Regioselection in the synthesis of 4-benzyltetral-1-ones and the new 4-arylbenzosuber-1-ones

Daniel Truong, Brittany L. Howard, Philip E. Thompson

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The intramolecular Friedel-Crafts acylation of 4,5-diarylpentanoic acids has the possibility to cyclise to either a 6-membered ring to give 4-benzyltetral-1-one or a 7-membered ring to give 4-arylbenzosuber-1-one. Of these, only the former compound class has previously been reported. The impact of the substituents positioning on the outcome of the cyclisation has been investigated. The complete formation of either the tetralone or the benzosuberone regioisomer was possible under the same reaction conditions, dependent upon the ring activation and/or deactivation of the chosen substituents. Selected bromo or methoxy substituents could be used as auxiliaries, included in precursors to afford the desired regioisomer and then subsequently removed.

Original languageEnglish
Article number132034
Number of pages13
JournalTetrahedron
Volume85
DOIs
Publication statusPublished - 9 Apr 2021

Keywords

  • Benzosuberone
  • Cyclisation
  • Friedel-Crafts acylation
  • Regioselectivity
  • Tetralone

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