Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2-(2-Bromoprop-2-enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’

✍ Scribed by Emre Y. Yazıcıoğlu; İdris M. Akhmedov; Cihangir Tanyeli

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 264 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890124

✦ Synopsis

Abstract

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.