Moribe Taito, Hirano Junichiro, Takano Hideaki, Shinokubo Hiroshi, Fukui Norihito
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan.
Institute for Advanced Research, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan.
Beilstein J Org Chem. 2025 Jul 14;21:1454-1461. doi: 10.3762/bjoc.21.107. eCollection 2025.
Cyclobisbiphenylenecarbonyl (CBBC) represents a readily available chiral figure-eight macrocycle containing two carbonyl groups. However, the transformation of the carbonyl groups has been unexplored. Herein, we conducted the Wittig reaction of CBBC with methylenetriphenylphosphorane to furnish two chiral macrocycles containing one or two exocyclic olefin units. Owing to the transformation of carbonyl groups, the resulting products exhibit several unique physical and chemical properties: (1) the enhancement of configurational stability, (2) the appearance of fluorescence, and (3) the reductive carbon-carbon-bond formation between carbonyl and alkene units.
环双亚苯基羰基（CBBC）是一种易于获得的含有两个羰基的手性8字形大环化合物。然而，羰基的转化尚未得到探索。在此，我们进行了CBBC与亚甲基三苯基磷烷的维蒂希反应，以提供两个含有一个或两个环外烯烃单元的手性大环化合物。由于羰基的转化，所得产物表现出几种独特的物理和化学性质：（1）构型稳定性增强，（2）荧光出现，以及（3）羰基和烯烃单元之间形成还原性碳-碳键。
