Reactions of perfluoroalkyl iodides with styrene and its derivatives were investigated under radical conditions in the presence of oxygen. The photochemical reaction of styrene with CF3(CF2)5I in the presence of tributyltin hydride or tris(trimethylsilyl)silane under an oxygen atmosphere afforded the corresponding perfluoroalkylated alcohols in moderate yields together with CF3(CF2)5H. However, the photochemical reactions of styrene and its derivatives with CF3(CF2)nI (n = 3, 5) in the presence of hexabutylditin under oxygen produced the perfluoroalkylated alcohols in good yields. Furthermore, the reactions of styrenes with CF3(CF2)nI (n = 3, 5, 9) and Na2S2O4 in the presence of a base under air formed the same alcohols in good yields. The alcohols were found to provide a novel type of α-fluoroalkylated styrenes by acidic dehydration. Perfluoroalkylated α,β-unsaturated ketones were synthesized by oxygenative perfluoroalkylations of α-chlorostyrene and its derivatives using CF3(CF2)nI (n = 3, 5) under radical reaction conditions. The ketones were found to be good synthetic building blocks for perfluoroalkylated heterocycles, such as pyrazoles, dihydrodiazepines, pyrimidines, and isoxazoles.

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A macrocyclic hexaketone monohydrate was synthesized by the oxidation of either tribenzohexadehydro[12]annulene or tribenzotetradehydro[12]annulene-1,2-dione with ruthenium catalysts; the hexaketone monohydrate incorporates small molecules with a hydroxy, carbonyl or ether group in the crystalline lattice to form inclusion complexes.

The cyclic [5]meta-phenyleneacetylene (3) ([5]CMPA) and its corresponding cyclophane polyones 4 and 5 are synthesized. 3, a “missing link” between [4]CMPA and [6]CMPA, shows a fairly pronounced emission, indicating a rigid structure, whereas 5 is colorless in contrast to conventional diarylethane-1,2-diones owing to its conformational mobility and all-s-cis and twisted dione structure.