Study On The Synthesis And Preliminarily Polymerization Of α,β-Unsaturated Amides Derived From Menthone Oxime

Poly(triphenylmethyl methacrylate) (poly(TrMA)) exhibit high chiral recognition. However, the ester groups of poly(TrMA) are slowly solvolyzed. Therefore, it is highly desirable to prepare the helical polymer, which is durable against the solvolysis and exhibit high chiral recognition. Helical poly(α,β-unsaturated amides) which have been reported previously are not suitable for chiral recognition though they are against the solvolysis. We expect to design and to synthesis new helical poly(α,β-unsaturated amide)s which possess all the advantages mentioned above.In this paper, new unsaturated amide monomers, (3R,6S)-1-acryloyl-6-isopropyl- 3-methylazepan-2-one, (3R,6S)-1-methacryloyl-6-isopropyl-3-methylazepan-2-one, (2S,5R)-1-acryloyl-2-isopropyl-5-methylazepane, (2S,5R)-1-methacryloyl-2-isopropyl -5-methylazepane, N-isopropyl-N-menthyl-methacrylamide were synthesized and had been tentatively polymerized by anionic polymerization and radical polymerization. The polymerization produced unfavourable results.As for some reactions in this paper, we have simply discussed their regioselectivity and stereoselectivety.Because of the umbrella effect of N atom, the 13C NMR signals of N-acryl (2S,5R)-2-isopropyl-5-methylazepane and N-isopropyl-N-menthyl-methacrylamide were doubled yet the signals of N-acryl (3R,6S)-6-isopropyl-3-methylazepan-2-one were not doubled.