the reaction mixture was treated with dilute hydrochloric acid, about 80% of the AOM was recovered and many other products, such as heptanal oxime, 2-methylhexanal oxime, butyl vinyl ketone oxime etc., were obtained in different yields depending on the kind of solvent used; BuLi can add to the head or tail of the vinyl group and to the oxime group, of AOM. The initial processes of AOM polymerization by BuLi are explained on the basis of the reaction products.
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References
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Ota, T., Tanaka, M., Asahi, Y. et al. Studies on the Polymerization of Acrolein Oxime. XI. Equimolar Reaction of Acrolein Oxime and Butyllithium. Polym J 12, 1–7 (1980). https://doi.org/10.1295/polymj.12.1
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DOI: https://doi.org/10.1295/polymj.12.1
