Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’ |
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Authors: | Emre Y Yazıcıoğlu İdris M Akhmedov Cihangir Tanyeli |
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Institution: | 1. Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey, (phone: +90?312?2103222;2. fax: +90?312?210?3200);3. Z. Khalilov 23, Baku State University, 370148 Baku, Azerbaijan |
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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. |
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Keywords: | Aromatization Cyclohexanones 2‐(2‐bromoprop‐2‐enyl)‐ Alcohols amino Benzenes alkyl‐ ‘ Intramolecular Unsaturation Transfer’ |
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