4.4 Article

The Regiospecific Preparation of 2-Substituted Tribenzotriquinacenes

Journal

SYNLETT
Volume 24, Issue 4, Pages 453-456

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1318143

Keywords

cuplike aromatics; Friedel-Crafts cyclizations; cyclo-eliminations; convex molecules; chiral aromatics; double-cup structures; single-crystal X-ray structural analysis

Funding

  1. Fonds der Chemischen Industrie
  2. Studien-stiftung des deutschen Volkes
  3. INDIGO program

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Several substituted tribenzotriquinacene derivatives (TBTQ) carrying functional groups exclusively in the 2-position (OMe, OH, Br, CHO, CN, styryl, etc.) have been prepared by our new synthesis of the tribenzotriquinacene framework. The route has been extended to the preparation of a double-cup molecule in which two TBTQ moieties are fused by a benzene ring. The trans configuration of one of the diastereomers of this hydrocarbon was established by X-ray structural analysis.

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