A Family of Bisnaphthyl C(2)-Symmetric and Asymmetric Clefts: Synthesis, Solid-State Structure, and Calculation of the Interplanar Angle

The synthesis of a new family of naphthalenoid C(2)-symmetric clefts has been realized through a four-step synthetic sequence giving three C(2)-symmetric clefts and a rare nonsymmetric example. Subsequently, stereoselective reduction of the carbonyl groups at C-8 and C-16 then provides cleft molecules with hydrogen bonding potential. Using single-crystal X-ray and computational analysis, the cleft angle of the dione has been determined.