Base mediated aromatization of carbonyl condensation products derived from 2-(2-bromoprop-2-enyl)cyclohexanone derivatives via 'intramolecular unsaturation transfer'

Yazicioglu E. Y. , Akhmedov I. M. , TANYELİ C.

HELVETICA CHIMICA ACTA, vol.91, no.6, pp.1148-1155, 2008 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 91 Issue: 6
  • Publication Date: 2008
  • Doi Number: 10.1002/hlca.200890124
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1148-1155


Alkylbenzenes are synthesized for the first time from aliphatic hydrocarbons via an one pot, transition metal-free coupling approach under basic conditions. The method consists of two steps: condensation of 2-bromoprop-2-enyl- or 2-propargylcyclohexanone with alcohols, amines, or amino alcohols, followed by base treatment (Scheme 1). Phenolic ethers and N-phenylated polyalkyl aromatic compounds are shown to be in the scope of the demonstrated reaction (Table). The proposed mechanism suggests that the unsaturation in another part of the molecule (propargyl-group equivalent) is transferred into the cyclohexane ring to yield a benzene ring through a series of prototropic shifts.