Synthesis of Rigid and Optically Active Bis(binaphthyl) Cyclic Compounds

Abstract

Optically active cyclic bis(binaphthyl)s (4a -d), which are composed of aromatics, ethers, and ketonic carbonyls, were synthesized through a two-step nucleophilic aromatic substitution reaction. Bis(binaphthyl) cyclic compounds (4a and 4b) were obtained in moderate yields when difluoride 3a and 3b were employed. On the other hand, bis(binaphthyl)s 4c and 4d were scarcely obtained when 3c and 3d were employed.

Synthesis of Wholly Aromatic Polyketones Containing Optically Active Macrocycles

“…18 Introduction of these cyclic aromatic bis(binaphthyl)s to polyketone backbones will produce polyketones with optically active cavities in the main chains.…”

“…14,15,18 Next, reaction of difluoride 3 with 4-chlorobenzoic acid (4a) was carried out in P 2 O 5 -MsOH. 19 According to our previous report, 11 the reaction at 80 C afforded the corresponding disubstituted binaphthyl (5a) in good yield.…”

Synthesis of aromatic poly(ether ketone)s bearing optically active macrocycles through Suzuki coupling polymerization

“…Furthermore, we developed aromatic polyketones containing optically active macrocycles [9][10][11][12][13] composed of 1,1¢-binaphthyl-2,2¢-dioxy units. 14,15 These macrocycle-bearing polymers have adequate thermal and optical properties and solubility for use in engineering applications.…”