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

Yazicioglu, Emre Y.
Akhmedov, Idris M.
Tanyeli, Cihangir
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.