Mechanistic investigation of superelectrophilic activation of 1,1′-bi-2-naphthols in the presence of aluminum halides

Zhongwei Zhu, Alexander M. Genaev, George E. Salnikov, Konstantin Yu Koltunov

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

7,7′-Dihydroxy-1,1′-bi-2-naphthol, as a result of superelectrophilic activation in the presence of an excess of aluminum halides, reacts with cyclohexane and benzene to yield 5,6,7,8,5′,6′,7′,8′-octahydro-7,7′-dioxo-bi-2-naphthol and its 5,5′-diphenyl derivative, respectively. In contrast, isomeric 6,6′-dihydroxy-1,1′-bi-2-naphthol does not react at all under the same reaction conditions, while the parent 1,1′-bi-2-naphthol (BINOL) reveals an alternative mode of behavior. The mechanistic aspects of these intriguing results are discussed on the basis of experimental and theoretical (DFT) study of the protonation and complexation properties of the starting BINOLs.

Original languageEnglish
Pages (from-to)3971-3977
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number16
DOIs
Publication statusPublished - 17 Apr 2019

Keywords

  • IONIC HYDROGENATION
  • BINOL
  • CYCLOHEXANE
  • ACID
  • NAPHTHALENEDIOLS
  • CONDENSATION
  • BENZENE

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