Polymeric chiral crown ethers, 2. Syntheses and chiral recognition of polymers consisting of (S)‐ or (R)‐2,2′‐binaphthyl‐21‐crown‐6 units through cyclopolymerization of divinyl ethers

Optically active divinyl ethers, (−)‐(S)‐ and (+)‐(R)‐2,2′‐bis[2‐(2‐ vinyloxyethoxy)ethoxy]‐1,1′‐binaphthyl [(S)‐1 and (R)‐1], were synthesized and polymerized with cationic catalysts. The resulting polymers are composed of only cyclic constitutional units, (S)‐ and (R)‐dinaphtho‐[2,1‐r:1,2‐t]‐1,4,7,11,14,17‐hexaoxaperhydrocyclohenicosen‐8,10‐ylene. Both (S)‐ and (R)‐polymers show nearly equal values of optical rotation, but in opposite directions. The ability of chiral recognition of the (R)‐polymer towards racemic primary alkylammonium salts was investigated with salts of 1‐phenylethylamine, valine, phenylalanine and phenylglycine, and found to be very similar to that of the corresponding model crown ether.