The preparation of crown ethers containing dicinnamoyl groups and their complexing abilities

The reaction of 1, 10-bis[p-[2-(chloroformyl)vinyl]phenyl]-1,4,7,10-tetraoxadecane with the dipotassium salt of catechol in the presence of a catalytic amount of 18-crown-6 in benzene gave 5,6-benzo-4,7,17,20,23,29-hexaoxa[10.10]paracyclopha-1,5,9-triene-3,8-dione (10a) in 3.6% yield. Also, 24,25-benzo-1,4,7,10,13,23,26-heptaoxa[13.10]paracyclopha-20,24,28-triene-22,27-dione (10b) and 27,28-benzo-1,4,7,10,13,16,26,29-octaoxa[16.10]paracyclopha-23,27,31-triene-25,30-dione (10c) were obtained by the same method in 3.1 and 3.0% yields, respectively. Irradiation of the acetonitrile solutions of the crown ethers, 10a, 10b and 10c, by Pyrex-filtered UV light (>300 nm) gave the corresponding intramolecular [2+2]photocycloadducts, 11a, 11b and 11c, in 95.8, 93.2 and 90.1% yields, respectively. The structures of 11a, 11b and 11c were confirmed to be the β-form by their 1H NMR spectra. The photoreversible cleavage of 11a, 11b and 11c by 220 nm UV light gave the corresponding starting crown ethers, 10a, 10b and 10c,...

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