Abstract
Polymerization of o-formylphenylacetaldehyde was carried out with various catalysts. The polymer obtained below −60°C with BF3OEt2 catalyst was soluble in common organic solvents and was confirmed as a cyclopolymer composed of 6-membered cyclized units. The cationic cyclization step in the cyclopolymerization of o-formylphenylacetaldehyde was inferred to proceed through a intermediate or concerted scheme similar to those proposed for the cationic propagation of o-phthalalde-hyde.On the other hand, under cationic polymerization conditions over −40°C o-formylphenylacetaldehyde gave a cyclic trimer (mp 284–285°C) possessing fused ring ether, which had no aldehyde group. Interestingly, the cyclic trimer was also produced from the polymer by treatment with BF3OEt2 in methylene dichloride.Cyclopolymers of o-formylphenylacetaldehyde were also obtained with Ziegler catalyst at 0 and −78°C, and with t-BuOLi catalyst at −78°C.
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Tagami, S., Kagiyama, T. & Aso, C. Polymerization of Aromatic Aldehydes. VII. Cyclopolymerization of o-FormylphenylacetaIdehyde and Formation of a Cyclic Trimer. Polym J 2, 101–108 (1971). https://doi.org/10.1295/polymj.2.101
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DOI: https://doi.org/10.1295/polymj.2.101