American Chemical Society
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A Family of Bisnaphthyl C2‑Symmetric and Asymmetric Clefts: Synthesis, Solid-State Structure, and Calculation of the Interplanar Angle

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journal contribution
posted on 2023-02-28, 22:13 authored by Gazalah S. Mohammed Elgadi, Mark R. J. Elsegood, Miheal Patel, Paulo. A. Netz, Tiago E. de Oliveira, Marc C. Kimber
The synthesis of a new family of naphthalenoid C2-symmetric clefts has been realized through a four-step synthetic sequence giving three C2-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.