Free‐radical addition of perfluoroalkyl iodides (RFI) to diallylcyanamide gave cis‐ and trans‐1‐cyano‐3‐iodomethyl‐4‐(perfluoroalkyl)methylpyrrolidine (Ia,b). Five‐membered ring products were preferentially formed in this reaction by other 1,6‐dienes having terminal vinyl groups. This strongly suggests that cyclopolymerization of such monomers occurs in analogous fashion, instead of leading to 6‐membered rings as has been previously understood. Dehydrohalogenation of Ia,b gave 3‐methylenepyrrolidine derivatives as expected. Infrared and NMR spectra clearly show the exocyclic CH2 group. The influence of reaction conditions on the yield of cyclization product Ia,b and certain side products was investigated.
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Neal O. Brace (1970) studied this question.
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